- Electron-Transfer-Induced Self-Assembly of a Molecular Tweezer Platform
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The design and synthesis of a new molecular tweezer (T-tmp) with electron-rich pincers are reported. The stable monocationic radicals and self-assembled dimeric radicals of this molecular tweezer platform were prepared by chemical oxidative titration. With the aid of DFT calculations, it was found that the dimeric radicals with syn-syn-syn conformer has the most stable structure, with the hole primarily delocalized between parallel stacked pyrenyl groups.
- Thakur, Khushabu,Wang, Denan,Mirzaei, Saber,Rathore, Rajendra
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- Conversion of Imine to Oxazole and Thiazole Linkages in Covalent Organic Frameworks
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Imine-linked ILCOF-1 based on 1,4-phenylenediamine and 1,3,6,8-tetrakis(4-formylphenyl)pyrene was converted through consecutive linker substitution and oxidative cyclization to two isostructural covalent organic frameworks (COFs), having thiazole and oxazole linkages. The completeness of the conversion was assessed by infrared and solid-state NMR spectroscopies, and the crystallinity of the COFs was confirmed by powder X-ray diffraction. Furthermore, the azole-linked COFs remain porous, as shown by nitrogen sorption experiments. The materials derived in this way demonstrate increased chemical stability, relative to the imine-linked starting material. This constitutes a facile method for accessing COFs and linkages that are otherwise difficult to crystallize due to their inherently limited microscopic reversibility.
- Waller, Peter J.,Alfaraj, Yasmeen S.,Diercks, Christian S.,Jarenwattananon, Nanette N.,Yaghi, Omar M.
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- Mono- and Diruthenium, Symmetrical and Unsymmetrical Complexes Bridged by Pyrene Derivatives: Experimental and Theoretical Studies
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New mono- and diruthenium, symmetrical and unsymmetrical complexes, bridged by a new cyclometalating 1,3,6,8-tetra(4-substituted-2-pyridyl)pyrene derivative containing the solubilizing group 2,2-dimethylpropyloxy, with the terminal 4′-phenyl-2,2′:6′,2′′-terpyridine ligands containing diethylamine and a 2-ethynyl-9,9-dioctylfluorene moiety, were synthesized and thoroughly characterized. Thermal studies show that the obtained complexes retain high thermal stability. Spectroscopic studies show the metal-to-ligand charge-transfer excitation. Further, electrochemical studies show delocalization of the electronic charge (mixed valance). In addition, density functional theory and time-dependent density functional theory calculations have provided more detail about the structural properties and a deeper understanding of the experimental results. All of the obtained results show the considerable differences between the mono- and diruthenium and symmetrical and unsymmetrical complexes.
- Zych, Dawid,Slodek, Aneta,Paj?k, Micha?,Krompiec, Stanis?aw,Spólnik, Grzegorz,Danikiewicz, Witold
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- A lanthanide-organic crystalline framework material encapsulating 1,3,6,8-tetrakis(: P -benzoic acid)pyrene: Selective sensing of Fe3+, Cr2O72- and colchicine and white-light emission
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A facile strategy was used to construct a series of composite materials with color-tunable and white light emission by encapsulating 1,3,6,8-tetrakis(p-benzoic acid)pyrene (H4TBAPy) into framework material [Eu(MCTCA)1.5(H2O)2]·1.75H2O (Eu-MCTCA), which is synthesized based on Eu(NO3)3·6H2O and 5-methyl-1-(4-carboxylphenyl)-1H-1,2,3-triazole-4-carboxylic acid (H2MCTCA). A slight adjustment of the emission color can be easily fulfilled by simply altering the concentration of H4TBAPy or regulating the excitation wavelength. Notably, white light emitting Eu-MCTCA@H4TBAPy can be realized by encapsulating H4TBAPy with a concentration of 0.75 mM, when the excitation wavelength is 350 nm. Furthermore, based on the favorable luminescence and stable structure of Eu-MCTCA@H4TBAPy in water or organic solvents, Eu-MCTCA@H4TBAPy can be used as a potential luminescent probe for detecting Fe3+, Cr2O72- and colchicine.
- Li, Jin Xiao,Guan, Qing Lin,Wang, Yu,You, Zi Xin,Xing, Yong Heng,Bai, Feng Ying,Sun, Li Xian
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- Tailoring the framework of organic small molecule semiconductors towards high-performance thermoelectric composites: Via conglutinated carbon nanotube webs
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Recently, the thermoelectric (TE) properties of single-walled carbon nanotubes (SWCNTs)/polymer semiconductor composites have been dramatically improved; however, there are no examples of SWCNTs/organic small molecule semiconductor (OSMS) composites as TE materials, although OSMSs are more attractive due to their exact structure, easy structure optimization, high purity for performance optimization, etc. In this work, four p-type OSMSs are designed and synthesized as p-type binders for application in SWCNT-doped composite films. The relationship between TE properties and the structure including the conjugated-backbone and peripheral substituents is investigated. Photophysical spectroscopic and scanning electron microscopic studies indicate that the variation of molecular geometries and hybrid ratios results in obvious changes in the morphologies, interfacial contacts and grain boundaries of the composite films, subsequently affecting the TE properties of the samples. Notably, the SWCNT/TCzPy (1:1)-based hybrid film exhibits the best performance with an average power factor of 108.4 ± 4.8 μW m-1 K-2, which is three times higher than that of SWCNT/TDOPAPy. The results demonstrate that fine tuning the π-extensions of the central core or peripheral substituents of organic semiconductors is a good strategy for designing high-performance p-type organic small molecule TE materials.
- Yin, Xiaojun,Peng, Yuhao,Luo, Jiajia,Zhou, Xiaoyan,Gao, Chunmei,Wang, Lei,Yang, Chuluo
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- A unique magnesium-based 3D MOF with nanoscale cages and temperature dependent selective gas sorption properties
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A porous Mg-based 3D metal-organic framework with unique nanoscale cages and two-fold interpenetrating pcu nets has been synthesized and characterized. It shows gas-uptake capacities for N2, H2, O2 and CO2 at low temperatures and selective adsorption of CO 2 over O2 and N2 at room temperature. The Royal Society of Chemistry 2013.
- Huang, Yong-Liang,Gong, Yun-Nan,Jiang, Long,Lu, Tong-Bu
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- Furyl derivatives of pyrene: Efficient synthesis and relevant optical properties
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A series of various furyl derivatives of pyrene were synthesized by Stille cross-coupling procedure. Their structures were characterized by nuclear magnetic resonance, and elemental analysis. Optical properties of the synthesized materials as well as their energy levels were investigated by ultraviolet-visible absorption supported by fluorescence spectra. All of the studied compounds exhibit fluorescence with energy peaks dependent on the number of furyl substituents. Furthermore, quantum mechanical modeling method of obtained materials are studied. Experimental data are focused on quantum chemical calculations. Highest occupied molecular and lowest unoccupied molecular orbitals are delocalized uniformly on both pyrene core and furyl substituents. Furanyl-pyrene hybrids are potentially good materials for optical applications mainly due to their optical and charge transport properties, which are also desired for electronic applications.
