- The improvement of photovoltaic performance of quinoline-based dye-sensitized solar cells by modification of the auxiliary acceptors
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Three new dyes containing diphenylamine as electron donor, benzene (BIM1), benzothiadiazole (BTD) (BIM2) and N-ethylhexylbenzotriazole (BTZ) (BIM3) as auxiliary electron acceptors, quinoline as π-bridge and cyanoacrylic acid as anchoring group were synthesized in D-A-π-A structure for use in dye-sensitized solar cells (DSSCs). The optical, electrochemical, theoretical and photovoltaic methods were performed to understand the auxiliary acceptor influence on the performance of these dyes. Compared to the other dyes, the DSSC with dye BIM3 slightly increases the open circuit voltage (Voc) owing to the retardation of charge recombination by BTZ. However, replacement of benzene or BTZ by BTD unit causes a large red shift of the absorption spectra, leading BIM2 cell to produce the highest short circuit current density (Jsc). Thus, among the three D-A-π-A dyes, BIM2 is determined to be the most efficient dye, which reached a Voc of 0.627 V and Jsc of 11.53 mA cm–2, corresponding to an overall power conversion efficiency of 5.21 % in the presence of chenodeoxycholic acid (CDCA) as the coadsorbent. These results suggest that the insertion of benzothiadiazole as auxiliary acceptor into quinoline-based D-A-π-A dyes can effectively improve photovoltaic performance of DSSCs.
- ?i?man, ?lkay,Arkan, Burcu,Arslan, Bar?? Se?kin,Avc?, Davut,Derin, Yavuz,Gezgin, Merve,Nebio?lu, Mehmet,Tutar, Ahmet
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- Synthesis of novel halogenated heterocycles based on o‐phenylenediamine and their interactions with the catalytic subunit of protein kinase ck2
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Protein kinase CK2 is a highly pleiotropic protein kinase capable of phosphorylating hundreds of protein substrates. It is involved in numerous cellular functions, including cell viability, apoptosis, cell proliferation and survival, angiogenesis, or ER‐stress response. As CK2 activity is found perturbed in many pathological states, including cancers, it becomes an attractive target for the pharma. A large number of low‐mass ATP‐competitive inhibitors have already been developed, the majority of them halogenated. We tested the binding of six series of halogenated heterocyclic ligands derived from the commercially available 4,5‐dihalo‐benzene‐1,2‐diamines. These ligand series were selected to enable the separation of the scaffold effect from the hydrophobic interactions attributed directly to the presence of halogen atoms. In silico molecular docking was initially applied to test the capability of each ligand for binding at the ATP‐binding site of CK2. HPLC‐derived ligand hydrophobicity data are compared with the binding affinity assessed by low‐volume differential scanning fluorimetry (nanoDSF). We identified three promising ligand scaffolds, two of which have not yet been described as CK2 inhibitors but may lead to potent CK2 kinase inhibitors. The inhibitory activity against CK2α and toxicity against four reference cell lines have been determined for eight compounds identified as the most promising in nanoDSF assay.
- Maciejewska, Agnieszka Monika,Paprocki, Daniel,Poznański, Jaros?aw,Speina, El?bieta,Winiewska‐szajewska, Maria
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supporting information
(2021/06/09)
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- Fluorescence emission enhancement of a T-shaped benzimidazole with a mechanically-interlocked ‘suit’
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A fluorescent T-shaped benzimidazole was successfully designed and interlocked in a bicyclic macrocycle to form a suit[1]ane through supramolecular templated-synthesis. Compared with the bare fluorophore, suit[1]ane requires nearly two times the concentration to initialize the aggregation-caused quenching effect in solution. Furthermore, an 8-fold higher solid-state fluorescence quantum yield (21.7%) is also achieved. By taking advantage of mechanical bonding and molecular packing, such fluorescence emission enhancement through formation of a suitane opens the way to new complex fluorescent materials.
- Xu, Houyang,Lin, Meng-Di,Yuan, Jun,Zhou, Baiyang,Mu, Yingxiao,Huo, Yanping,Zhu, Kelong
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supporting information
p. 3239 - 3242
(2021/04/06)
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- Synthesis and Characterization of Acid-Responsive Luminescent Fe(II) Metallopolymers of Rigid and Flexible Backbone N-Donor Multidentate Conjugated Ligands
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In this report we have disclosed the syntheses and properties of two new conjugated organic moieties bearing the same coordination sites but possessing different backbone rigidities and rotational flexibilities. Two new metallopolymers have been synthesized from the corresponding ligands under identical reaction conditions, and they have been thoroughly characterized through different techniques to understand the effect of backbone rigidity on the evolution of different properties in these metallopolymers. A FESEM micrograph of the rigid metallopolymer confirms the formation of a rigid nanorod type structure, while long agglomerated nanofiber strands are visible on the substrate in the case of the flexible analogue. All of the newly synthesized materials are fluorescence active. An Fe(II) metallopolymer of the flexible ligand showed huge changes in emission properties in the presence of different acids and showed a possibility of it being used as a thin film acid vapor sensor. All of the materials showed reversible electrochemical activity, and both of these polymers have shown electroluminescence when an appropriate potential is applied.
- Kumar, Anil,Bawa, Shubham,Ganorkar, Kapil,Ghosh, Sujit Kumar,Bandyopadhyay, Anasuya
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p. 1746 - 1757
(2020/02/05)
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- Between Aromatic and Quinoid Structure: A Symmetrical UV to Vis/NIR Benzothiadiazole Redox Switch
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Reversibly switching the light absorption of organic molecules by redox processes is of interest for applications in sensors, light harvesting, smart materials, and medical diagnostics. This work presents a symmetrical benzothiadiazole (BTD) derivative with a high fluorescence quantum yield in solution and in the crystalline state and shows by spectroelectrochemical analysis that reversible switching of UV absorption in the neutral state, to broadband Vis/NIR absorption in the 1st oxidized state, to sharp band Vis absorption in the 2nd oxidized state, is possible. For the one-electron oxidized species, formation of a delocalized radical is confirmed by electron paramagnetic resonance spectroelectrochemistry. Furthermore, our results reveal an increasing quinoidal distortion upon the 1st and 2nd oxidation, which can be used as the leitmotif for the development of BTD based redox switches.
- Rietsch, Philipp,Sobottka, Sebastian,Hoffmann, Katrin,Popov, Alexey A.,Hildebrandt, Pascal,Sarkar, Biprajit,Resch-Genger, Ute,Eigler, Siegfried
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p. 17361 - 17365
(2020/12/01)
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- Constructing fused bis-isatins from pyrroloindoles using direct oxidation approach and re-visiting indophenine reaction
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Two novel electron accepting bis-isatins, having fused bis-lactam rings have been synthesized from corresponding pyrroloindoles 7 and 14 by one-pot direct oxidation approach involving oxidant NBS with or without co-oxidant TBHP in DMF/CHCl3. Synthesized fused bis-isatins 8 and 15 are extensively studied for thermal, photophysical, electrochemical and thin-film morphological properties and are found to have characteristic properties like solid-solid transitions, visible light absorption, lowered FMO energy levels (LUMOs below ?4.1 eV and HOMOs below ?5.9 eV) as well as oriented packing of molecules in the film state. The famous indophenine reaction is re-visited with fused bis-isatins to form conjugated polymers P-1 and P-2, having quinoidal pyrroloindole dione units. The polymers are studied for thermal, photophysical, electrochemical and thin-film morphological properties indicating sufficiently high thermal stability (up to 200 °C), extended absorptions up to near IR region, lowered FMO energy levels (LUMOs below ?4.3 eV and HOMOs below ?5.8 eV) and amorphous nature of polymer films.
- Bhanvadia, Viraj J.,Choudhury, Anwesha,Iyer, Parameswar Krishnan,Patel, Arun L.,Zade, Sanjio S.
