- Alkyl-thiophene Functionalized D-π-A Porphyrins for Mesoscopic Solar Cells
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An alkyl-thiophene functionalized D-π-A porphyrin (LW16) is designed and synthesized for dye-sensitized solar cells (DSSCs). Two hexyl-thiophene groups are attached to the meta-position of each meso-phenyl with a motivation to increase the light-harvesting ability as well as retarding the aggregation of porphyrins dyes. For comparison, none-alkyl substituted (LW14) and octyloxy substituted (LW15) porphyrin dyes are also synthesized to fully investigate the influence of porphyrin chromophore modification. These porphyrins present similar spectrum while the oxidation potentials vary as the functionalized group changes from the meta-position to ortho-position. The DSSCs based on the alkyl-thiophene functionalized (LW16), none-alkyl substituted (LW14), and octyloxy substituted (LW15) porphyrins can be achieved a power conversion efficiency of 8.5%, 6.9%, and 8.2% using I-/I3-redox electrolyte under full sunlight irradiation (AM 1.5 G, 100 mW cm-2), respectively. It is found that by tailoring the porphyrin chromophore with hexyl-thiophenes, the photocurrent of the corresponding devices could be increased without sacrifice the photovoltage. Detailed investigation, including spectroscopy, electrochemical and transient photovoltage decay measurement, provides general influence of π-conjugation extension at the meso-position onto the optoelectronic features of porphyrins dyes.
- Lu, Jianfeng,Liu, Shuangshuang,Shen, Yan,Xu, Jie,Cheng, Yibing,Wang, Mingkui
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- Synthesis, photoluminescence, and electroluminescence characterization of double tetraphenylethene-tethered BODIPY luminogens
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Three double tetraphenylethene (TPE)-tethered 4-difluoro-4-bora-3a,4a-diaza-s-indance (BODIPY) fluorophores, 35TPEBODP, 88TPEBODP, and 26TPEBODP, have been synthesized and characterized. The green 35TPEBODP with deep red fluorescence shows serious thermal decomposition in the purification process of sublimation, which prohibits its test for an organic light-emitting diode (OLED) fabricated by the vacuum–thermal evaporation process. The tethered TPE is attached to BODIPY at three different positions, resulting in different photoluminescence (emission wavelength and quantum yield) and electroluminescence (EL). Different from TPE-tethered BODIPY fluorophores reported in literature, none of the BODIPY fluorophores studied here exhibits aggregation-induced emission (AIE), aggregation-induced enhanced emission (AIEE), or twisted intramolecular charge transfer (TICT) characteristics. Although solution (10?5 M THF) photoluminescence quantum yields (?s) are relatively high at 78%, 68%, and 86% for 35TPEBODP, 88TPEBODP, and 26TPEBODP, respectively, which are all higher than 41% of PhBODP (a non-TPE-tethered BODIPY), the ? is significantly decreased to 1–6% in 5 wt% dopant polystyrene thin film or as a solid powder, except for 13% of 26TPEBODP. Therefore, due to the low ? of dopant thin film or solid powder, either dopant or nondopant OLEDs exhibit inferior external quantum efficiency (EQE) and intensity of EL. The best OLED in this study is the 26TPEBODP device, and its EQE reaches 1.3%, and the highest EL intensity is approximately 1,600 cd/m2.
- Yang, Chiun-Jen,Lee, Jian Haur,Chen, Chin-Ti
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Read Online
- Synthesis of new Zn (II) complexes for photo decomposition of organic dye pollutants, industrial wastewater and photo-oxidation of methyl arenes under visible-light
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Synthesis of new Schiff's base Zn-complexes for photo-oxidation of methyl arenes and xylenes are reported under visible light irradiation conditions. All the synthesized new ligands and Zn-complexes are thoroughly characterized with various spectral analyses and confirmed as 1:1 ratio of Zn and ligand with distorted octahedral structure. The bandgap energies of the ligands are higher than its Zn-complexes. These synthesized new Zn(II) complexes are used for the photo-fragmentation of organic dye pollutants, photodegradation of food industrial wastewater and oxidation of methyl arenes which are converted into its respective aldehydes with moderate yields under visible light irradiation. The photooxidation reaction dependency on the intensity of the visible light was also studied. With the increase in the dosage of photocatalyst, the methyl groups are oxidized to get aldehydes and mono acid products, which are also identified from LC-MS data. Finally, [Zn(PPMHT)Cl] is with better efficiency than [Zn(PTHMT)Cl] and [Zn(MIMHPT)Cl] for oxidation of methyl arenes is reported under visible-light-driven conditions.