- Idzik, Krzysztof R.,Ledwon, Przemyslaw,Licha, Tobias,Kuznik, Wojciech,Lapkowski, Mieczyslaw,Frydel, Jaroslaw
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- Synthesis of pyrene-cored dendrimers with 9-phenylcarbazole-based dendrons and their thermal, photophysical and electrochemical properties
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Three generations of dendrimers (G1, G2 and G3) with a pyrene core and 9-phenylcarbazole derivatives dendrons have been designed and synthesized by convergent approach. Their chemical structures were well characterized by means of 1H NMR, IR spectroscopy, MALDI-TOF MS and elemental analysis. The studies revealed interesting effects of topological variation with incremental generation number on the thermal, photophysical and electrochemical properties of the dendrimers. The results showed that they displayed excellent thermal stability with 5% weight-loss temperature up to 610 °C and high glass-transition temperature (260 °C for G3). The HOMO and energy band gaps of materials could be modulated by changing the generation of the dendrimers. Compared to G1 and G2, the higher generation G3 had significantly enhanced photoluminescent quantum yield from 86.9 to 99.5%, and exhibited good stability for hole and electron injection.
- You, Jia,Li, Guiyang,Wang, Zhonggang
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- Synthesis and fluorescence emission properties of 1,3,6,8-tetrakis(9H- fluoren-2-yl)pyrene derivative
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A novel pyrene-based highly pure blue fluorescent and stable molecule, 1,3,6,8-tetrakis[9,9-bis(3-methylbutyl)-9Hfluoren- 2-yl]pyrene, was successfully synthesised via a Pd-catalysed Suzuki coupling reaction of 1,3,6,8- tetrabromopyrene with 2-[9,9-bis(3-methylbutyl)-9H-fluoren-2-yl]-4,4,5,5- tetramethyl[1,3,2]dioxaborolane. The photoproperties of this pyrene were examined in detail and these data indicated its potential application as blue-emitting materials in organic light-emitting diodes.
- Hu, Jian-Yong,Hiyoshi, Hidetaka,Do, Jung-Hee,Yamato, Takehiko
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- Ultrastable conductive microporous covalent triazine frameworks based on pyrene moieties provide high-performance CO2 uptake and supercapacitance
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Covalent organic triazine frameworks (CTFs) are a subclass of covalent organic frameworks and conjugated microporous polymers that exhibit heteroatom effects and possess high surface areas and excellent chemical and thermal stabilities; they have applications in energy storage and gas adsorption. In this study, we prepared two microporous polymers the pyrene-functionalized CTFs Pyrene-CTF-10 and Pyrene-CTF-20 - through ionothermal treatment of 1,3,6,8-cyanopyrene (TCNPy) in the presence of molten zinc chloride (ZnCl2) at 500 °C (at ZnCl2-to-TCNPy molar ratios of 10?:?1 and 20?:?1, respectively). Pyrene-CTF-10 and Pyrene-CTF-20 had specific BET surface areas of 819 and 1019 m2 g-1, respectively, with pore size distributions of 1.10 and 1.35 nm, respectively, and high char yields (up to 70%). Furthermore, these Pyrene-CTF polymeric frameworks exhibited excellent specific capacitances at a current density of 0.5 A g-1: 380 F g-1 for Pyrene-CTF-10 and 500 F g-1 for Pyrene-CTF-20. In addition, both Pyrene-CTFs had excellent cycling stability, retaining 97% of their capacitances after cycling 2000 times at a current density of 10 A g-1. Moreover, Pyrene-CTF-10 displayed good CO2 uptake capacity (2.82 and 5.10 mmol g-1 at 298 and 273 K, respectively).
- Mohamed, Mohamed Gamal,El-Mahdy, Ahmed F. M.,Takashi, Yasuno,Kuo, Shiao-Wei
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- Ethynylpyrene Linked Benzocrown Ethers as Fluorescent Sensors for Metal Ions
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Substances containing ethynylpyrenes linked to either one or four benzocrown ethers were synthesized, and their absorption and fluorescence spectroscopic responses to metal ions were assessed. Addition of metal perchlorates to solutions of these substances promotes short wavelength shifts in their absorption and fluorescence maxima and increases in their fluorescence intensities. The magnitudes of the fluorescence intensity increases are dependent on the ring size and number of the crown ether and the nature of the metal cation. Association constants for complex formation were calculated using fluorescence intensity versus concentration data. Analysis using Job's plots showed that the substances containing one benzocrown ether moiety form 1:1 complexes with metal ions. Results of experiments employing repeated addition and removal of Mg(ClO4)2 demonstrate that the ON-OFF fluorescence response can be repeated at least three times. Results of molecular orbital calculations show that complexation with metal ions lowers the energies of both the π and π* levels of the ethynylpyrene moiety and that in some cases the vacant orbital on the metal becomes the LUMO of the complex. An explanation of the spectroscopic changes promoted by metal ions is proposed in terms of electrostatic repulsion and structural regulation.
- Maeda, Hajime,Tanaka, Kazuhiro,Aratani, Mona,Segi, Masahito
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- Fast detection of nitroaromatics using phosphonate pyrene motifs as dual chemosensors
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A new class of dual fluorescent chemosensors for nitroaromatic compounds (NACs) based on phosphonated pyrene derivatives is reported, showing high selectivity towards trinitrotoluene (TNT). The strong intermolecular interactions (π-π stacking and hydrogen bonding) allow high fluorescence quenching with visual detection in short response times. This journal is the Partner Organisations 2014.
- Venkatramaiah,Firmino, Ana D. G.,Almeida Paz, Filipe A.,Tomé, Jo?o P. C.
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- Substituent effect of conjugated microporous polymers on the photocatalytic hydrogen evolution activity
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The construction of a donor-acceptor (D-A) organic photocatalyst is a facile approach to improve photocatalytic performances because of the efficient separation of light-generated electrons and holes. The rational design of molecular skeletons and the selection of functional groups are of great importance to an organic photocatalyst with a high photocatalytic activity. Herein, we designed two D-A conjugated microporous polymers (CMPs) with different substituent groups of fluorine atoms and methyl groups on the acceptor unit of dibenzothiophene-dioxide (DBTDO). This study reveals that the introduction of fluorine atoms with strong electron-withdrawing ability onto the acceptor unit can further enhance the electron acceptability of the DBTDO unit, leading to the efficient separation of light-generated electrons and holes, while the introduction of methyl with electron-pushing ability decreases the electron acceptability of the acceptor unit, suppressing the separation of light-generated charge carriers. As a result, the polymer PyDF with fluorine atoms shows an excellent photocatalytic activity compared to PyDM with methyl groups. Under UV/Vis light irradiation, PyDF shows an attractive photocatalytic hydrogen generation rate of 18.93 mmol h-1 g-1, which is much higher than that of PyDM (3.96 mmol h-1 g-1), implying that the functional group acts as a vital role in the catalytic activity of polymer semiconducting photocatalysts.