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- Design and development of dithienopyrrolobenzothiadiazole (DTPBT)-based rigid conjugated polymers with improved hole mobilities
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Donor-acceptor integrated ladder-type dithienopyrrolobenzothiadiazole (DTPBT)-based conjugated building blocks have been used to develop rigid conjugated polymers by copolymerizing them with synthesized ladder-type indoloquinoxaline, π-extended isoindigo and π-extended 2,1,3-benzothiadiazole-based conjugated building blocks. Structural aspects of synthesized building blocks are studied by single-crystal X-ray diffraction, which revealed the co-planar structure of indoloquinoxaline-scaffold while twisted but intramolecularly hydrogen-bonded structures of π-extended isoindigo- and 2,1,3-benzothiadiazole-scaffolds with number of intermolecular non-bonding interactions. The synthesized DTPBT-based conjugated polymers P-1, P-2 and P-3 are studied for photophysical and electrochemical properties and are found to have moderate to good visible light absorptivity with HOMO energy levels below ?5.0 eV. The X-ray diffraction studies indicate strong π?π stacking interactions induced face-on arrangement of polymer chains respective to the substrate. Polymers show π?π stacks promoted high space-charge limited current (SCLC) hole mobilities ranging between 5.6 × 10?4 –1.3 × 10?3 cm2V?1s?1. The obtained SCLC hole mobility data in tandem with the studied structural aspects of monomers and morphological aspects of polymers, suggest that the combination of ladder-type DTPBT-scaffolds (capable of intermolecular π?π interactions) with non-ladder-type planar and structurally rigid π-extended conjugated scaffolds (capable of intermolecular π?π and other non-bonding interactions) is beneficial for getting good hole mobilities.
- Bhanvadia, Viraj J.,Machhi, Hiren K.,Soni, Saurabh S.,Zade, Sanjio S.,Patel, Arun L.
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- Observation of Microheterogeneity in Highly Concentrated Nonaqueous Electrolyte Solutions
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The development of models to describe structure and dynamics of nonaqueous electrolyte solutions is challenging, and experimental observations are needed to form a foundation. Here, neutron scattering is used to probe molecular dynamics in nonaqueous organic electrolytes. Two solutions were compared: One contained symmetrical electrolyte molecules prone to crystallize, and one contained desymmetrized electrolyte molecules preferring disordered states. For the latter, calorimetry and neutron data show that a disordered fluid persists to very low temperatures at high concentrations. Upon heating, localized cold crystallization occurs, leading to burst nucleation of microcrystalline solids within fluid phases. Our findings indicate molecular clustering and point to solvation inhomogeneities and molecular crowding in these concentrated fluids.
- Robertson, Lily A.,Li, Zhixia,Cao, Yu,Shkrob, Ilya A.,Tyagi, Madhusudan,Smith, Kyle C.,Zhang, Lu,Moore, Jeffrey S.,Zhyang
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supporting information
p. 8041 - 8046
(2019/06/04)
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- Two-dimensional metal organic complex containing thiazole functional groups, and preparation method and application thereof
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The invention discloses a two-dimensional metal organic complex containing thiazole functional groups, and a preparation method and application thereof. According to a technical scheme in the invention, the preparation method comprises the following steps: adding Pb(NO), 4,4'-(benzothiazolyl-4,7-disubstituted)-dibenzoic acid and a solvent, namely N,N-dimethylformamide into a container, and carrying out stirring for 30 minutes at normal temperature until the materials are uniformly mixed; sealing the container, putting the container into an oven, and keeping the container at a temperatureof 368 K for 1 day; carrying out slow cooling to room temperature to obtain a yellow transparent rod-like crystal; and washing the yellow transparent rod-like crystal with N,N-dimethylformamide, andcarrying out filtering and drying to obtain a target product (Pb-btdb). The prepared two-dimensional metal organic complex containing the thiazole functional groups is used as a catalyst and can efficiently catalyze cycloaddition conversion of carbon dioxide and epoxide to prepare cyclic carbonate.
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Paragraph 0049; 0052
(2020/07/13)
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- High-performing D-π-A-π-D benzothiadiazole-based hybrid local and charge-transfer emitters in solution-processed OLEDs
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Transforming triplet excitons into singlet excitons is a topic of great interest to material scientists in order to surpass the exciton utilization efficiency (EUE) limit of 25% in electro-fluorescent devices. Towards this goal, the donor-acceptor strategy of molecular design has been proven to be an effective approach to obtain high electroluminescence (EL) efficiency. In this context, herein, we report two benzothiadiazole (BTD)-based donor-acceptor π-conjugated fluorescent molecules, 1 and 2, which exhibited an external quantum efficiency (EQE) as high as 7.0% and 8.1%, respectively, in solution-processed doped green OLED devices. The observed high photoluminescence (PL) quantum yield of 81% for 1 and 85% for 2 corroborate the high EUE values of 43% and 48%, respectively, exceeding the traditional limit (25%), hence suggest the utilization of triplet excitons. The reported emitters combine two parameters, i.e. high PL efficiency and high EUE, which are of key importance to harvest maximum EL in OLED devices. Based on the photophysical (solvatochromic experiment) and quantum chemical calculations, the impacts of the D-π-A-π-D molecular design on the regulation of the locally excited and charge transfer components were revealed, which explained the observed high EQE (>5%) and EUE (>25%) values for the BTD-based emitters. The development of emitters with a hybrid local and charge transfer state in combination with the 'hot exciton' mechanism is an important strategy to produce highly efficient fluorescent-emitter materials. Besides the impressive EL properties of the emitters, the studied compound 1 as a chemosensor showed the selective sensing of metal cation (Fe2+) and anion (I-) together with the staining agent of Hibiscus rosa-sinensis pollen grains.
- Bala, Indu,Cheng, Chien-Hong,De, Joydip,Devi, Manisha,Jayakumar, Jayachandran,Jou, Jwo-Huei,Kailasam, Kamalakannan,Pal, Santanu Kumar,Singh, Nitya,Yadav, Rohit Ashok Kumar
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supporting information
p. 17009 - 17015
(2020/12/30)
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- Differently substituted benzothiadiazoles as charge-transporting emitters for fluorescent organic light-emitting diodes
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Carbazolyl- and 1,2,3,4-tetrahydrocarbazolyl-substituted benzothiadiazoles were prepared by Pd-catalyzed Buchwald-Hartwig and Heck reactions. Photophysical, electrochemical, thermal, charge-transporting properties, and performance in organic light emitting diodes (OLEDs) of the derivatives with donor-π-acceptor-π-donor and donor-acceptor-donor structures are discussed. Photo- and electroluminescent properties of the studied compounds of carbazole and benzothiadiazole are very sensitive to their molecular structures. Their glass transition temperatures range from 145 to 191 °C. Investigation of photophysical properties revealed importance of intramolecular twisting on excited state deactivation. Emission of dilute solutions of the compounds in nonpolar solvents appears in the orange region with fluorescence quantum yields up to 0.6.4,7-(Di (1,2,3,4-tetrahydro)carbazolyl)-[2,1,3]-benzothiadiazole demonstrates phosphorescence and delayed fluorescence at room temperature. Solid-state ionization potentials of the materials range from 5.64 to 5.82 eV. The layer of 4,7-(di (tert-butyl)carbazolyl)-[2,1,3]-benzothiadiazole shows high hole drift mobility of 1.7 × 10?3 cm2/V·s at an electric field of 5.3 × 105 V/cm and relatively high electron drift mobility of 5.7 × 10?5 cm2/V·s at an electric field of 5.8 × 105 V/cm. Red OLEDs based of singlet emission with maximum external quantum efficiency values of 1.3 and 0.13% were achieved using new emitters. Much better electroluminescent performance was observed for the compound having donor-acceptor-donor structure relative to the compound with donor-π-acceptor-π-donor structure.
- Gudeika, Dalius,Miasojedovas, Arunas,Bezvikonnyi, Oleksandr,Volyniuk, Dmytro,Gruodis, Alytis,Jursenas, Saulius,Grazulevicius, Juozas V.