- Ahemed, Jakeer,Bhongiri, Yadagiri,Chetti, Prabhakar,Gade, Ramesh,Kore, Ranjith,Pasha, Jakeer,Pola, Someshwar,Rao D, Venkateshwar
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- Meso-substituted boron-dipyrromethene compounds: synthesis, tunable solid-state emission, and application in blue-driven LEDs
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In this work, we depict the synthesis and characterization of a series of meso-substituted boron-dipyrromethene (BODIPY) compounds. Their optical and electrochemical properties were investigated systematically. All these compounds exhibited intense absorption bands in the ultraviolet (UV) and visible regions, which arise from the π–π* transitions based on their BODIPY core segments. By comparing electron-withdrawing substituents and electron-donating substituents, we found that these compounds exhibited some similar photophysical properties but exhibited different fluorescence in the solid state. All compounds were highly emissive in dichloromethane at room temperature (λem = 512–523 nm, ΦPL > 0.9). When these compounds were applied in blue-driven light-emitting diodes (LEDs) as light-emitting materials, the devices showed luminescence efficiency ranging from 1.09 to 34.13 lm/W. Their luminescence and electrochemical properties could be used for understanding the structure–property relationship of BODIPY compounds and developing functional fluorescent materials.
- Liu, Hao,Su, Huan,Chen, Zhiyuan,Zhu, Senqiang,Liu, Rui,Zhu, Hongjun
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p. 1697 - 1705
(2021/07/10)
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- Stable and efficient phosphorescent organic light-emitting device utilizing a δ-carboline-containing host displaying thermally activated delayed fluorescence
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Materials displaying thermally activated delayed fluorescence (TADF) can when used as hosts alleviate the serious efficiency roll-off of phosphorescent organic light-emitting devices (PHOLEDs). However, the stability of the device remains challenging due to the unstable moiety in the TADF molecule. Here, a stable and efficient yellow PHOLED based on a δ-carboline-containing TADF host and bis(4-phenyl-thieno[3,2-c]pyridinato-C2′) (acetylacetonato) iridium(iii) (PO-01) guest was demonstrated. Compared to the lifetime of the PHOLED with a 4,4′-bis(N-carbazolyl)-2,2′-biphenyl host, a greater than twenty times enhancement of the lifetime of the PO-01-based device was achieved. The LT50 lifetime (time to 50% of initial luminance of 1000 cd m-2) of an unpackaged DCb-BPP-based PHOLED reached 424 h, and was accompanied by a maximum external quantum efficiency of 21.5% and an impressive low efficiency roll-off of 17.7% at a high luminance of 10 000 cd m-2. These values are among the best of those reported for PO-01-based yellow PHOLEDs.
- Liu, Shihao,Wang, Hui,Xie, Wenfa,Zang, Chunxiu,Zhang, Letian,Zhao, Hongyu
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p. 3800 - 3806
(2020/03/31)
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- A Protocol to Transform Sulfones into Nitrones and Aldehydes
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A simple method to transform sulfones into nitrones and therefore into the corresponding carbonyl derivatives has been developed. Some examples demonstrate that it is a new reliable and versatile reaction in the toolbox of sulfones that has great synthetic potential. NMR and computational studies were used to elucidate the mechanism.