- Chen, Yu,Gao, Xiaomin,Jiang, Jia-Xing,Ma, Wenyan,Ren, Shi-Bin,Shu, Chang,Wang, Feng,Zeng, Jing Hui,Zhang, Chong
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- Trimethylsilyl Group Assisted Stimuli Response: Self-Assembly of 1,3,6,8-Tetrakis((trimethysilyl)ethynyl)pyrene
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Substitution of 1,3,6,8-tetraethynylpyrene with sterically bulky trimethylsilyl groups enabled four modes of molecular packing, two polymorphs (triclinic system (Y-form) and "loose" crystal Colho (OK-form)), a "rigid" liquid crystalline phase Colho (OC-form), and an amorphous phase (OA-form), which emitted fluorescence at different wavelengths under UV light. The four phases could be interconverted by physical stimuli such as heating, grinding by mortar and pestle, and exposing to the vapor of organic solvents.
- Xu, Feng,Nishida, Takanori,Shinohara, Kenta,Peng, Lifen,Takezaki, Makoto,Kamada, Takahiro,Akashi, Haruo,Nakamura, Hiromu,Sugiyama, Kouki,Ohta, Kazuchika,Orita, Akihiro,Otera, Junzo
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- Two Li-Zn cluster-based metal-organic frameworks: Strong H2/CO2 binding and high selectivity to CO2
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Two metal-organic frameworks (MOFs) {(Me2NH2)[ZnLi(PTCA)(H2O)]}nn{3DMFC4H8O2 4H2O} (1) and {(Me2NH2)[ZnLi(PTCA)]}nn{3DMF 5H2O} (2) have been constructed from Li-Zn clusters and pyrene-1,3,6,8-tetracarboxylic acid (H4PTCA) under solvothermal conditions. Gas sorption measurements have revealed that the pore of desolvated 2 (2d) can strongly interact with H2 and CO2, with high H2 and CO2 adsorption heats of 15.3 and 51.9 kJ/mol, respectively. Furthermore, 2d can selectively adsorb CO2 over N2and CH4, with high adsorption selectivity of CO2/N2 and CO2/CH4.
- Huang, Yong-Liang,Zhong, Di-Chang,Jiang, Long,Gong, Yun-Nan,Lu, Tong-Bu
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- Design and synthesis of efficient electrogenerated chemiluminescent emitters derived from pyrene
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The design and synthesis of novel dendrimeric structures derived from a pyrene core with substituted triphenylamine and carbazole periphery demonstrated how molecular engineering allowed the fine tuning of the electrogenerated chemiluminiscence (ECL) properties. These two compound (Py-CBZ and Py-TPA) in comparison with the parent structures (Py and Py-Core) showed better chemical stability and anti-aggregation capability. At the same time, the photophysical (Absλmax, E00FLλmaxΦFL), photochemical (oxygen quenching), electrochemical (redox potentials) and optoelectronic (HOMO-LUMO gap and their energy position) properties were modulated, resulting in obtaining two highly ECL emitting molecular structures (Py-CBZ and Py-TPA). This study showed that functionalization of organic dyes with redox moieties (with the proper linker and position) improved the radical stability and also, modulated the optoelectronic properties with the concomitant enhancement of the ECL performance and their potential use in applications such as organic light-emitting devices.
- Cappellari, Maria V.,Mangione, María I.,Spanevello, Rolando A.,Marzari, Gabriela,Morales, Gustavo M.,Fungo, Fernando
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- Effects of substituents on silicon atoms upon absorption and fluorescence properties of 1,3,6,8-tetrakis(silylethynyl)pyrenes
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Synthesis, UV–vis absorption, and fluorescence spectroscopic properties of 1,3,6,8-tetrakis(silylethynyl)pyrenes 2–10 were studied. Absorption maxima of CH2Cl2 solutions of these compounds appeared at 437–445 nm, and molar absorption coefficients (ε) of most of these compounds exceeded 105 L mol?1 cm?1. Fluorescence emissions measured in dilute CH2Cl2 solutions are observed in visible region, and their intensities remarkably increased compared with that of pyrene. Fluorescence spectra obtained from concentrated CH2Cl2 solutions exhibited broad excimer emissions when steric bulk of substituents on silicon atoms is sufficiently low. Molecular orbital calculations indicated that HOMO-LUMO energy gap decreased with increasing the number of phenyl groups on silicon atoms, and that the silyl groups act as electron-donating groups to tetraethynylpyrene core. Resonances in 29Si NMR spectra shifts to upfield with increasing the number of phenyl groups on silicon atoms due to the shielding effect of phenyl groups.
- Maeda, Hajime,Shoji, Tomokazu,Segi, Masahito
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- Pyrene-capped starburst emitters as gain media for organic lasers: Design, synthesis, and stabilized lasing properties
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A set of pyrene-capped starburst organic emitters composed of a non-planar cross-shaped spirofluorene core (SF-PyF) and a large rigid planar pyrene core (Py-PyF) have been designed, synthesized and explored as efficient emitters for organic lasers. High photoluminescence yields and excellent thermal stability of SF-PyF and Py-PyF in neat films make them promising optical gain media. Low amplified spontaneous emission (ASE) thresholds of 6.6 μJ cm-2 (1.3 kW cm-2) at 451 nm for SF-PyF and 5.4 μJ cm-2 (1.1 kW cm-2) at 490 nm for Py-PyF were obtained (pump pulse: λp = 355 nm, 10 Hz, 5 ns). Distributed feedback (DFB) lasers based on SF-PyF and Py-PyF exhibited good performance with low thresholds (16 nJ per pulse for SF-PyF and 24 nJ per pulse for Py-PyF, respectively) and the full width at half maximum of about 0.2 nm. Surprisingly, DFB lasers integrated with SF-PyF and Py-PyF as gain media exhibited excellent ambient photostability and superior reliability even in hot water (80 °C). The excellent stability of ASE spectra, electroluminescence spectra and lasing spectra under harsh conditions manifests that the resulting pyrene-capped starburst emitters are beneficial for improving the lasing stability issues. The study sheds light on exploring robust organic gain media toward electrically pumped OSLs.
- Yi, Jian-Peng,Zhao, Li,Xu, Weidong,Liu, Cheng-Fang,Lai, Wen-Yong,Huang, Wei
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- Synthesis, absorption, and fluorescence-emission properties of 1,3,6,8-tetraethynylpyrene and its derivatives
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The synthesis of several 1,3,6,8-tetraethynylpyrene derivatives is reported. The effect of extended acetylenic conjugation on their absorption and fluorescence-emission properties is studied. Significant bathochromic shifts of both the absorption and fluorescence emission bands are observed. These derivatives emit fluorescence in the visible (400-550 nm) region. Wiley-VCH Verlag GmbH & Co. KGaA, 2005.