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p. 217 - 225
(2019/03/26)
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- Effect of the linkages on the self-assembly and photophysical properties of 4,7-diphenyl-2,1,3-benzothiadiazole-based luminescent polycatenars
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Three series of 4,7-diphenyl-2,1,3-benzothiadiazole (DBTD)based polycatenars containing a central 4,7-diphenyl-2,1,3-benzothiadiazole moiety connected to 3,4,5-trialkoxyl benzene units at both ends through ether (-OCH2-), ester (-OOC-)or amide (-HNCO-)linkages were synthesized via Suzuki coupling reaction as key step. The polarities of the linkages had great effect on their self-assembly and photophycial properties. Both ether and amide compounds were mesogens, while the ester compounds were non-mesogens. The ether compounds displayed Colhex/p6mm phases, while the amide compound displayed two kinds of columnar phases i.e. columnar rectangular phase with p2mm and columnar hexagonal phase with p6mm lattices depending on temperature. The column phases could be aligned in electric field or under mechanical shearing. The ether and amide compounds showed the significant red-shifted maximum absorption and emission. In the solid and gel states, both ether and amide compounds were yellow luminescence, while ester compounds were green luminescence.
- Hu, Jinliang,Xiao, Yulong,Chang, Qing,Gao, Hongfei,Cheng, Xiaohong
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- Effective design of A-D-A small molecules for high performance organic solar cells via F atom substitution and thiophene bridge
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Three novel small molecules with acceptor-donor-acceptor (A-D-A) configuration, SBDT1, SBDT2 and SBDT3, where 4,8-bis(octyloxy)benzo[1,2-b:4,5-b′]dithiophene (BDT) as the electron-donating core connecting to thiophene-substituted benzothiadiazole (BT) as electron-withdrawing are reported. The effects of fluorine atoms on the photophysical properties by introducing different fluorine atoms into the benzothiadiazole unit were investigated. These SBDTs exhibit good thermal stability, excellent panchromatic absorption in solution and film. SBDT2 and SBDT3 with fluorine-substituted BT possess a relatively deeper the highest occupied molecular orbital (HOMO). These A-D-A type molecules were treated as donor and PC71BM as acceptor in bulk heterojunction (BHJ) small-molecule organic solar cells (SMOSCs). Among them, device based on SBDT2 gave the best device performance with a PCE of 5.06% with Jsc of 10.56 mA/cm2, Voc of 0.85 V, fill factor (FF) of 56.4%. These studies indicate that proper incorporation of fluorine atoms is an effective way to increase the efficiency of organic solar cells.
- He, Anwang,Qin, Yuancheng,Dai, Weili,Zhou, Dan,Zou, Jianping
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supporting information
p. 2263 - 2265
(2019/08/26)
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- Synthesis and characterization of non-symmetrical photoswitchable DTE(OMe) sensitizers
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DTE-BODIPY 2 and BTD-DTE 3 were designed for reversible light modulation of electron- and energy-transfer processes on TiO2, and showed almost complete ring closure. In BTD-DTE 3 the BTD is an acceptor group in the open form (OF), and an energy donor group in the closed form (CF), but this property is depending on the solvent. Quantum yields for ring closure decreased (BTD-DTE 3: factor 5; DTE-BODIPY 2: factor 12) compared to DTE 1, because of π-system elongation in OFs, and also cycloreversion quantum yields became smaller (BTD-DTE 3: factor 1.4; DTE-BODIPY 2: factor 2.2).
- Ziebart, Nandor,Schroeer, Pierre,Rueck-Braun, Karola
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supporting information
p. 5561 - 5566
(2018/05/29)
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- Selenium-containing near-infrared organic semiconductor as well as preparation method and application thereof
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The invention relates to a selenium-containing near-infrared organic semiconductor as well as a preparation method and application of the organic semiconductor to photothermal therapy of tumor. The organic semiconductor is characterized in that selenium atoms are introduced into benzothiadiazole units; the selenium atoms have high polarizability; the spectrum moves to a long-wavelength direction;through the organic semiconductor, an organic nano material with absorption wavelength (an ultraviolet absorption wavelength reaches up to 906nm, and a fluorescence emission wavelength reaches up to 1040nm) in a near-infrared area is obtained by a re-precipitation method; the nano reagent has high photothermal conversion efficiency, excellent water dispersibility, excellent tumor tissue targetingproperty and high biological compatibility, can be applied to therapy of tumor cells and living organisms, and is capable of effectively inhibiting the growth of the tumor cells and effectively inhibiting metastasis of tumor cells so as to achieve the photothermal therapy effect of the tumor, so that the nano reagent has great application prospects in the field of tumor therapy.
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Paragraph 0043; 0045; 0046
(2018/07/06)
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- Synthesis, characterization and properties of aryl-fused bis-BN dihydropyrenes
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A series of aryl-fused bis-BN dihydropyrenes were synthesized via amino-directed borylation reaction. The aryl-fused bis-BN dihydropyrenes showed blue emission, and their physical properties could be finely tuned through varying the fused aryl rings. In particular, their response towards fluoride anions was greatly dependent on the nature of the fused aryl rings.
- Zhang, Jinyun,Liu, Fude,Sun, Zhe,Li, Chenglong,Zhang, Qian,Zhang, Chen,Liu, Zhiqiang,Liu, Xuguang
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supporting information
p. 8178 - 8181
(2018/07/29)
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- Synthesis, characterization and electrochemistry of polycyclic fused aromatic pyrroles and their conjugated polymers
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Polycyclic fused aromatic pyrrole-based compounds, benzodipyrrole, naphthobipyrrole and their alkylated derivatives, were synthesized and studied electrochemically. Amongst these, naphthobipyrrole having a tetracyclic fused aromatic structure was electrochemically polymerized to give the homopolymer of naphthobipyrrole, poly(naphthobipyrrole), indicating good reactivity of α,α′-pyrrolic positions towards oxidative coupling. As a strategic approach towards the synthesis of copolymers, naphthobipyrrole was copolymerized with arylaldehyde to afford poly(arylmethylene naphthobipyrrole) by exploring the reactivity of β,β′-pyrrolic positions. Moreover, optical and electrochemical studies showed that the copolymer possessed a low optical bandgap and an elevated HOMO level. The scan rate dependent cyclic voltammetry studies of the copolymer film showed the formation of an electroactive material.
- Bhanvadia, Viraj J.,Mankad, Yash J.,Patel, Arun L.,Zade, Sanjio S.
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supporting information
p. 13565 - 13572
(2018/08/21)
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- Effect of heteroatom exchange (S/Se) in the mesomorphism and physical properties of benzochalcogenodiazole-based liquid crystals
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In order to investigate the effect on the structure-property relationship by the exchange of sulfur atom by selenium, a new series of fluorescent calamitic liquid crystals based on 4,7-disubstituted-2,1,3-benzoselenadiazole was successfully synthesized and characterized. The mesomorphic properties were studied by differential scanning calorimetry, polarized optical microscopy and X-ray diffraction. Thermal properties have evidenced the influence of changing sulfur by selenium atom in the formation of liquid crystalline phases and mesomorphism range. Photophysical studies were performed in chloroform solution, where these compounds displayed strong orange luminescent under UV light, with relevant quantum yields (ΦF = 0.14–0.16) and greater solvatochromic dependence. Electrochemical studies showed oxidation and reduction patterns similar to 2,1,3-benzothiadiazoles analogues, however presenting lower band gap.
- Regis, Elias,Aguiar, Leonardo de O.,Tuzimoto, Patricia,Girotto, Edivandro,Frizon, Tiago E.,Dal Bó, Alexandre G.,Zapp, Eduardo,Marra, Raphael,Gallardo, Hugo,Vieira, André A.
