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1.
Tian Du Ruiheng Gao Dr. Yunfeng Deng Cheng Wang Qian Zhou Prof. Yanhou Geng 《Angewandte Chemie (Weinheim an der Bergstrasse, Germany)》2020,132(1):227-231
A series of 1,3-indandione-terminated π-conjugated quinoids were synthesized by alkoxide-mediated rearrangement reaction of the respective alkene precursors, followed by air oxidation. This new protocol allows access to quinoidal compounds with variable termini and cores. The resulting quinoids all show LUMO levels below −4.0 eV and molar extinction coefficients above 105 L mol−1 cm−1. The optoelectronic properties of these compounds can be regulated by tuning the central cores as well as the aryl termini ascribed to the delocalized frontier molecular orbitals over the entire molecular skeleton involving aryl termini. n-Channel organic thin-film transistors with electron mobility of up to 0.38 cm2 V−1 s−1 were fabricated, showing the potential of this new class of quinoids as organic semiconductors. 相似文献
2.
Thieno[3,4‐c]pyrrole‐4,6‐dione‐Based Small Molecules for Highly Efficient Solution‐Processed Organic Solar Cells
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Jong‐jin Ha Yu Jin Kim Jong‐gwang Park Tae Kyu An Prof. Soon‐Ki Kwon Prof. Chan Eon Park Prof. Yun‐Hi Kim 《化学:亚洲杂志》2014,9(4):1045-1053
Two small molecules named BT‐TPD and TBDT‐TTPD with a thieno[3,4‐c]pyrrole‐4,6‐dione (TPD) unit were designed and synthesized for solution‐processed bulk‐heterojunction solar cells. Their thermal, electrochemical, optical, charge‐transport, and photovoltaic characteristics were investigated. These compounds exhibit strong absorption at 460–560 nm and low highest occupied molecular orbital levels (?5.36 eV). Field‐effect hole mobilities of these compounds are 1.7–7.7×10?3 cm2 V?1 s?1. Small‐molecule organic solar cells based on blends of these donor molecules and a acceptor display power conversion efficiencies as high as 4.62 % under the illumination of AM 1.5G, 100 mW cm?2. 相似文献
3.
Synthesis,Properties, and n‐Type Transistor Characteristics of π‐Conjugated Compounds Having a Carbonyl‐Bridged Thiazole‐Fused Polycyclic System
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Prof. Yutaka Ie Chihiro Sato Dr. Masashi Nitani Prof. Hirokazu Tada Prof. Yoshio Aso 《Chemistry (Weinheim an der Bergstrasse, Germany)》2014,20(50):16509-16515
A series of electron‐deficient π‐conjugated systems with 4,9‐dihydro‐s‐indaceno[2,1‐d:6,5‐d′]dithiazole‐4,9‐dione‐based structures and fluorinated acyl groups as the terminal units have been designed and synthesized for application as organic field‐effect transistor (OFET) materials. The thermal, photophysical, and electrochemical properties and OFET performance of the synthesized compounds were investigated. OFET evaluation revealed that all compounds exhibited typical electron‐transporting characteristics, and electron mobilities up to 0.26 cm2 V?1 s?1 could be achieved. The air stabilities of OFET operation were dependent on the nature of the compounds and were investigated by X‐ray diffraction and atomic force microscopy. The terminal units had a great influence not only on the molecular properties, but also on the film‐forming properties and OFET performance. 相似文献
4.
Feng‐Yang Shih Deokkyu Choi Qin Wu Chang‐Yong Nam Robert B. Grubbs 《Angewandte Chemie (Weinheim an der Bergstrasse, Germany)》2019,131(1):294-297
ipso‐Arylative ring‐opening polymerization of 2‐bromo‐8‐aryl‐8H‐indeno[2,1‐b]thiophen‐8‐ol monomers proceeds to Mn up to 9 kg mol?1 with conversion of the monomer diarylcarbinol groups to pendent conjugated aroylphenyl side chains (2‐benzoylphenyl or 2‐(4‐hexylbenzoyl)phenyl), which influence the optical and electronic properties of the resulting polythiophenes. Poly(3‐(2‐(4‐hexylbenzoyl)phenyl)thiophene) was found to have lower frontier orbital energy levels (HOMO/LUMO=?5.9/?4.0 eV) than poly(3‐hexylthiophene) owing to the electron‐withdrawing ability of the aryl ketone side chains. The electron mobility (ca. 2×10?3 cm2 V?1 s?1) for poly(3‐(2‐(4‐hexylbenzoyl)phenyl)thiophene) was found to be significantly higher than the hole mobility (ca. 8×10?6 cm2 V?1 s?1), which suggests such polymers are candidates for n‐type organic semiconductors. Density functional theory calculations suggest that backbone distortion resulting from side‐chain steric interactions could be a key factor influencing charge mobilities. 相似文献
5.