- Venkataramana, Gandikota,Sankararaman, Sethuraman
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- A tetraalkylated pyrene building block for the synthesis of pyrene-fused azaacenes with enhanced solubility
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The synthesis and characterisation of a soluble pyrene-fused tetraazaoctacene derivative has been achieved by developing a key pyrene-based building block with four solubilising groups.
- Kulisic, Niksa,More, Sandeep,Mateo-Alonso, Aurelio
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- Isolation and X-ray structural characterization of tetraisopropylpyrene cation radical
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A practical synthesis of 1,3,6,8-tetraisopropylpyrene and the isolation and X-ray structural characterization of its monomeric cation radical salt are described. The Royal Society of Chemistry.
- Banerjee, Moloy,Vyas, Vijay S.,Lindeman, Sergey V.,Rathore, Rajendra
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- Ultrastable tetraphenyl-: P -phenylenediamine-based covalent organic frameworks as platforms for high-performance electrochemical supercapacitors
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In this study we synthesized two tetraphenyl-p-phenylenediamine-based covalent organic frameworks (TPPDA-TPPyr and TPPDA-TPTPE COFs) for potential use in high-performance electrochemical supercapacitors. This excellent performance arose from their structures containing redox-active triphenylamine derivatives and their high surface areas.
- El-Mahdy, Ahmed F. M.,Mohamed, Mohamed Gamal,Mansoure, Tharwat Hassan,Yu, Hsiao-Hua,Chen, Tao,Kuo, Shiao-Wei
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- The optical properties and quantum chemical calculations of thienyl and furyl derivatives of pyrene
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A detailed electrochemical, photophysical and theoretical study is presented for various new thienyl and furyl derivatives of pyrene. Their optical properties are described based on UV-VIS absorption and both steady-state and time-resolved fluorescence spectroscopy. DFT and TDDFT calculations are also presented to support experimental data. The calculations results show that HOMO-LUMO orbitals are delocalized uniformly between aromatic core and aryl substituents. Good electrochemical stability of thienyl and furyl hybrids of pyrene confirm their potential application for light emitting electrochemical cells or spintronics mainly due to their beneficial optical and charge transport properties in electrochromic devices. In order to demonstrate this potential, an OLED device is presented. Synthesized compounds included in this OLED device both facilitate electron transport and act as a light emitting layer.
- Idzik, Krzysztof R.,Cywiński, Piotr J.,Kuznik, Wojciech,Frydel, Jaroslaw,Licha, Tobias,Ratajczyk, Tomasz
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- NCN-Coordinating Ligands based on Pyrene Structure with Potential Application in Organic Electronics
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Five novel derivatives of pyrene, substituted at positions 1,3,6,8 with 4-(2,2-dimethylpropyloxy)pyridine (P1), 4-decyloxypyridine (P2), 4-pentylpyridine (P3), 1-decyl-1,2,3-triazole (P4), and 1-benzyl-1,2,3-triazole (P5), are obtained through a Suzuki–Miyaura cross-coupling reaction or CuI-catalyzed 1,3-dipolar cycloaddition reaction, respectively, and characterized thoroughly. TGA measurements reveal the high thermal stability of the compounds. Pyrene derivatives P1–P5 all show photoluminescence (PL) quantum yields (Φ) of approximately 75 % in solution. Solid-state photo- and electroluminescence characteristics of selected compounds as organic light-emitting diodes are tested. In the guest–host configuration, two matrixes, that is, poly(N-vinylcarbazole) (PVK) and a binary matrix consisting of PVK and 2-tert-butylphenyl-5-biphenyl-1,3,4-oxadiazole (PBD) (50:50 wt %), are applied. The diodes show red, green, or blue electroluminescence, depending on both the compound chemical structure and the actual device architecture. In addition, theoretical studies (DFT and TD-DFT) provide a deeper understanding of the experimental results.
- Zych, Dawid,Kurpanik, Aneta,Slodek, Aneta,Maroń, Anna,Paj?k, Micha?,Szafraniec-Gorol, Gra?yna,Matussek, Marek,Krompiec, Stanis?aw,Schab-Balcerzak, Ewa,Kotowicz, Sonia,Siwy, Mariola,Smolarek, Karolina,Ma?kowski, Sebastian,Danikiewicz, Witold
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- Pyrene-containing conjugated organic microporous polymers for photocatalytic hydrogen evolution from water
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Photoactive conjugated microporous polymers (CMPs) are emerging as porous materials capable of mediating the photocatalytic evolution of H2from water. In this study, we synthesized three pyrene-based CMPs (Py-F-CMP, Py-TPA-CMP, Py-TPE-CMP) through Sonogashira-Hagihara cross-couplings of 1,3,6,8-tetraethynylpyrene (Py-T, as a common monomer building block) with 2,7-dibromo-9H-fluorene (F-Br2), tris(4-bromophenyl)amine (TPA-Br3), and 1,1,2,2-tetrakis(4-bromophenyl)ethene (TPE-Br4), respectively, in the presence of Pd(PPh3)4in DMF/Et3N. We then characterized the chemical structures, crystallinities, thermal stabilities, surface morphologies, and porosities of these three new CMPs. Brunauer-Emmett-Teller (BET) analyses and tests of photocatalytic H2production revealed that Py-TPA-CMP displayed the highest BET surface area (454 m2g?1), highest total pore volume (0.28 cm3g?1), highest H2evolution rate (19?200 μmol h?1g?1), and highest apparent quantum yield (15.3%) when compared with those of Py-F-CMP, Py-TPE-CMP, and other organic porous materials.
- Mohamed, Mohamed Gamal,Elsayed, Mohamed Hammad,Elewa, Ahmed M.,EL-Mahdy, Ahmed F. M.,Yang, Cheng-Han,Mohammed, Ahmed A. K.,Chou, Ho-Hsiu,Kuo, Shiao-Wei
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- A guest-responsive fluorescent 3D microporous metal-organic framework derived from a long-lifetime pyrene core
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The carboxylate ligand 1,3,6,8-tetrakls(p-benzolc acld)pyrene (TBAPy)-based on the strongly fluorescent long-lifetime pyrene core-affords a permanently microporous fluorescent metal-organic framework, [In2(OH) 2(TBAPy)] · (guests) (1), displaying 54% total accessible volume and excellent thermal stability. Fluorescence studies reveal that both 1 and TBAPy display strong emission bands at 471 and 529 nm, respectively, upon excitation at 390 nm, with framework coordination of the TBAPy ligands significantly increasing the emission lifetime from 0.089 to 0.110 ms. Upon desolvation, the emission band for the framework Is shifted to lower energy: however, upon re-exposure to DMF the as-made material is regenerated with reversible fluorescence behavior. Together with the lifetime, the emission intensity is strongly enhanced by spatial separation of the optically active ligand molecules within the MOF structure and Is found to be dependent on the amount and chemical nature of the guest species In the pores. The quantum yield of the material Is found to be 6.7% and, coupled with the fluorescence lifetime on the millisecond time scale, begins to approach the values observed for Eu(lll)-cryptate-derlved commercial sensors.