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p. 109 - 116
(2018/05/07)
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- Mesogenic D-A fluorophores based on cyanovinyl and benzothiadiazole
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A series of donor-acceptor fluorophores containing the biscyanovinyl dithienebenzothiadiazole central unit with 4-alkoxyphenyl groups at both sides were synthesized. These compounds can display smectic C and hexagonal columnar mesophases in their bulk states, and aggregate into organogels as well as cubic or needle crystals in organic solvents. These cubic or needle crystals exhibit optical waveguide behavior. Additionally, these compounds can exhibit broad absorption up to 625 nm with a narrow band gap of 1.79 eV. The fluorescence emission of these compounds in CHCl3 can be quenched upon addition of C70. Furthermore, these compounds can detect Cu2+ among a series of cations.
- Zhang, Bei,Xiao, Yulong,Fang, Haipeng,Gao, Hongfei,Wang, Fuke,Cheng, Xiaohong
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supporting information
p. 16709 - 16716
(2018/10/24)
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- A fast response of nitric oxide near-infrared probe and its preparation and biological applications (by machine translation)
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The invention relates to a fast response of nitric oxide near-infrared probe and its preparation and biological application, the structure shown in formula (I), which belongs to the field of organic fluorescent probe. This invention is designed and has synthesized a kind of fast response of the near-infrared nitric oxide probe. The probe is after NO response with near-infrared emission. In vitro experimental study shows that, probe and NO fast reaction speed. In the physiological conditions (pH 7.4) next, probe stability, and to NO has higher sensitivity, selectivity and interference. Biological experimental study shows that, probe not only can be applied to the cell in the level of endogenous NO detection, can also be applied to PD cell and Drosophila brain model in NO level of detection. These results indicate that, the probe has a relatively high specificity, selectivity, stability, which may be applied to the early diagnosis of Parkinson's disease. (by machine translation)
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Paragraph 0044; 0047-0048
(2018/12/14)
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- Molecular-level architectural design using benzothiadiazole-based polymers for photovoltaic applications
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A series of low band gap, planar conjugated polymers, P1 (PFDTBT), P2 (PFDTDFBT) and P3 (PFDTTBT), based on fluorene and benzothiadiazole, was synthesized. The effect of fluorine substitution and fused aromatic spacers on the optoelectronic and photovoltaic performance was studied. The polymer, derived from dithienylated benzothiodiazole and fluorene, P1, exhibited a highest occupied molecular orbital (HOMO) energy level at -5.48 eV. Density functional theory (DFT) studies as well as experimental measurements suggested that upon substitution of the acceptor with fluorine, both the HOMO and lowest unoccupied molecular orbital (LUMO) energy levels of the resulting polymer, P2, were lowered, leading to a higher open circuit voltage and short circuit current with an overall improvement of more than 110% for the photovoltaic devices. Moreover, a decrease in the torsion angle between the units was also observed for the fluorinated polymer P2 due to the enhanced electrostatic interaction between the fluorine substituents and sulfur atoms, leading to a high hole mobility. The use of a fused π-bridge in polymer P3 for the enhancement of the planarity as compared to the P1 backbone was also studied. This enhanced planarity led to the highest observed mobility among the reported three polymers as well as to an improvement in the device efficiency by more than 40% for P3.
- Viswanathan, Vinila N.,Rao, Arun D.,Pandey, Upendra K.,Kesavan, Arul Varman,Ramamurthy, Praveen C.
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supporting information
p. 863 - 873
(2017/06/21)
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- Series carbazole derivatives and application
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The invention discloses a preparation method of series carbazole derivatives and application thereof to organic light emitting diodes. A structural formula of the carbazole derivatives is shown as a formula I. Power efficiency and external quantum efficiency of organic electroluminescence devices prepared from the carbazole derivatives can be improved remarkably, service lives of orange or red light devices are prolonged, and a material synthesis and purification method is simple and suitable for large-scale production, so that the carbazole derivatives is an ideal selection for a light emitting material of the organic electroluminescence devices. Application of the organic electroluminescence diode material serving as a carrier transport material or singly serving as a light emitting material or serving as a main material in a light emitting layer is also protected.
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Paragraph 0059-0061
(2017/08/19)
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- A simple fluorene core-based non-fullerene acceptor for high performance organic solar cells
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A small molecule non-fullerene acceptor based on a fluorene core having a furan π-spacer and end capped with rhodanine (FRd2) is developed for solution processable bulk heterojunction organic solar cells (OSCs). The simplistic synthetic protocol reduces several reaction steps and hence production cost. Extended π-conjugation via furan units and the presence of electronegative rhodanine groups result in a power conversion efficiency of 9.4% in OSCs, which is the highest so far among these categories of molecules.
- Suman,Bagui, Anirban,Datt, Ram,Gupta, Vinay,Singh, Surya Prakash
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supporting information
p. 12790 - 12793
(2017/12/06)
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- Benzothiadiazole-based D-π-A-π-D fluorophores: Synthesis, self-assembly, thermal and photophysical characterization
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A symmetrical linear D-π-A-π-D hexacatenar compound with 2,1,3-benzothiadiazole as the acceptor core connected at its 4,7 position with phenylthienylethynyl spacers has been designed and synthesized. This compound displays liquid crystalline property with oblique columnar mesophase and forms an organogel in dichloromethane. The investigation of photophysical and electrochemical properties reveals that this compound can exhibit broad and strong absorption band at the range of 300–700 nm with a low energy gap in solid state, meanwhile it exhibits highly red fluorescent emission and large Stokes shifts.
- Fang, Haipeng,Gao, Hongfei,Wang, Tingyan,Zhang, Bei,Xing, Wei,Cheng, Xiaohong
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p. 190 - 198
(2017/08/22)
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- Fluorescent metal-organic frameworks for selective sensing of toxic cations (Tl3+, Hg2+) and highly oxidizing anions ((CrO4)2?, (Cr2O7)2?, (MnO4)?)
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The ligand 4,4′‐(benzothiadiazole‐4,7‐diyl)dibenzoic acid was synthesized and employed for the synthesis of two metal-organic framework (MOF) compounds, [Mn4(C20H10N2O4S)2(HCOO)4(DEF)2] (I; DEF=N, N′‐diethylformamide) and [Pb(C20H10N2O4S)(DMF)] (II; DMF=N,N′‐dimethylformamide). Single‐crystal structure studies revealed that compound I has a three‐dimensional structure and compound II has a two‐dimensional structure. The luminescent nature of the MOFs was gainfully employed as a probe for the detection of highly toxic metal ions such as Tl3+ and Hg2+. The detection limits were found to be in the parts per billion (ppb) level. The presence of an unsubstituted thiadiazole ring in the ligand appears to help in the detection of these highly toxic metal ions in solution as the metal ions interact with S, which was revealed by Raman spectroscopic studies. The compounds were also found to be good candidates for the detection of highly oxidizing anions such as chromate, dichromate, and permanganate, again in ppb levels of concentration in solution. Magnetic studies on compound I indicate antiferromagnetic behavior. The variable‐temperature electrical conductivity studies indicate a semiconducting nature with comparable behavior to well‐known semiconductors such as CdSe, ZnTe, and GaP.
- Jana, Ajay Kumar,Natarajan, Srinivasan
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p. 1153 - 1163
(2018/04/10)
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- Method for synthesizing 5-(8-bromine-2,3-diphenyl quinoxaline-5-yl) thiophene-2-formaldehyde
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The invention belongs to the technical field of organic electrofluorescent materials, and discloses a method for synthesizing 5-(8-bromine-2,3-diphenyl quinoxaline-5-yl) thiophene-2-formaldehyde. The method comprises the following steps: reacting 1,2-diaminobenzene sequentially with SOC12, bromine and the like to obtain intermediate 1; reacting 2-thiophenecarboxaldehyde sequentially with ethylene glycol, n-butyllithium and the like to obtain intermediate 2; and reacting the two intermediates with formic acid through a SUZUKI reaction product to obtain a target product having a molecular formula of C25H15BrN2OS. The synthesized product is orange solid powder, does not have mechanical impurity, and can be easily dissolved in THF and methylbenzene; and the synthesizing method is simple, and is easy for industrial production. A photovoltaic material prepared based on quinoxaline has the characteristic of relatively low HOMO energy level, is beneficial to improving the chemical stability of a finally prepared OLED material, and has a potential application value in the aspect of preparing photoelectrofluorescent devices or photoelectrofluorescent displays.