- Rodrigo, Eduardo,Alonso, Inés,Cid, M. Belén
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supporting information
(2018/09/27)
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- A Protocol to Transform Sulfones into Nitrones and Aldehydes
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A simple method to transform sulfones into nitrones and therefore into the corresponding carbonyl derivatives has been developed. Some examples demonstrate that it is a new reliable and versatile reaction in the toolbox of sulfones that has great synthetic potential. NMR and computational studies were used to elucidate the mechanism.
- Rodrigo, Eduardo,Alonso, Inés,Cid, M. Belén
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supporting information
p. 5789 - 5793
(2018/09/29)
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- Preparation and application of organic thermally induced delayed fluorescence material containing 9,9-dimethyl acridine unit
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The invention belongs to the field of organic luminescent materials, and provides preparation and application of an organic thermally induced delayed fluorescence material containing a 9,9-dimethyl acridine unit. Isophthalonitrile with high eletrophilicity is taken as the electron acceptor, a cyano group with a strong electron-withdrawing performance is introduced, 9,9-dimethyl acridine is taken as the electron donor, and a meta-position connection mode is adopted to obtain the organic micromolecular thermally induced delayed fluorescence material with an excellent luminescence property, and the conventional para-position connection mode is broken through. The organic thermally induced delayed fluorescence material, which contains a 9,9-dimethyl acridine unit and adopts a meta-position connection mode, can be applied to vapor deposition of devices. Meanwhile, the organic thermally induced delayed fluorescence material has the advantages of high yield, high thermal stability, and easy film forming, can be massively produced and used in a large scale, and can be applied to electroluminescent devices to obtain a high efficient electroluminescent performance.
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- Synthesis of Aldehydes by Organocatalytic Formylation Reactions of Boronic Acids with Glyoxylic Acid
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Reported herein is a conceptually novel organocatalytic strategy for the formylation of boronic acids. New reactivity is engineered into the α-amino-acid-forming Petasis reaction occurring between aryl boronic acids, amines, and glyoxylic acids to prepare aldehydes. The operational simplicity of the process and its ability to generate structurally diverse and valued aryl, heteroaryl, and α,β-unsaturated aldehydes containing a wide array of functional groups, demonstrates the practical utility of the new synthetic strategy.
- Huang, He,Yu, Chenguang,Li, Xiangmin,Zhang, Yongqiang,Zhang, Yueteng,Chen, Xiaobei,Mariano, Patrick S.,Xie, Hexin,Wang, Wei
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supporting information
p. 8201 - 8205
(2017/06/30)
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- Polyoxometalate built-in conjugated microporous polymers for visible-light heterogeneous photocatalysis
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Herein, we report two novel Anderson-type polyoxometalate (POM) built-in conjugated microporous polymers (CMPs), Bn-Anderson-CMP and Th-Anderson-CMP prepared through Sonogashira-Hagihara cross-coupling of tetrabromo-bifunctionalized Anderson-type POMs and 1,3,5-triethynylbenzene. These two Anderson-CMPs exhibit outstanding heterogeneous photocatalytic activities towards degrading organic dyes in water. Control photocatalysis experiments with different radical scavengers demonstrate that hydrogen peroxide and singlet oxygen are the primary active catalytic species. Moreover, these two CMPs can be easily recycled at least five times without a noticeable decrease in photocatalytic performances.
- Li, Yusen,Liu, Mingxuan,Chen, Long
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supporting information
p. 13757 - 13762
(2017/07/12)
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- Preparation method of 3,5-dibromo benzaldehyde
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The invention relates to a preparation method of 3,5-dibromo benzaldehyde. The preparation method of the 3,5-dibromo benzaldehyde includes the following steps that tetrahydrofuran, magnesium sheets and 1,3,5-tribromobenzene are stirred to obtain a first mixture; the first mixture is cooled, then a catalyst is added, heating is performed for reflux, the 1,3,5-tribromobenzene is added in batches after triggering, and then heating is performed for reflux and heat preservation so as to obtain a second mixture; after the second mixture is cooled, a solvent is added, then heating is performed for heat preservation so as to obtain a third mixture; the third mixture is acidized, temperature control is performed, and then extraction, concentration, crystallization and centrifugal drying are performed to obtain the 3,5-dibromo benzaldehyde. The formaldehyde content of the 3,5-dibromo benzaldehyde prepared by adopting the method is 99%, and the yield is above 90%.