- Stylianou, Kyriakos C.,Heck, Romain,Chong, Samantha Y.,Bacsa, John,Jones, James T.A.,Khimyak, Yaroslav Z.,Bradshaw, Darren,Rosseinsky, Matthew J.
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- Modulation of Gas Sorption Properties through Cation Exchange within an Anionic Metal–Organic Framework
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A novel 3D anionic metal–organic framework (MOF) of (Me2NH2)4[Ni8(PTCA)4(μ3-OH)4(H2O)4](DMF)5(H2O)13 (H4PTCA=pyrene-1,3,6,8-tetracarboxylic acid) has been synthesized, in which Me2NH2 + can be exchanged by Li+ ions. The results of gas sorption measurements indicate that the desolvated MOFs both before and after Li+ exchange show highly selective adsorption for CO2 over CH4 and N2 gases, and the Li+-exchanged MOF exhibits enhanced CO2, CH4, and H2 storage properties.
- Huang, Yong-Liang,Jiang, Long,Lu, Tong-Bu
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- Platform Synthetic Lectins for Divalent Carbohydrate Recognition in Water
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Biomimetic carbohydrate receptors (“synthetic lectins”) have potential as agents for biological research and medicine. However, although effective strategies are available for “all-equatorial” carbohydrates (glucose, etc.), the recognition of other types of saccharide under natural (aqueous) conditions is less well developed. Herein we report a new approach based on a pyrene platform with polar arches extending from aryl substituents. The receptors are compatible with axially substituted carbohydrates, and also feature two identical binding sites, thus mimicking the multivalency observed for natural lectins. A variant with negative charges forms 1:2 host/guest complexes with aminosugars, with K1>3000 m?1for axially substituted mannosamine, whereas a positively charged version binds the important α-sialyl unit with K1≈1300 m?1.
- Carter, Tom S.,Mooibroek, Tiddo J.,Stewart, Patrick F. N.,Crump, Matthew P.,Galan, M. Carmen,Davis, Anthony P.
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- Heteroporous bifluorenylidene-based covalent organic frameworks displaying exceptional dye adsorption behavior and high energy storage
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In this study we performed one-pot polycondensations of BFTB-4CHO with PyTA-4NH2, BFTB-4NH2, and BCTA-4NH2 to prepare the bifluorenylidene-based covalent organic frameworks (COFs) BFTB-PyTA, BFTB-BFTB, and BFTB-BCTA, respectively. These three COFs possessed extremely high thermal stabilities, excellent crystallinities, and high specific surface areas. The BFTB-PyTA COF featured pores of a single size, whereas the BFTB-BFTB and BFTB-BCTA COFs had dual porosities. The COFs were exceptional adsorbers of the small dye molecule rhodamine B (RhB) in water; the maximum adsorption capacities reached as high as 2127 mg g-1, outpacing those of all previously reported COFs, conjugated polymers, activated carbons, and other common nanoporous adsorbents. In addition, our COFs reached up to 99.2% of their maximum adsorption capabilities very rapidly (within 5 min). Furthermore, these COFs displayed good performance when used in electrodes for supercapacitors, with high stability after 2000 cycles. The superior adsorption efficiencies, ultrafast kinetics, and excellent reusability endow such COFs with tremendous potential for use as materials for removing RhB-and, presumably, other organic pollutants-from wastewater.
- Chen, Tao,El-Mahdy, Ahmed F. M.,Kuo, Shiao-Wei,Wang, Hao-Xin,Yamauchi, Yusuke,Zakaria, Mohamed Barakat
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- An Organic Molecular Photocatalyst Releasing Oxygen from Water
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Artificial photosynthesis employing solar energy is one of the best means of reaching a sustainable energy cycle, in which water is oxidized to oxygen and supplies electrons for fuel generation. The development of suitable oxygen evolution materials driven by sunlight is hence the most challenging research topic in the field of photocatalysis. Herein, photocatalytic O2 production from water at a rate of 22.6 μmol h?1 was performed by using a pyrene-based organic molecule constructed through the Ullmann coupling reaction. Its significantly improved light-harvesting ability and notably accelerated separation and transfer of photogenerated charges enhanced the O2 evolution efficiency. This study highlights the structural design of organic molecules applied to photocatalytic water splitting.
- Li, Qinghe,Liu, Feng,Lin, Feng,Lin, Wei,Wang, Xinchen
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Read Online
- Photophysical properties of 1,3,6,8-tetraarylpyrenes and their cation radicals
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The synthesis of 1,3,6,8-tetraaryl substituted pyrenes is described. The substituents on the aryl groups influence the optoelectronic properties of the pyrene core indicating a strong coupling between the aryl groups and the pyrene core. Electronic absroption spectra of the cation radicals generated in solution by the single electron oxidation of pyrenes reaffirmed the coupling of the aryl rings with the pyrene. The aryl groups at 1,3,6,8-positions completely inhibit the π-stacking of pyrene core in solution. Crystal structure of the cation radical salt of tetraphenyl shows charge delocalization between neutral pyrene unit and two cationic pyrene cores. Complete inhibition of the pyrene core stacking is observed in the solid state of cation radical when the dendritic pentaphenyl groups surround the pyrene core.
- Vyas, Vijay S.,Lindeman, Sergey V.,Rathore, Rajendra
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Read Online
- Exploitation of two-dimensional conjugated covalent organic frameworks based on tetraphenylethylene with bicarbazole and pyrene units and applications in perovskite solar cells
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In this work, two-dimensional conjugated covalent organic frameworks (2D-COF) based on a building block of tetraphenylethylene are successfully developed. Bicarbazole and pyrene moieties are respectively coupled with 4,4′,4′′,4′′′-(ethane-1,1,2,2-tetrayl)tetranilino (ETTA)via[4 + 4] solvothermal condensation conditions of 3,3′,6,6′-tetraformyl-9,9′-bicarbazole (Car-4CHO) and 1,3,6,8-tetrakis(4-formylphenyl)pyrene (TFPPy) to affordCar-ETTAandTFPPy-ETTACOFs. According to thermogravimetric analysis (TGA), powder X-ray diffraction (PXRD), and N2adsorption and desorption measurements, bothCar-ETTAandTFPPy-ETTACOFs exhibit excellent thermal stability, highly crystalline structure, and high specific surface area, respectively. These findings are supported by force field andab initiocalculations. Furthermore, successful applications of these COFs in perovskite solar cells (PVSCs) are demonstrated owing to their well-conjugated properties and π-π interactions. While serving as interlayers in the devices, these COFs could effectively promote the interfacial charge dynamic to further optimize the resulting performance. Besides, certain interaction between COFs and perovskite also leads to an improved morphology and crystallinity of the perovskite layer, presenting defect passivation capability. As a result, we show that the performance of the COF-modified PVSC could be improved from 17.40 to 19.80%.