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Paragraph 0036; 0037; 0038; 0039
(2017/07/21)
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- Novel 2,1,3-benzothiadiazole derivatives used as selective fluorescent and colorimetric sensors for fluoride ion
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Two novel 2,1,3-benzothiadiazole derivatives, used as colorimetric and fluorescent sensors for fluoride ion were designed, synthesized and characterized. These sensors contained single hydrogen-bond functional groups, which acted as interacting sites for fluoride ion. Both sensors displayed a red color in dimethyl sulfoxide solution. Binding studies revealed that they showed noticeable colorimetric and fluorescent responses only to F- among the eight anions tested (F-, Cl-, Br-, I-, AcO-, H2PO4-, HSO4- and NO3-). 1H NMR titration proved that the interaction between compounds and fluoride ion: hydrogen bond at low fluoride ion concentration, deprotonation at high fluoride ion concentration. Moreover, those compounds showed high sensitivity and selectivity for fluoride ion by inhibiting the excited state intramolecular proton transfer processes, and the detective processes could be followed by direct visual observation.
- Wu, Jiefei,Lai, Guoqiao,Li, Zhifang,Lu, Yunxiang,Leng, Taohua,Shen, Yongjia,Wang, Chengyun
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p. 268 - 276
(2015/10/28)
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- Synthesis and self-assembly of luminescent hexacatenar molecules incorporating a 4,7-diphenyl-2,1,3-benzothiadiazole core
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A new polycatenar liquid crystal containing a 4,7-diphenyl-2,1,3-benzothiadiazole core and three alkoxy chains at each end has been synthesized via a copper-catalyzed azide-alkyne click reaction and investigated by polarizing microscopy, DSC, XRD scattering, SEM, UV-vis spectroscopy and photoluminescence measurements. This compound can self-assemble into an oblique columnar liquid crystalline phase in the bulk state and form organogels in different organic solvents. It shows highly fluorescent emission with large Stokes shift in solution and has binding selectivity to Li+ among a series of cations in DMSO-CH2Cl2 solution.
- Huang, Danxiang,Prehm, Marko,Gao, Hongfei,Cheng, Xiaohong,Liu, Yongsong,Tschierske, Carsten
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p. 21387 - 21395
(2016/03/08)
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- 2,1,3-Benzothiadiazole-based fluorophores. Synthesis, electrochemical, thermal and photophysical characterization
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Three photoactive compounds with π-extended conjugation based on the 2,1,3-benzothiadiazole unit were synthesized and characterized. The compounds exhibited absorption in the violet-blue region with molar absorptivity coefficients and radiative rate constants arising from spin and symmetry allowed 1ππ* electronic transitions. An emission located in the green region with a large Stokes shift was observed, which was most likely due to a charge-transfer mechanism in the excited state. In spin-coated films a dependence on the fluorescence emission intensity with the size of the alkoxy chain could be observed, where an effective non-radiactive channel seems to be present to deactivate the excited state. The thermal properties were analyzed by differential scanning calorimetry (DSC), and all final compounds exhibited a similar behavior with a crystal-isotropic liquid transition during the heating scan and isotropic liquid-crystal transition during the cooling process. Thermogravimetric analysis indicated a main thermal event with an initial decomposition temperature that was higher than 340?°C. The electrochemical characterization indicate that the compounds exhibited a reversible peak at ?1.48?V and an irreversible oxidation process at 0.94?V versus Ag/Ag+. The electrochemical band gap was calculated to be approximately 2.30?eV versus NHE. The spectroelectrochemical measurements demonstrated changes in the absorption spectra due to changes in the electronic structure of the conjugated molecules under oxidative and reductive potentials.
- Frizon, Tiago Elias Allievi,Valdivia Martínez, Julio César,Westrup, José Luiz,Duarte, Rodrigo da Costa,Zapp, Eduardo,Domiciano, Kelvin Guessi,Rodembusch, Fabiano Severo,Dal-Bó, Alexandre Gon?alves
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- Dibenzo [c, i] [1,10] O-phenanthroline and its derivatives and preparation method
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The invention discloses a dibenzo[c, i][1, 10]o-phenanthroline, its derivative and preparation method. The compound is characterized in that: two phenanthridines share a benzene ring, and the ortho-position of the nitrogen atom is equipped with a substituent group, which can be hydrogen, alkyl, phenyl or aryl. The preparation method includes: taking 4, 7-dibromobenzo[2, 1, 3]thiadiazole and 2-formyl phenylboronic acid or 2-acetyl(or arylformyl)phenylboronic acid pinacol ester as raw materials, carrying out Suzuki coupling reaction to obtain a series of 4, 7-di[2-formyl, 2-alkylformyl or arylformyl]benzo[2, 1, 3]thiadiazole, and finally carrying out reduction by sodium borohydride/cobalt chloride hexahydrate or lithium aluminum hydride and cyclization so as to obtain a series of dibenzo[c, i][1, 10]o-phenanthroline and its derivatives. The series of organic compounds provided by the invention broadens the scope of organic electroluminescent materials, and the preparation method provides a simple and convenient way for synthesis of phenanthroline series compounds. (formula).
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Paragraph 0031; 0032
(2017/01/26)
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- Synthesis, photophysical, electrochemical and single-crystal x-ray diffraction study of (Z)-2-phenyl-3-(5-(4-(thiophen-2-yl)benzo[c][1,2,5]thiadiazol-7-yl)thiophen-2-yl)acrylonitrile
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The optical characteristics, redox properties, thermogravimetric stability and single-crystal X-ray diffraction study of (Z)-2-phenyl-3-(5-(4-(thiophen-2-yl)benzo[c][1,2,5]thiadiazol-7-yl)thiophen-2-yl)acrylonitrile are examined using ultraviolet–visible spectrophotometry, cyclic voltammetry, thermal gravimetric analysis–diffraction scanning calorimetry analysis, single-crystal X-ray diffraction and density functional theory calculations. Evidently, the crystal structure of compound 6 is sustained by a number of weak nonconventional intermolecular forces of attraction such as C-H?…?N, C-H?…?π donor–acceptor interactions.
- Bhanvadia, Viraj J.,Patel, Heta A.,Sharma, Neha N.,Patel, Arun L.
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p. 1052 - 1061
(2016/07/16)
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- New photoactive D-π-A-π-D benzothiadiazole derivative: Synthesis, thermal and photophysical properties
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A new fluorophore containing a 2,1,3-benzothiadiazole unit containing alkylated tetrazoles terminal groups as electron donors connected through a π-conjugated system of type D-π-A-π-D was synthesized and electronically and electrochemically characterized. The compound in solution has an absorption maximum in the visible region (~417 nm) due to electronic transitions of type 1ππ?(ε ~ 104 M-1 cm-1) and intense fluorescence emission (ΦF ~ 0.65) located in the blue-green region depending on the solvent used with a Stokes' shift of ca. 75 nm. Evidences of intramolecular charge transfer character in the excited state was observed from the Lippert-Mataga correlation. The AFM images of the spin-coating depositions of compound 9 using chloroform as solvent on silicon substrate showed the formation of films with clusters. AFM images of the deposition of the acrylic thermoplastic resin doped with 0.05% of 9 showed the formation of a uniform, low-roughness film. Fluorescence emission was shown to be dependent on the method used for the formation of the films.