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Paragraph 0023
(2017/05/27)
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- Novel 9,9′-(1,3-phenylene)bis-9H-carbazole-containing copolymers as hole-transporting and host materials for blue phosphorescent polymer light-emitting diodes
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Novel photo-crosslinkable hole-transport and host materials incorporated into multilayer blue phosphorescent polymer light-emitting diodes (Ph-PLEDs) were demonstrated in this study. The oxetane-containing copolymers, which function as hole-transport layers (HTL), could be cured by UV irradiation in the presence of a cationic photoinitiator. The composition of the two monomers was varied to yield three different hole-transporting copolymers, [Poly(9,9′-(5-(((4-(7-(4-(((3-methyloxetan-3-yl)methoxy)methyl)phenyl) octan-3-yl)benzyl)oxy)methyl)-1,3-phenylene)bis(9H-carbazole)) (P(mCP-Ox)-I, -II, and -III)]. In addition, monomer 1 was copolymerized with styrene to produce copolymer P(mCP-Ph) as a host material for bis[2-(4,6-difluorophenyl) pyridinato-C2,N](picolinato)iridium(III) (FIrpic), a blue-emitting dopant. All mCP-based copolymers displayed high glass transition temperatures (Tg) of up to 130-140 °C and triplet energies of up to 3.00 eV. The blue Ph-PLEDs exhibited a maximum external quantum efficiency of 2.55%, in addition to a luminous efficiency of 8.75 cd A-1 when using the device configuration of indium tin oxide/poly(3,4-ethylenedioxythiophene): poly(styrene sulfonate)/P(mCP-OX)-III/P(mCP-Ph):FIrpic(15 wt %)/3,3′-[5′-[3-(3-pyridinyl)phenyl][1,1′:3′, 1′′-terphenyl]-3,3′′-diyl]bispyridine/LiF/Al. The device bearing P(mCP-Ox)-III HTL, containing the highest composition of mCP unit, exhibited better performance than the other devices, which is attributed to induction of more balanced charge carriers and carrier recombination in the emissive layer. Copyright
- Yoon, Seung Hee,Shin, Jicheol,Um, Hyun Ah,Lee, Tae Wan,Cho, Min Ju,Kim, Yong Jae,Son, Young Hoon,Yang, Joong Hwan,Chae, Geesung,Kwon, Jang Hyuk,Choi, Dong Hoon
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p. 707 - 718
(2014/02/14)
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- Synthesis and characterization of conjugated Dawson-type polyoxometalate-porphyrin copolymers
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Hybrid polyoxometalate-porphyrin copolymeric films were obtained by the electro-oxidation of zinc octaethylporphyrin (ZnOEP) in the presence of a Dawson type polyoxophosphovanadotungstate bearing two pyridyl groups (POM(py) 2). The synthesis of a series of POM(py)2 consisting of [P2W15V3O62]9- functionalized with diol-amide or triol moieties, as well as the characterization of the copolymers are presented.
- Azcarate, Iban,Ahmed, Iftikhar,Farha, Rana,Goldmann, Michel,Wang, Xiaoxia,Xu, Hualong,Hasenknopf, Bernold,Lac?te, Emmanuel.,Ruhlmann, Laurent
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p. 12688 - 12698
(2013/09/02)
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- Nanoporous polyporphyrin as adsorbent for hydrogen storage
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Novel polyporphyrins with high surface area over 1500 m2/g have been synthesized, and their hydrogen absorption capacities were measured. Porphyrin functionalized with thiophenyl groups was designed as starting monomer; the porphyrin cores offer coordination sites for metal ions which could potentially enhance the interaction with hydrogen for favorable hydrogen storage while the thiophenyl groups are used for cross-linking the monomers under oxidative coupling conditions to yield highly porous networks. These polyporphyrins adsorb up to 5.0 mass % H2 at 77 K and 65 bar. Compared with metal free polymer, iron(II)-containing polymer shows finite increase in heat of adsorption for hydrogen, suggesting a promising approach for designing high heat of adsorption porous materials.