- Chueh, Chu-Chen,EL-Mahdy, Ahmed F. M.,Kuo, Shiao-Wei,Lüder, Johann,Lee, Chia-Chen,Li, Zhen,Mohamed, Mohamed Gamal,Yu, Ming-Hsuan,Zhu, Zonglong
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- Synthesis and optical properties of various thienyl derivatives of pyrene
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A series of various thienyl derivatives of pyrene were synthesized by Stille cross-coupling procedure. Their structures were characterized by 1H NMR, 13C NMR and elemental analysis. The spectroscopic characteristics were investigated by UV-vis absorption and fluorescence spectra. Based on quantum chemical calculations, the energy levels of investigated molecules with respect to the pyrene molecule were also discussed.
- Idzik, Krzysztof R.,Licha, Tobias,Lukes, Vladimir,Rapta, Peter,Frydel, Jaroslaw,Schaffer, Mario,Taeuscher, Eric,Beckert, Rainer,Dunsch, Lothar
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Read Online
- A specific chemodosimeter for fluoride ion based on a pyrene derivative with trimethylsilylethynyl groups
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Pyrene derivative 1 containing four trimethylsilylethynyl substituents was synthesized and investigated as a chromogenic and fluorescent chemodosimeter sensor for fluoride ions. 1 showed a high sensitivity and specific selectivity over a rapid response time toward fluoride anions compared to other anions, such as Cl-, Br-, ClO4-, H 2PO4- and HPO42-. TD-DFT calculations showed that the delocalization of the σ-electrons of the silicon destabilized the HOMO energy level of 1, thus red shifting both its absorption and emission spectrum. The addition of F- removed the trimethylsilyl substituents and resulted in a blue shift of both the absorption and fluorescent spectra of 1, which could be monitored by the color change with the naked-eye. Moreover, an easy to prepare test paper, which was obtained by immersing a filter paper into a THF solution of 1, could be utilized to detect and estimate the concentration of fluoride anions in water.
- Lu, Hua,Wang, Qiuhong,Li, Zhifang,Lai, Guoqiao,Jiang, Jianxiong,Shen, Zhen
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- Cobalt metal organic framework material based on tetra(pyrazolyl)pyrene ligand as well as preparation method and application thereof
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The invention discloses a cobalt metal organic framework material based on tetra(pyrazolyl)pyrene ligand as well as a preparation method and application thereof, belonging to the technical field of crystalline materials. The chemical molecular formula of the material is Co(H4TPP)(CH3COO)2(H2O)(CH3CN)2, wherein H4TPP is an organic ligand, namely 1,3,6,8-tetra(1H-pyrazol-4-yl)pyrene. The preparation method of the metal organic framework comprises the following step: under a closed condition, carrying out a solvothermal reaction on the organic ligand 1,3,6,8-tetra(1H-pyrazol-4-yl)pyrene and cobalt nitrate in a mixed solution of N,N-dimethylformamide, acetic acid and acetonitrile to obtain a crystal. The metal organic framework material shows potential application value of selectively adsorbing and separating carbon dioxide, methane and nitrogen.
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Paragraph 0022-0023; 0033
(2021/04/10)
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- COVALENT ORGANIC FRAMEWORKS AND APPLICATIONS AS PHOTOCATALYSTS
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Described herein are covalent organic frameworks. The covalent organic frameworks have unique structural and physical properties, which lends them to be versatile in a number of different applications and uses. In one aspect, the covalent organic frameworks are composed of a plurality of fused aromatic groups and electron-deficient chromophores. The covalent organic frameworks are useful as photocatalysts in a number of different applications.
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Paragraph 00126-00127
(2021/05/21)
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- (E)-1,2-Diphenylethene-based conjugated nanoporous polymers for a superior adsorptive removal of dyes from water
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Conjugated microporous polymers (CMPs) as prospective adsorbents for organic pollutant treatments are extremely appealing for both basic and applied kinds of research due to their simplicity, high performance, low cost, and processing under ambient conditions. However, the development of CMPs having excellent pollutant adsorption behaviour is still challenging. Herein, we described the targeted synthesis of a series of (E)-1,2-diphenylethene-based CMPs - BIPE-BIPE, BIPE-Py, and BIPE-TPT CMPs - via [4 + 4] and [4 + 3] Suzuki-Miyaura polymerizations of the novel (E)-1,2-bis(3,5-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethene (BITPE-4Bpin) with 1,2-bis(3,5-dibromophenyl)ethene (BIPE-4Br), 1,3,6,8-tetrabromopyrene (Py-4Br), and 2,4,6-tris(4-bromophenyl)-1,3,5-triazine (TPT-3Br), respectively. The porosities, chemical structures, and morphologies of the three CMPs were studied. The synthesized CMPs displayed high BET surface areas (up to 1400 m2 g-1) and outstanding thermal stabilities (up to a Td10 of 604 °C and char yield of 81 wt%). In addition, the as-prepared CMPs showed an extraordinarily high adsorption capacity for the organic dye rhodamine B (RhB) from water; the maximum adsorption capacity for RhB was 1027 mg g-1. Interestingly, our CMPs exhibited good recyclability and quickly attained 99.6% of their maximal adsorption capacity within 3 min. Our CMPs with the excellent adsorption behaviour could be good materials for water treatment and purification applications.
- El-Mahdy, Ahmed F. M.,Saber, Ahmed F.
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supporting information
p. 21834 - 21843
(2021/12/13)
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- MOF COMPOSITIONS FOR SELECTIVE SEPARATION OF HYDROCARBONS
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The present invention relates to novel metal-organic frameworks (MOFs) comprising tetratopic ligands with small pore apertures. The present invention further relates to methods of utilizing the MOFs of the invention to separate hydrocarbons through adsorptive processes.
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Page/Page column 30
(2020/04/25)
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- Imidazole-Linked Crystalline Two-Dimensional Polymer with Ultrahigh Proton-Conductivity
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Proton-exchange membrane fuel cells are promising energy devices for a sustainable future due to green features, high power density, and mild operating conditions. A facile proton-conducting membrane plays a pivotal role to boost the efficiency of fuel cells, and hence focused research in this area is highly desirable. Major issues associated with the successful example of Nafion resulted in the search for alternate proton conducting materials. Even though proton carrier loaded crystalline porous organic frameworks have been used for proton-conduction, the weak host-guest interactions limited their practical use. Herein, we developed a crystalline 2D-polymer composed of benzimidazole units as the integral part, prepared by the condensation of aryl acid and diamine in polyphosphoric acid medium. The imidazole linked-2D-polymer exhibits ultrahigh proton conductivity (3.2 × 10-2 S cm-1) (at 95% relative humidity and 95 °C) in the pristine state, which is highest among the undoped porous organic frameworks so far reported. The present strategy of a crystalline proton-conducting 2D-polymer will lead to the development of new high performing crystalline solid proton conductor.