- Westrup, José Luiz,Oenning, Leonardo Werncke,Da Silva Paula, Marcos Marques,Da Costa Duarte, Rodrigo,Rodembusch, Fabiano Severo,Frizon, Tiago Elias Allievi,Da Silva, Luciano,Dal-Bó, Alexandre Gon?alves
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p. 209 - 217
(2016/02/03)
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- Supramolecular Synthesis Based on a Combination of Se?N Secondary Bonding Interactions with Hydrogen and Halogen Bonds
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Examination of the solid state structures of 2,1,3-benzoselenadiazole complexes with hydrogen or halogen bond donors has demonstrated that the 2,1,3-benzoselenadiazole molecules preferably form centrosymmetric dimers with use of [Se-N]2 supramolecular synthon, whereas the two remaining nitrogen atoms not involved in the [Se-N]2 supramolecular interactions can act as acceptors of hydrogen or halogen bonds. Cocrystallization of selenadiazoles with monofunctional hydrogen or halogen bond donors like pentafluorophenol, pentafluorobenzoic acid, or pentafluoroiodobenzene results in formation of binary discrete complexes. One- or two-dimensional aggregates based on selenadiazole [Se-N]2 dimers as building blocks were prepared using bifunctional hydrogen or halogen bond donors like resorcinol, tetrafluororesorcinol, tetrafluorohydroquinone, and 1,4-diiodotetrafluorobenzene. During the complexation of selenadiazoles with hydroquinone, anilic acid, or chloranilic acid a competition between Se?N and Se?O interactions resulted in breaking of the [Se-N]2 synthon.
- Eichstaedt, Katarzyna,Wasilewska, Aleksandra,Wicher, Barbara,Gdaniec, Maria,Po?oński, Tadeusz
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p. 1282 - 1293
(2016/03/12)
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- Effect of the functionalisation route on a Zr-MOF with an Ir-NHC complex for catalysis
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A new iridium N-heterocyclic carbene (NHC) metallolinker has been synthesised and introduced into a metal-organic framework (MOF), for the first time, via two different routes: direct synthesis and postsynthetic exchange (PSE). The two materials were compared in terms of the Ir loading and distribution using X-ray energy dispersive spectroscopy (EDS), the local Ir structure using X-ray absorption spectroscopy (XAS) and the catalytic activity. The materials showed good activity and recyclability as catalysts for the isomerisation of an allylic alcohol.
- Carson, Fabian,Martínez-Castro, Elisa,Marcos, Rocío,Miera, Greco González,Jansson, Kjell,Zou, Xiaodong,Martín-Matute, Belén
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supporting information
p. 10864 - 10867
(2015/06/30)
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- Organic solution-processible electroluminescent molecular glasses for non-doped standard red OLEDs with electrically stable chromaticity
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Abstract Organic light-emitting molecular glasses (OEMGs) are synthesized through the introduction of nonplanar donor and branched aliphatic chain into electroluminescent emitters. The target OEMGs are characterized by 1H NMR, 13C NMR, IR, UV-vis and fluorescent spectra as well as elemental analysis, TG and DSC. The results indicated that the optical, electrochemical and electroluminescent properties of OEMGs are adjusted successfully by the replacement of electron-donating group. The non-doped OLED device with a standard red electroluminescent emission is achieved by spin-coating the THF solution of OEMG with a triphenylamine moiety. This non-doped red OLED device takes on an electrically stable electroluminescent performance, including the stable maximum electroluminescent wavelength of 640 nm, the stable luminous efficiency of 2.4 cd/A and the stable CIE1931 coordinate of (x, y) = (0.64, 0.35), which is basically in accord with the CIE1931 coordinate (x, y) = (0.64, 0.33) of standard red light in PAL system.
- Bi, Xiaoman,Zuo, Weiwei,Liu, Yingliang,Zhang, Zhenru,Zeng, Cen,Xu, Shengang,Cao, Shaokui
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p. 865 - 875
(2015/06/30)
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- Thiadiazole quinoxaline-based copolymers with ~1.0 eV bandgap for ternary polymer solar cells
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A new strong electron-deficient acceptor unit, 4,9-bis(5-bromothiophen-2-yl)-6,7-bis(5-dodecylthiophen-2-yl)-[1,2,5]thiadiazolo[3,4-g]quinoxaline (TQxT), is designed. Three TQxT based new conjugated polymers have been further developed by alternating with benzo[1,2-b:4,5-b′]dithiophene or naphtho[1,2-b:5,6-b′]difuran. Featuring ultra low bandgaps of 1.03-1.10 eV, these polymers exhibit absorption spectra beyond near-infrared (NIR) region. The polymer:PC71BM (1:2) solar cells deliver a best power conversion efficiency (PCE) of 0.43%. The doping of 9 wt% PBDTT-TQxP into P3HT:PC71BM (1:2) blend, however, leads to a highest PCE of 3.58% for the resultant ternary solar cells, corresponding to ~22% improvement in comparison to 2.93% PCE for P3HT:PC71BM binary cells.
- Yu, Jiangsheng,An, Qiaoshi,Hai, Jiefeng,Nie, Xuemei,Zhou, Baojing,Zhang, Fujun,Tang, Weihua
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supporting information
p. 12 - 20
(2015/10/28)
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- Highly efficient and selective probes based on polycyclic aromatic hydrocarbons with trimethylsilylethynyl groups for fluoride anion detection
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Two polycyclic aromatic hydrocarbons bearing trimethylsilylethynyl groups were designed and synthesized as new colorimetric and ratiometric fluorescent probes for fluoride anion. Both probes exhibit high specific selectivity and sensitivity for F- compared to other anions. When F- is added to the solution of the probe, the trimethylsilyl substituents can be removed immediately, and the color of the solution changes from yellow to colorless under ambient light. Moreover, test papers based on the probes are prepared, which could be applied to detect F- in organic phase.
- Hu, Jinyang,Liu, Rui,Cai, Xiao,Shu, Mingliang,Zhu, Hongjun
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p. 3838 - 3843
(2015/06/02)
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- Third-order nonlinear optical properties of 3,4-ethylenedioxythiophene copolymers with chalcogenadiazole acceptors
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Two 3,4-ethylenedioxythiophene (EDOT) based low band gap donor-acceptor (D-A) conjugated copolymers were designed and synthesized via direct arylation, in which the HOMO-LUMO gaps were fine-tuned by the regular insertion of electron deficient units, 2,1,3-benzothiadiazole (BTZ) and 2,1,3-benzoselenadiazole (BTSe), respectively. Structural characterization was performed by FT-IR, 1H NMR and XPS. In order to investigate the variation in the energy band structure of the copolymers, quantum-chemical calculation using density functional theory was carried out. The alternating insertion of the chalcogenadiazole unit in the PEDOT (poly(3,4-ethylenedioxythiophene)) lowers the HOMO and LUMO energy levels. As a result, the polymers with a lower band gap compared to that of the homopolymer, PEDOT, were obtained. Optical and electrochemical results confirmed that BTSe is marginally superior to BTZ in EDOT based alternate donor-acceptor copolymers. The present experimental results correlate well with HSE06 level theoretical calculations compared to those with the B3LYP level. Z-scan experiments reveal that the copolymers exhibit a strong nonlinear absorption coefficient and a nonlinear refraction coefficient of the order 10-10 esu and the third-order nonlinear susceptibility is of the order of 10-11 esu. These findings indicated that the EDOT-chalcogenadiazole copolymers can be developed into excellent third-order nonlinear optical materials.