Enhanced Performance of Benzothieno[3,2‐b]thiophene (BTT)‐Based Bottom‐Contact Thin‐Film Transistors
Dr. Peng‐Yi Huang Dr. Liang‐Hsiang Chen Yu‐Yuan Chen Wen‐Jung Chang Juin‐Jie Wang Dr. Kwang‐Hwa Lii Dr. Jing‐Yi Yan Dr. Jia‐Chong Ho Dr. Cheng‐Chung Lee Prof. Choongik Kim Prof. Ming‐Chou Chen 《Chemistry (Weinheim an der Bergstrasse, Germany)》2013,19(11):3721-3728
Three new benzothieno[3,2‐b]thiophene ( BTT ; 1 ) derivatives, which were end‐functionalized with phenyl ( BTT‐P ; 2 ), benzothiophenyl ( BTT‐BT ; 3 ), and benzothieno[3,2‐b]thiophenyl groups ( BBTT ; 4 ; dimer of 1 ), were synthesized and characterized in organic thin‐film transistors (OTFTs). A new and improved synthetic method for BTT s was developed, which enabled the efficient realization of new BTT ‐based semiconductors. The crystal structure of BBTT was determined by single‐crystal X‐ray diffraction. Within this family, BBTT , which had the largest conjugation of the BTT derivatives in this study, exhibited the highest p‐channel characteristic, with a carrier mobility as high as 0.22 cm2 V?1 s?1 and a current on/off ratio of 1×107, as well as good ambient stability for bottom‐contact/bottom‐gate OTFT devices. The device characteristics were correlated with the film morphologies and microstructures of the corresponding compounds. 相似文献
6.
Gaobo Lin Lingna Wang Yizhou Yang Zitong Liu Guanxin Zhang Deqing Zhang 《化学:亚洲杂志》2019,14(10):1712-1716
Conjugated molecules with low lying LUMO levels are demanding for the development of air stable n‐type organic semiconductors. In this paper, we report a new A‐D‐A′‐D‐A conjugated molecule ( DAPDCV ) entailing diazapentalene (DAP) and dicyanovinylene groups as electron accepting units. Both theoretical and electrochemical studies manifest that the incorporation of DAP unit in the conjugated molecule can effectively lower the LUMO energy level. Accordingly, thin film of DAPDCV shows n‐type semiconducting behavior with electron mobility up to 0.16 cm2?V?1?s?1 after thermal annealing under N2 atmosphere. Moreover, thin film of DAPDCV also shows stable n‐type transporting property in air with mobility reaching 0.078 cm2?V?1?s?1. 相似文献
7.
Triazole‐Substituted Nitroarene Derivatives: Synthesis,Characterization, and Energetic Studies
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Nagarjuna Kommu Vikas D. Ghule A. Sudheer Kumar Prof. Dr. Akhila K. Sahoo 《化学:亚洲杂志》2014,9(1):166-178
A series of dense and energetic polynitroaryl‐1,2,4‐triazoles were synthesized through the nitration of aryl‐1,2,4‐triazoles. The Cu‐catalyzed/base‐mediated coupling reactions of haloarenes with 1,2,4‐triazoles delivered N‐aryl‐1,2,4‐triazoles. These new nitro‐rich‐aryltriazoles were characterized by analytical and spectroscopic methods. The solid‐state structures of most of these compounds were established by X‐ray diffraction analysis. Their thermal properties were determined by differential scanning calorimetry–thermogravimetric analysis. Their heats of formation (HOFs) and crystal densities were also calculated. The densities of the synthesized compounds ranged from 1.40 to 1.85 g cm?3. Some of these newly synthesized compounds exhibited high positive HOFs, good thermal stabilities, high densities, and reasonable detonation velocities and pressures. 相似文献
8.