- Ranjeesh, Kayaramkodath Chandran,Illathvalappil, Rajith,Veer, Sairam Dnyaneshwar,Peter, Joseph,Wakchaure, Vivek Chandrakant,Goudappagouda,Raj, K. Vipin,Kurungot, Sreekumar,Babu, Sukumaran Santhosh
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supporting information
p. 14950 - 14954
(2019/10/19)
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- Synthesis of 1,3,6,8-tetra-substituted pyrene derivatives and application of pyrene derivatives in organic field-effect transistors
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The invention aims to develop synthesis of 1,3,6,8-tetra-substituted pyrene derivatives of the same category having semiconductor properties and application of the derivatives in organic field-effecttransistors. Series thiophene units are introduced into positions 1, 3, 6 and 8 of pyrene to construct the tetra-substituted pyrene derivatives, and material preparation is performed by utilizing a chemical reaction. Moreover, a silicon wafer serves as a gate, and the pyrene derivatives serve as organic semiconductor materials, so that bottom-gate top-contact field-effect transistors are prepared.R refers to the following groups as shown in the specification.
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Paragraph 0013; 0017; 0020
(2019/10/01)
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- Biphenyl compound and application of biphenyl compound to preparation of 1,3,6,8-tetrabromopyrene
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The invention discloses a biphenyl compound and application of the biphenyl compound to preparation of 1,3,6,8-tetrabromopyrene.
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Paragraph 0065-0067; 0079-0081
(2018/06/04)
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- BODIPY-containing porous organic polymers for gas adsorption
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A series of BODIPY-containing microporous organic polymers was synthesized via a Sonogashira-Hagihara cross-coupling reaction of a BODIPY derivative with triple polymerisable groups and a range of aryl-alkyne monomers. All of the polymers show high isosteric heats of CO2 adsorption (23.3-27.3 kJ mol-1) because the incorporation of heteroatoms (N, B, F) from the BODIPY unit into the polymer skeleton enhanced the binding affinity between the pore wall and CO2 molecules. The aryl-alkyne monomer has a large influence on the surface area and CO2 adsorption performance of the resulting polymers. The polymer BDPCMP-3 shows a high Brunauer-Emmett-Teller specific surface area of up to 725 m2 g-1, while BDPCMP-2 with a low surface area of 582 m2 g-1 shows a high CO2 uptake ability of 2.25 mmol g-1 at 1.13 bar/273 K with a CO2/N2 adsorption selectivity of 32.3.
- Xu, Yunfeng,Chang, Dan,Feng, Shi,Zhang, Chong,Jiang, Jia-Xing
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supporting information
p. 9415 - 9423
(2016/11/11)
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- Synthetic Receptors for the High-Affinity Recognition of O-GlcNAc Derivatives
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The combination of a pyrenyl tetraamine with an isophthaloyl spacer has led to two new water-soluble carbohydrate receptors ("synthetic lectins"). Both systems show outstanding affinities for derivatives of N-acetylglucosamine (GlcNAc) in aqueous solution. One receptor binds the methyl glycoside GlcNAc-β-OMe with Ka≈20 000 m-1, whereas the other one binds an O-GlcNAcylated peptide with Ka≈70 000 m-1. These values substantially exceed those usually measured for GlcNAc-binding lectins. Slow exchange on the NMR timescale enabled structural determinations for several complexes. As expected, the carbohydrate units are sandwiched between the pyrenes, with the alkoxy and NHAc groups emerging at the sides. The high affinity of the GlcNAcyl-peptide complex can be explained by extra-cavity interactions, raising the possibility of a family of complementary receptors for O-GlcNAc in different contexts. Two carbohydrate receptors (see scheme) were prepared directly from a pyrenyl tetraamine and an isophthaloyl derivative. With extended aromatic surfaces linked by polar spacers, they are well suited to binding all-equatorial monosaccharides, showing especially high affinities for β-linked N-acetylglucosamine (GlcNAc).
- Rios, Pablo,Carter, Tom S.,Mooibroek, Tiddo J.,Crump, Matthew P.,Lisbjerg, Micke,Pittelkow, Michael,Supekar, Nitin T.,Boons, Geert-Jan,Davis, Anthony P.
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supporting information
p. 3387 - 3392
(2016/03/22)
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- Covalent attachment and release of small molecules from functional polyphenylene dendrimers
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Herein, we report the synthesis of 2nd generation PPDs functionalized with free thiol moieties within the scaffold, which were used as anchor points for the covalent attachment of guest species (p-nitrophenol derivatives) through the oxidative formation of disulfide linkages. The disulfide bonds were then cleaved under reductive conditions using dithiothreitol to discharge the molecules.
- Hammer, Brenton A. G.,Baumgarten, Martin,Muellen, Klaus
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supporting information
p. 2034 - 2036
(2014/03/21)
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- Synthesis, structural and spectral properties of diarylamino-functionalized pyrene derivatives via Buchwald-Hartwig amination reaction
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A new series of diarylamino-functionalized pyrene derivatives, namely, 1-(N,N-diarylamino)-substituted pyrenes (7), isomer of 1,6-bis- and 1,8-bis(N,N-diarylamino)-substituted pyrenes (8/9) and 1,3,6,8-tetrakis(N,N- diarylamino)-substituted pyrenes (10) have been synthesized. The structures of these synthesized compounds were determined on the basis of spectral data and elemental analysis. All compounds 7-10 have bright fluorescent emissions from sky-blue to green in solution condition (λmax = 464-500 nm in CH2Cl2) and high emission efficiency (Φf = 0.84-0.96 in dichloromethane). All compounds have high thermal stability and good solubility in common organic solvents. The electronic properties of these compounds were determined by spectroscopic methods such as UV-vis absorption spectroscopy and fluorescence emission spectroscopy. Clear evidences were obtained that the longest wavelength bands of these compounds are bathochromically red-shifted as the number of the diarylamino-substituent increased.
- Hu, Jian-Yong,Feng, Xing,Seto, Nobuyuki,Do, Jung-Hee,Zeng, Xi,Tao, Zhu,Yamato, Takehiko
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- Blue-emitting butterfly-shaped 1,3,5,9-tetraarylpyrenes: Synthesis, crystal structures, and photophysical properties
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The first example of aryl-functionalized, butterfly-shaped, highly fluorescent and stable blue-emitting monomers, namely, 7-tert-butyl-1,3,5,9- tetrakis(p-R-phenyl)pyrenes, were synthesized by the Suzuki-Miyaura cross-coupling reaction from a novel bromide precursor of 1,3,5,9-tetrabromo-7- tert-butylpyrene. The crystal structures and optical and electronic properties have been investigated.