- Narayanan, Sona,Raghunathan, Sreejesh Poikavila,Poulose, Aby Cheruvathoor,Mathew, Sebastian,Sreekumar, Krishnapillai,Sudha Kartha, Cheranellore,Joseph, Rani
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p. 2795 - 2806
(2015/04/14)
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- Photodriven Multi-electron Storage in Disubstituted RuII Dppz Analogues
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Four derivatives of the laminate acceptor ligand dipyrido-[3,2-a:2′,3′-c]phenazine (dppz) and their corresponding ruthenium complexes, [Ru(phen)2(dppzX2)]2+, were prepared and characterized by NMR spectroscopy, ESI-MS, and elemental analysis. The new ligands, generically denoted dppzX2, were symmetrically disubstituted on the distal benzene ring to give 10,13-dibromodppz (dppz-p-Br), 11,12-dibromodppz (dppz-o-Br), 10,13-dicyanodppz (dppz-p-CN), 11,12-dicyanodppz (dppz-o-CN). Solvated ground state MO calculations of the ruthenium complexes reveal that these electron-withdrawing substituents not only lower the LUMO of the dppz ligand (dppz(CN)22dppz), but that the para disubstitution results in a lower LUMO than the ortho disubstitution (dppz-p-CN(dppz-o-CN), and dppz-p-Brdppz-o-Br). The validity of the calculations was confirmed experimentally using cyclic voltammetry. Of the complexes evaluated in this study, only the dicyanodppz complexes showed multiple dppz-based reductions prior to reduction of the phen ligands. The capacity to form singly and doubly reduced dppz-based anions at modest reduction potentials was confirmed using a combination of spectroelectrochemical and chemical titration methods. When subjected to photolysis with visible light in the presence of a sacrificial donor, such as triethylamine, both cyano complexes showed multi-electron reduction. The other complexes only show a single reduction.
- Aslan, Joseph M.,Boston, David J.,MacDonnell, Frederick M.
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p. 17314 - 17323
(2016/01/26)
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- Ethynylene-linked oligomers based on benzodithiophene: Synthesis and photoelectric properties
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Two conjugated ethynyl-linked oligomers, oligo(benzodithiophene-ethynylene- benzothiadiazole) (O1) and oligo(benzodithiophene-ethynylene-carbazole) (O2), were synthesized by Sonogashira coupling reaction. Their degrees of polymerization were 7 and 10, respectively. Their photophysical and electrochemical properties were investigated. O1 exhibitd two strong absorption bands at 404 nm and 483 nm, and O2 at 401 nm and 429 nm. The results of UV-Vis, cyclic voltammetry (CV) and theoretical calculations showed that O1 has a narrower band gap than O2. The conductivities of O1 and O2 were 1.05×10-15 and 6.98×10-16 S/cm, respectively, and would increase to 1.23×10-10 and 1.05×10 -10 S/cm after doping with iodine. Two oligomers based on benzodithiophene with different structures and energy levels. Copyright
- Jiang, Songyang,Ma, Yuwen,Wang, Yingyi,Wang, Chengyun,Shen, Yongjia
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p. 298 - 306
(2014/05/20)
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- Bright and photostable organic fluorescent dots with aggregation-induced emission characteristics for noninvasive long-term cell imaging
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Efficient long-term cell tracing in a noninvasive and real-time manner is of great importance to understand genesis, development, invasion, and metastasis of cancerous cells. Cell penetrating organic dots with aggregation- induced emission (AIE) characteristics are successfully developed as long-term cell trackers. The AIE dots enjoy the advantages of high emission efficiency, large Stokes shift, good biocompatibility, and high photostability, which ensure their good performance in long-term non-invasive in vitro cell tracing. Moreover, it is the first report that AIE dots exhibit certain permeability to cellular nucleus, making them attractive potential candidates for nucleus imaging. The AIE dots display superior performance compared to their counterparts of inorganic quantum dots, opening a new avenue in the development of fluorescent probes for monitoring biological processes. Encapsulation of orange-red fluorescent luminogens with aggregation-induced emission (AIE) characteristics in biocompatible matrix yields AIE dots with strong emission, large Stokes shift, good biocompatibility, and high photostability. Application of the AIE dots for in vitro cell tracing and nucleus imaging has been demonstrated using MCF-7 breast cancer cells as an example.
- Qin, Wei,Li, Kai,Feng, Guangxue,Li, Min,Yang, Zhiyong,Liu, Bin,Tang, Ben Zhong
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p. 635 - 643
(2014/03/21)
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- Small band gap D-π-A-π-D benzothiadiazole derivatives with low-lying HOMO levels as potential donors for applications in organic photovoltaics: A combined experimental and theoretical investigation
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In an attempt to develop small organic molecules with potential applications as donors in organic photovoltaic (OPV) devices, we have synthesized and characterized four novel benzothiadiazole (A) core structured D-π-A-π-D dyes featuring carbazole and benzocarbazole as donors (D) and fluorene and thiophene as spacers (π). The effects of the π-spacer units and variations in donor strength on the photophysical, electrochemical and thermal properties of the molecules have been investigated in detail. The replacement of fluorene by thiophene as a π-spacer promotes planarity, resulting in a larger bathochromic absorption shift, enhanced emission profiles and an enhanced intramolecular charge transfer (ICT) transition. The introduction of the benzocarbazole unit creates a low-lying HOMO level, as inferred from cyclic voltammetry studies. All the dyes exhibit remarkable thermal robustness. Theoretical calculations have been carried out to understand the structure-property relationships of the synthesized materials. The results obtained from the characterization methods reveal that the dyes with thiophene π-spacers show better optoelectronic properties compared to their fluorene counterparts. Solution-processable bulk-heterojunction devices with a structure of ITO/PEDOT:PSS (38 nm)/active layer/Ca (20 nm)/Al (100 nm) were fabricated using the materials investigated in this study as donors and (6,6)-phenyl C 61-butyric acid methyl ester (PC61BM) as an acceptor. A power conversion efficiency of 1.62% for the molecule with thiophene as a spacer and carbazole as donor/PC61BM was achieved for the preliminary photovoltaic devices under simulated AM 1.5 illumination (100 mW cm -2).
- Paramasivam, Mahalingavelar,Gupta, Akhil,Raynor, Aaron M.,Bhosale, Sheshanth V.,Bhanuprakash,Jayathirtha Rao
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p. 35318 - 35331
(2014/11/12)
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- Synthesis and photovoltaic properties of conjugated copolymers bearing bis(9,9-di(2-ethylhexyl)-9H-fluoren-2-yl)quinoxaline subunit with deep HOMO level
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A series of alternating copolymers (PT-BDFQx, PC-BDFQx and PBDT-BDFQx) have been synthesized bearing novel planar bis(9,9-di(2-ethylhexyl)-9H-fluoren-2-yl)quinoxaline (BDFQx) as acceptor unit, using benzo[1,2-b:4,5-b′]dithiophene (BDT), thiophene (T) and carbazole (C) as donor units via Stille or Suzuki coupling reactions. XRD characterization indicated that the presence of planar BDFQx unit (monomer 8) is favorable for the promotion of crystallization in the solid state and GPC results illustrated that the import of multiple chains in planar BDFQx unit raises the polymers molecular weight. Electrochemical measurement results suggested that three copolymers possess deep HOMO energy level of -5.50-5.77 eV. The polymer solar cell with structure of ITO/PEDOT:PSS (30 nm)/polymer: PCBM (60 nm)/Bphen (10 nm)/Ag (100 nm) exhibited the highest Voc of 0.80 V with PBDT-BDFQx as p-type polymer, while the best power conversion efficiency (PCE) of 0.9% was obtained using a blend of PBDT-BDFQx and PCBM(1:4) as active layer.