- Xia, Jiangbin,Yuan, Shengwen,Wang, Zhuo,Kirklin, Scott,Dorney, Brian,Liu, Di-Jia,Yu, Luping
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experimental part
p. 3325 - 3330
(2011/10/18)
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- Synthesis, characterization, spectroscopy, electronic and redox properties of a new nickel dithiolene system
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A new dithiolene ligand with 3,5-dibromo substituted phenyl groups was designed and synthesized. The protected form of the ligand was reacted with a nickel salt providing neutral Ni(S2C2(3,5-C 6H3Br2)2)2 and anionic [Ni(S2C2(3,5-C6H3Br 2)2)2]- isolated as a Bu 4N+ salt. Both were characterized by UV-Vis and IR spectroscopy and compared with the similar known molecular systems. They exhibit intense low energy transitions that are characteristic of such systems. The electrochemical behavior of these molecules was investigated by cyclic voltammetry.
- Basu, Partha,Nigam, Archana,Mogesa, Benjamin,Denti, Suzanne,Nemykin, Victor N.
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scheme or table
p. 2857 - 2864
(2011/02/28)
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- Luminescent dendrons with oligo(phenylenevinylene) core branches and oligo(ethylene oxide) terminal chains
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Farication of novel amphiphilic light-emitting dendrons with oligo(phenylenevinylene) core branches and oligo(ethylene oxide) terminal chains (OPV-d-OEO) was presented. It was observed that dendrons possess CAC values of 1.60 and ).40 mg/mL, respectively. It was found that the amphiphilic characteristics and resultant aggregation behaviors led to concentration and solvent polarity-dependent fluorescence in solutions. The results show that the solution photoluminescence (PL) spectra for these dendrons display red shifts with increasing concentration and/or solvent polarity.
- Ding, Liming,Chang, Dongwook,Dai, Liming,Ji, Tao,Li, Sinan,Lu, Jianping,Tao, Ye,Delozier, Donavon,Connell, John
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p. 9389 - 9392
(2008/02/01)
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- Synthesis of Anthropomorphic Molecules: The NanoPutians
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Described here are the synthetic details en route to an array of 2-nm-tall anthropomorphic molecules in monomeric, dimeric, and polymeric form. These anthropomorphic figures are called, as a class, NanoPutians. Using tools of chemical synthesis, the ultimate in designed miniaturization can be attained while preparing the most widely recognized structures: those that resemble humans.
- Chanteau, Stephanie H.,Tour, James M.
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p. 8750 - 8766
(2007/10/03)
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- Guest binding and orientation within open nanoscale hosts
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The synthesis of three different nanoscale molecular hosts is reported. These cavitands each possess a highly preorganized cavity with an open portal (nearly 1 nm wide), by which guests can enter and egress the cavity. Additionally, these hosts are deep-functionalized with a crown of weakly acidic benzal C-H groups which can form a variety of noncovalent interactions with guest molecules residing within the cavity. Thirty-one guests were examined for their propensity to form complexes with the hosts. Guests that possess halogen atoms were the strongest binders, suggesting the formation of polydentate C-H···X-R hydrogen bonds with the deep crown of benzal hydrogens. Exchange rates between the free and bound states were noted to be dependent on the size of the guest and the solvent used to study complexation. In general, stronger binding and slower exchange were noted for complexations carried out in DMSO with highly complementary guests. The orientation of each guest within the cavity was determined using either EXSY NMR spectroscopy or 1H NMR shift data, Cumulatively these results showed that the principal factors directing orientation were interactions with the benzal groups and the type of solvent. Van't Hoff analyses of selected complexations were also carried out. As well as revealing that all complexations were entropically unfavorable, these experiments provided support for guest orientation determinations, and gave an estimation that the formation of a C-H···I-R hydrogen bond releases between 1 and 1.5 kcalmol-1.