Hydrogen‐Bonded Organic Frameworks (HOFs): A New Class of Porous Crystalline Proton‐Conducting Materials
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Avishek Karmakar Rajith Illathvalappil Bihag Anothumakkool Arunabha Sen Partha Samanta Aamod V. Desai Dr. Sreekumar Kurungot Dr. Sujit K. Ghosh 《Angewandte Chemie (International ed. in English)》2016,55(36):10667-10671
Two porous hydrogen‐bonded organic frameworks (HOFs) based on arene sulfonates and guanidinium ions are reported. As a result of the presence of ionic backbones appended with protonic source, the compounds exhibit ultra‐high proton conduction values (σ) 0.75× 10?2 S cm?1 and 1.8×10?2 S cm?1 under humidified conditions. Also, they have very low activation energy values and the highest proton conductivity at ambient conditions (low humidity and at moderate temperature) among porous crystalline materials, such as metal–organic frameworks (MOFs) and covalent organic frameworks (COFs). These values are not only comparable to the conventionally used proton exchange membranes, such as Nafion used in fuel cell technologies, but is also the highest value reported in organic‐based porous architectures. Notably, this report inaugurates the usage of crystalline hydrogen‐bonded porous organic frameworks as solid‐state proton conducting materials. 相似文献
9.
Pd Nanocubes@ZIF‐8: Integration of Plasmon‐Driven Photothermal Conversion with a Metal–Organic Framework for Efficient and Selective Catalysis
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Qihao Yang Prof. Dr. Qiang Xu Prof. Dr. Shu‐Hong Yu Prof. Dr. Hai‐Long Jiang 《Angewandte Chemie (International ed. in English)》2016,55(11):3685-3689
Composite nanomaterials usually possess synergetic properties resulting from the respective components and can be used for a wide range of applications. In this work, a Pd nanocubes@ZIF‐8 composite material has been rationally fabricated by encapsulation of the Pd nanocubes in ZIF‐8, a common metal–organic framework (MOF). This composite was used for the efficient and selective catalytic hydrogenation of olefins at room temperature under 1 atm H2 and light irradiation, and benefits from plasmonic photothermal effects of the Pd nanocube cores while the ZIF‐8 shell plays multiple roles; it accelerates the reaction by H2 enrichment, acts as a “molecular sieve” for olefins with specific sizes, and stabilizes the Pd cores. Remarkably, the catalytic efficiency of a reaction under 60 mW cm?2 full‐spectrum or 100 mW cm?2 visible‐light irradiation at room temperature turned out to be comparable to that of a process driven by heating at 50 °C. Furthermore, the catalyst remained stable and could be easily recycled. To the best of our knowledge, this work represents the first combination of the photothermal effects of metal nanocrystals with the favorable properties of MOFs for efficient and selective catalysis. 相似文献
10.
Tom E. Stennett Philipp Bissinger Stefanie Griesbeck Stefan Ullrich Ivo Krummenacher Michael Auth Andreas Sperlich Matthias Stolte Krzysztof Radacki Chang‐Jiang Yao Frank Würthner Andreas Steffen Todd B. Marder Holger Braunschweig 《Angewandte Chemie (International ed. in English)》2019,58(19):6449-6454
Herein, two new quadrupolar acceptor‐π‐donor‐π‐acceptor (A‐π‐D‐π‐A) chromophores have been prepared featuring a strongly electron‐donating diborene core and strongly electron‐accepting dimesitylboryl (BMes2) and bis(2,4,6‐tris(trifluoromethyl)phenyl)boryl (BFMes2) end groups. Analysis of the compounds by NMR spectroscopy, X‐ray crystallography, cyclic voltammetry, and UV/Vis‐NIR absorption and emission spectroscopy indicated that the compounds have extended conjugated π‐systems spanning their B4C8 cores. The combination of exceptionally potent π‐donor (diborene) and π‐acceptor (diarylboryl) groups, both based on trigonal boron, leads to very small HOMO–LUMO gaps, resulting in strong absorption in the near‐IR region with maxima in THF at 840 and 1092 nm and very high extinction coefficients of ca. 120 000 m ?1 cm?1. Both molecules also display weak near‐IR fluorescence with small Stokes shifts. 相似文献
11.