- Chen, Jing,Deng, Xianping,Yang, Daobin,Huo, Erfu,Chen, Yunqing,Huang, Yan,Lu, Zhiyun
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p. 5959 - 5966
(2015/02/19)
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- 1,2,5-Thiadiazole 2-oxides: Selective synthesis, structural characterization, and electrochemical properties
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A new general procedure for the selective synthesis of 1,2,5-thiadiazole 2-oxides (including fused derivatives) 8a,b,c,g,h from the reaction of vic-glyoximes with S2Cl2 and pyridine in acetonitrile was elaborated together with general procedure for the synthesis of 1,2,5-thiadiazoles 7a-i, 10, 12, and 14 from the same starting materials and reagents. Molecular structures of 3,4-dimethyl-1,2,5-thiadiazole 2-oxide 8a and [1,2,5]thiadiazolo[3,4-b]quinoxaline 10 were confirmed by single-crystal X-ray diffraction. Electrochemical properties of 1,2,5-thiadiazole 2-oxides 8 were studied by cyclic voltammetry and different behavior was observed for monocyclic and benzo-fused derivatives. With compounds 8g and 17, previously unknown deoxygenation of 2,1,3-benzothiadiazole 1-oxides was discovered by electrochemical reduction, and resulted 2,1,3-benzothiadiazoles 7g and 19 were detected in the forms of their radical anions by EPR spectroscopy combined with DFT calculations.
- Konstantinova, Lidia S.,Knyazeva, Ekaterina A.,Obruchnikova, Natalia V.,Vasilieva, Nadezhda V.,Irtegova, Irina G.,Nelyubina, Yulia V.,Bagryanskaya, Irina Yu.,Shundrin, Leonid A.,Sosnovskaya, Zhanna Yu.,Zibarev, Andrey V.,Rakitin, Oleg A.
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p. 5558 - 5568
(2015/03/30)
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- Donor-acceptor-integrated conjugated polymers based on carbazole[3,4-c:5,6- c]bis[1,2,5]thiadiazole with tight π-π Stacking for photovoltaics
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An original strategy to construct a new donor-acceptor (D-A)-integrated structure by directly imposing "pull" unit on the "push" moiety to form fused ring architecture has been developed, and poly{N-alkyl-carbazole[3,4-c:5,6-c]bis[1,2,5]thiadiazole-alt-thiophene} (PCBTT) with D-A-integrated structure, in which two 1,2,5-thiadiazole rings are fixed on carbazole in 3-, 4- and 5-, 6-position symmetrically and thiophene is used as bridge, has been synthesized. The interaction between pull and push units has fine tuned the HOMO/LUMO energy levels, and the resulting copolymer covers the solar flux from 300 to 750 nm. The interaction between pull and push units is worth noting that due to the fused five rings inducing strong intermolecular interaction, an extremely short π-π stacking distance of 0.32 nm has been achieved for PCBTT both in powder and solid states. This is the shortest π-π stacking distance reported for conjugated polymers. Additionally, an obvious intramolecular charge transfer and energy transfer from donor units to acceptor units have been detected in this D-A integration. A moderate-to-high open-circuit voltage of ~0.7 V in PCBTT:[6,6]-phenyl-C61 butyric acid methyl ester (PCBM) (w/w = 1/2) solar cells is achieved due to the low-lying HOMO energy level of PCBTT.
- Zha, Daijun,Chen, Lie,Wu, Feiyan,Wang, Hongming,Chen, Yiwang
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p. 565 - 574
(2013/08/24)
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- Syntheses and photoluminescence properties of rhenium(I) complexes based on dipyrido[3,2-a:2',3'-c]phenazine derivatives with carbazole moiety
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Four rhenium(I) complexes ReL1-ReL4 based on dipyrido[3,2-a:2',3'-c]phenazine (L1) and derivatives L 2-L4 ligands (L2: 10,13-dibromodipyrido[3,2-a:2',3'-c] phenazine, L3: 10-bromo-13-carbazolyl-dipyrido[3,2-a:2',3'-c] phenazine, L4: 10,13-dicarbazolyldipyrido[3,2-a:2',3'-c]phenazine) were synthesized and characterized. The Re(I) complexes ReL1-ReL4 show photoluminescent emissions at 556, 582, 637 and 662 nm, respectively, assigned to dp (Re)→p/ (diimine) MLCT phosphorescence in CH2CL 2 solution. The carbazole containing complexes ReL3 and ReL4, as compared to ReL1, exhibit higher luminescence. These observations imply that modification of diimine rhenium(I) carbonyl complexes with carbazole moiety would lead to efficient phosphorescent properties.
- Zhou, Yong-Hui,Wang, Zheng-Mei,Chen, Min-Dong,Guo, Sheng-Li,Zheng, You-Xuan
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p. 958 - 965
(2013/07/28)
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- Photophysical property trends for a homologous series of bis-ethynyl-substituted benzochalcogendiazoles
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We report on the preparation and photophysical property study of three homologous benzoheteroarene-ethynylene systems. Significant differences in the series' optical properties indicate a change in the HOMO-LUMO energy as the chalcogen is altered (O, S and Se) which we have examined using TD-DFT methods and shown to be attributable to modification of the HOMO energy. The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2012.
- Coombs, Benjamin A.,Lindner, Benjamin D.,Edkins, Robert M.,Rominger, Frank,Beeby, Andrew,Bunz, Uwe H. F.
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supporting information; experimental part
p. 550 - 553
(2012/05/04)
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- Synthesis and physico-chemical properties in aqueous medium of all possible isomeric bromo analogues of benzo-1H-triazole, potential inhibitors of protein kinases
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In ongoing studies on the role of the individual bromine atoms of 4,5,6,7-tetrabromobenzotriazole (TBBt) in its relatively selective inhibition of protein kinase CK2α, we have prepared all the possible two mono-, four di-, and two tri-bromobenzotriazoles and determined their physicochemical properties in aqueous medium. They exhibited a general trend of a decrease in solubility with an increase in the number of bromines on the benzene ring, significantly modulated by the pattern of substitution. For a given number of attached bromines, this was directly related to the electronic effects resulting from different sites of substitution, leading to marked variations of pK a values for dissociation of the triazole proton. Experimental data (pKa, solubility) and ab initio calculations demonstrated that hydration of halogenated benzotriazoles is driven by a subtle balance of hydrophobic and polar interactions. The combination of QM-derived free energies for solvation and proton dissociations was found to be a reasonably good predictor of inhibitory activity of halogenated benzotriazoles vs CK2α. Since the pattern of halogenation of the benzene ring of benzotriazole has also been shown to be one of the determinants of inhibitory potency vs some viruses and viral enzymes, the present comprehensive description of their physicochemical properties should prove helpful in efforts to elucidate reaction mechanisms, including possible halogen bonding, and the search for more selective and potent inhibitors.
- Wa?sik, Romualda,Wińska, Patrycja,Poznański, Jaros?aw,Shugar, David
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experimental part
p. 7259 - 7268
(2012/08/28)
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- D-A-D low band gap molecule containing triphenylamine and benzoxadiazole/benzothiadiazole units: Synthesis and photophysical properties
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Two D-A-D-type low band gap organic dyes based on triphenylamine and benzoxadiazole/benzothiadiazole, 4,7-Bis{5-{4-{2-[4-(N,N-diphenylamino)phenyl]- 1-nitrilethenyl}phenyl}-2-thienyl}-2,1,3-benzoxadiazole (BDNTBX) and 4,7-Bis{5-{4-{2-[4-(N,N-diphenylamino)phenyl]-1-nitrilethenyl}phenyl}-2-thienyl} -2,1,3-benzothiadiazole (BDNTBT) were successfully synthesized. The properties of two compounds were investigated by density functional theory (DFT) calculations, UV-vis absorption spectroscopy, cyclic voltammetry and fluorescence quenching experiment. The calculated ground-state geometries demonstrate intramolecular charge transfer (ICT) occurs in both molecules during the procedure of charge excitation from HOMO to LUMO. From the data in electrochemistry and fluorescence quenching experiments, the molecules reveal lower HOMO energy levels compared with that of P3HT and proper LUMO energy levels to obtain efficient charge separation with PCBM. Two synthesized compounds exhibit broad absorption range covering the whole visible spectral region. These photophysical and electrochemical properties call attention to that our materials are prospective candidates as donor materials for solution-processable organic photovoltaic cells.
- Zeng, Shaohang,Yin, Lunxiang,Jiang, Xueying,Li, Yanqin,Li, Kechang
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scheme or table
p. 229 - 235
(2012/09/07)
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