- Feng, Xing,Hu, Jian-Yong,Iwanaga, Fumitaka,Seto, Nobuyuki,Redshaw, Carl,Elsegood, Mark R. J.,Yamato, Takehiko
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supporting information
p. 1318 - 1321
(2013/04/24)
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- CONDENSED-CYCLIC COMPOUND AND ORGANIC LIGHT EMITTING DIODE INCLUDING THE SAME
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Embodiments of the present invention are directed to a condensed-cyclic compound and an OLED including the same.
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Paragraph 0156; 0157
(2013/07/19)
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- Efficient modification of pyrene-derivative featuring third-order nonlinear optics via the click post-functionalization
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A series of pyrene derivatives featuring nonplanar structures of N,N-didodecylanilino-substituted donor and TCNE/TCNQ adduct acceptors have been efficiently synthesized via formal [2+2] cycloaddition. As the efficient click by TCNE and TCNQ, the products show strong charge-transfer (CT) bands in the visible (near-IR region), potent redox activities, and related photophysical properties. UV/vis spectra and electrochemical studies show that the CT properties of these systems are readily tunable by strong cyano acceptor introduction on the nucleophile, which have a larger effect on the lowest unoccupied molecular orbital (LUMO). In particular, compared with the adduct of TCNE, the product clicked with TCNQ possessed a stronger D-A conjugation and bulkier π spacers. The TCNQ product also has a larger third-order nonlinear optical property which was characterized by Z-scan experiments. This could point to potentially interesting applications of the new pyrene derivatives in optoelectronic devices and develop the new modification process for the design of different pyrene-based molecular electronic devices.
- Jin, Zhaokui,Wang, Dong,Wang, Xiangke,Liang, Pengxia,Mi, Yongsheng,Yang, Huai
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supporting information
p. 4859 - 4864
(2013/09/02)
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- 1,3,6,8-TETRASUBSTITUTED PYRENE COMPOUNDS, ORGANIC EL DEVICE AND ORGANIC EL DISPLAY
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The object of the present invention is to provide organic electroluminescent elements that are excellent in luminous efficiency, luminance, and color purity and exhibit long lifetime. The organic EL elements according to the present invention comprise an organic thin layer between a positive electrode and a negative electrode, and the organic thin layer comprises a 1,3,6,8-tetrasubstituted pyrene compound expressed by the formula (1) as the light emitting material, wherein R 1 to R 4 in the formula (1) may be identical or different each other, and are each a group expressed by the formula (2): wherein R 5 to R 9 in the formula (2) may be identical or different each other, are each a hydrogen atom or a substituted group; and at least one of R 5 to R 9 is a substituted or unsubstituted aryl group.
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Page/Page column
(2013/09/26)
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- Design and preparation of platinum-acetylide organogelators containing ethynyl-pyrene moieties as the main skeleton
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A series of new platinum-acetylide complexes containing ethynyl-pyrene moieties as the main skeleton were synthesized and characterized. The investigation of the absorption and emission spectra of these complexes revealed that the extension of the molecular size with the introduction of different numbered platinum-acetylide fragments can efficiently tune the absorption and emission bands from the UV to the longer wavelength region. Moreover, the gelation properties of these complexes were investigated by the "stable-to-inversion-of-a-test-tube" method. Most newly designed platinum-acetylide compounds presented a stable gel-formation property in some of the tested solvents. The morphology of the xerogels was investigated by scanning electron microscopy (SEM). Furthermore, the concentration- and temperature-dependent absorption and emission properties of these complexes were investigated, which support the formation of J-type assemblies during the aggregation process. More importantly, it was found that the complexes 4 a-C6, 4 a, and 4 a-C18 with four platinum-acetylide fragments presented potential applications as luminescent organometallic gels.
- Xu, Xing-Dong,Zhang, Jing,Yu, Xudong,Chen, Li-Jun,Wang, De-Xian,Yi, Tao,Li, Fuyou,Yang, Hai-Bo
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p. 16000 - 16013
(2013/02/23)
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- A visible light excitable "on-off" and "green-red" fluorescent chemodosimeter for Ni2+/Pb2+
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A pyrene derivative has been synthesized as a visible light excitable fluorescent chemodosimeter which exhibits "on-off" and "green-red" fluorescence behavior for Ni2+ and Pb 2+ with different reaction speed, respectively, and its sensing ability toward metal cations and counter ions was investigated in detail. The high selectivity of the 'in situ' prepared Ni2+ and Pb2+ complexes toward EDA and the reaction speed difference provide two new effective methods for distinguishing between Ni2+ and Pb2+. The Royal Society of Chemistry and the Centre National de la Recherche Scientifique.
- Wang, Lina,Yu, Mingming,Liu, Zhenting,Zhao, Wanying,Li, Zhanxian,Ni, Zhonghai,Li, Changchun,Wei, Liuhe
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p. 2176 - 2179
(2013/01/15)
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- Highly sensitive phototransistor with crystalline microribbons from new π-extended pyrene derivative via solution-phase self-assembly
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A new pyrene-cored π-conjugated molecule has been synthesized through Sonogashira coupling reaction. The single-crystalline microribbon-based FET exhibited the highest mobility of 0.7 cm2 V-1 s -1 (Ion/Ioff > 106). Single-crystalline microribbons were employed to operate in an organic phototransistor (OPT) under very low light intensity (I = 5.6 μW cm -2).
- Sun Kim, Youn,Young Bae, Suk,Hwan Kim, Kyung,Wan Lee, Tae,Hur, Jung A.,Ha Hoang, Mai,Ju Cho, Min,Kim, Sung-Jin,Kim, Youngmee,Kim, Minsik,Lee, Kwangyeol,Joong Lee, Suk,Hoon Choi, Dong
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supporting information; experimental part
p. 8907 - 8909
(2011/09/21)
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- Pyrene-cored dendrimer with carbazole derivatives as dendrons: Synthesis, properties and application in white light-emitting diode
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A new dendrimer using pyrene as core and carbazole derivative as dendron has been successfully prepared via Suzuki coupling reaction. Its chemical structure was confirmed through 1H NMR, elemental analysis and MALDI-TOF MS methods. The dendrimer synthesized possessed excellent thermal stability with initial decomposition temperature over 470 °C and high fluorescence quantum yield of 86%. The luminescence spectra showed that, relative to the solution sample, the emission peaks of the solid dendrimer film were apparently broadened and red-shifted, indicating the strong π-π stacking effect between the pyrene moieties. By doping 1.5% of the dendrimer in 4,4′-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB), a light-emitting diode device was fabricated in the ITO/NPB/NPB:dendrimer (1.5%)/TPBI/Mg:Ag configuration, which emitted a white color with Commission Internationale de L'Eclairage (CIEx,y) coordinates of (0.29, 0.34) and a maximum brightness of 1300 cd m-2, exhibiting promising potential in white light-emitting diode application. This journal is the Owner Societies.
- You, Jia,Li, Guiyang,Wang, Renjie,Nie, Qiuping,Wang, Zhonggang,Li, Jiuyan
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experimental part
p. 17825 - 17830
(2012/07/17)
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