- Laughrey, Zachary R.,Gibb, Corinne L. D.,Senechal, Tangi,Gibb, Bruce C.
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p. 130 - 139
(2007/10/03)
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- An improved sonogashira coupling procedure for the construction of rigid aromatic multifunctional monomers bearing 1,3-substituted acetylenic units
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The efficient synthesis of rigid multifunctional vinylic monomers 1 and 2 from 3,5-dibromobenzene derivatives and propargyl alcohol via the Sonogashira reaction is reported. For example, a series of 3,5-bis(3-hydroxyprop-1-ynl)benzoate ester derivatives have been prepared efficiently using an improved palladium catalyst system. Subsequent hydrolysis and reaction with 4-vinylaniline afforded a new monomer 2 for use in functional macroporous polymer systems. In addition, Sonogashira and Wittig methodologies have been optimised in order to construct successfully an alternative rigid monomer 1 from 3,5-dibromobenzaldehyde.
- Davidson, Louise,Freebairn, Keith W.,Russell, Andrew T.,Trivedi, Harish S.,Hayes, Wayne
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p. 251 - 254
(2007/10/03)
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- META-GUANIDINE, UREA, THIOUREA OR AZACYCLIC AMINO BENZOIC ACID DERIVATIVES AS INTEGRIN ANTAGONISTS
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The present invention relates to a class of compounds represented by the Formula Ior a pharmaceutically acceptable salt thereof, whereinA ispharmaceutical compositions thereof and methods of using such compounds and compositions as alphavbeta3 antagonists.
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- Synthesis and characterization of stilbene derivatives for possible incorporation as smart additives in polymers used as packaging films
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Several series of stilbene derivatives for possible use as smart additives in polymers used as packaging films have been prepared and characterized. Differential scanning calorimetry was performed on some of the stilbenes in order to determine any liquid crystal properties. Those compounds which had multiple phase transitions were also shown to have two liquid crystalline phases according to optical microscopy.
- Day, Gary M.,Howell, Owen T.,Metzler, Michael R.,Woodgate, Paul D.
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p. 425 - 434
(2007/10/03)
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- 2-(aza-9-fluorenonyl)carbapenem antibacterial agents
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Carbapenems of the formula STR1 wherein a suitably substituted aza-9-fluorenone is attached at the 2-position of the carbapenem are useful antibacterial agents.
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- 2-phenyl-carbapenems
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Carbapenems of the formula STR1 are useful intermediates to antibacterial agents.
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- Synthesis, in Vitro Binding Profile, and Autoradiographic Analysis of -cis-3--2-phenylpiperidine, a Highly Potent and Selective Nonpeptide Substance P Receptor Antagonist Radioligand
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The synthesis of a highly potent and selective NK1 receptor antagonist radioligand, -cis-3--2-phenylpiperidine (6a) is described.The in vitro binding pharmacology and autoradiographic distribution of 6a in guinea pig brain following peripheral administration are also reported.
- Rosen, Terry,Seeger, Thomas F.,McLean, Stafford,Desai, Manoj C.,Guarino, Karen J.,et al.
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p. 3197 - 3201
(2007/10/02)
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- 1,3,5-TRISUBSTITUTED BENZENES I. SYNTHESIS AND REACTIONS OF 3,5-DIBROMOPHENYLLITHIUM
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An improved method for the synthesis of 3,5-dibromophenyllithium (I) has been developed.The reactions between I and various substrates leads to a variety of substituted compounds e.g. (3,5-Br2C6H3)nX; when n = 1, X = -CO2H, -CHO, -Si(CH3)2Cl, -C(O)C3F7, -C(O)CF2(OCF2CF2)3OC2F5, -C(O)CF(CF3)OC3F7, -C(O)CF(CF3)2OC3F7, -C(CF3)2OH and C6F5; when n = 2, X = p-C6F4; when n = 3, X = P.The thermal stability of I is also reported.
- Chen, Loomis S.,Chen, Grace J.,Tamborski, Christ
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p. 281 - 291
(2007/10/02)
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