Ernesto C. Tuazon Pilar Martin Sara M. Aschmann Janet Arey Roger Atkinson 《国际化学动力学杂志》2011,43(11):631-638
Rate constants for the reactions of 2‐methoxy‐6‐(trifluoromethyl)pyridine, diethylamine, and 1,1,3,3,3‐pentamethyldisiloxan‐1‐ol with OH radicals have been measured at 298 ± 2 K using a relative rate method. The measured rate constants (cm3 molecule?1 s?1) are (1.54 ± 0.21) × 10?12 for 2‐methoxy‐6‐(trifluoromethyl)pyridine, (1.19 ± 0.25) × 10?10 for diethylamine, and (1.76 ± 0.38) × 10?12 for 1,1,3,3,3‐pentamethyldisiloxan‐1‐ol, where the indicated errors are the estimated overall uncertainties including those in the rate constants for the reference compounds. No reaction of 2‐methoxy‐6‐(trifluoromethyl)pyridine with gaseous nitric acid was observed, and an upper limit to the rate constant for the reaction of 1,1,3,3,3‐pentamethyldisiloxan‐1‐ol with O3 of <7 × 10? 20 cm3 molecule?1 s?1 was determined. Using a 12‐h average daytime OH radical concentration of 2 × 106 molecule cm?3, the lifetimes of the volatile organic compounds studied here with respect to reaction with OH radicals are 7.5 days for 2‐methoxy‐6‐(trifluoromethyl)pyridine, 1.2 h for diethylamine, and 6.6 days for 1,1,3,3,3‐pentamethyldisiloxan‐1‐ol. Likely reaction mechanisms are discussed. © 2011 Wiley Periodicals, Inc. Int J Chem Kinet 43: 631–638, 2011 相似文献
12.
EDOT‐diketopyrrolopyrrole copolymers for high bulk hole mobility and near infrared absorption
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Christian J. Mueller Chetan R. Singh Mukundan Thelakkat 《Journal of Polymer Science.Polymer Physics》2016,54(6):639-648
To obtain novel low‐bandgap materials with tailored hole‐transport properties and extended absorption, electron rich 3,4‐ethylenedioxythiophene is introduced as a comonomer in diketopyrrolo[3,4‐c]pyrrole copolymers with different aryl flanking units. The polymers are characterized by absorption and photoluminescence spectroscopy, dynamic scanning calorimetry, cyclic voltammetry, and X‐ray diffraction. The charge transport properties of these new materials are studied carefully using an organic field effect transistor geometry where the charge carriers are transported over a narrow channel at the semiconductor/dielectric interface. These results are compared to bulk charge carrier mobilities using space‐charge limited current (SCLC) measurements, in which the charge carrier is transported through the complete film thickness of several hundred nanometers. Finally, charge carrier mobilities are correlated with the electronic structure of the compounds. We find that in particular the thiophene‐flanked copolymer PDPP[T]2‐EDOT is a very promising candidate for organic photovoltaics, showing an absorption response in the near infrared region with an optical bandgap of 1.15 eV and a very high bulk hole mobility of 2.9 × 10?4 cm2 V?1 s?1 as measured by SCLC. This value is two orders of magnitudes higher than SCLC mobilities reported for other polydiketopyrrolopyrroles and is in the range of the well‐known hole transporting polymer poly(3‐hexylthiophene). © 2015 Wiley Periodicals, Inc. J. Polym. Sci., Part B: Polym. Phys. 2016 , 54, 639–648 相似文献
13.
Joseph A. Letizia Dr. Scott Cronin Rocio Ponce Ortiz Dr. Antonio Facchetti Dr. Mark A. Ratner Prof. Tobin J. Marks Prof. 《Chemistry (Weinheim an der Bergstrasse, Germany)》2010,16(6):1911-1928
Electron‐transporting organic semiconductors (n‐channel) for field‐effect transistors (FETs) that are processable in common organic solvents or exhibit air‐stable operation are rare. This investigation addresses both these challenges through rational molecular design and computational predictions of n‐channel FET air‐stability. A series of seven phenacyl–thiophene‐based materials are reported incorporating systematic variations in molecular structure and reduction potential. These compounds are as follows: 5,5′′′‐bis(perfluorophenylcarbonyl)‐2,2′:5′,‐ 2′′:5′′,2′′′‐quaterthiophene ( 1 ), 5,5′′′‐bis(phenacyl)‐2,2′:5′,2′′: 5′′,2′′′‐quaterthiophene ( 2 ), poly[5,5′′′‐(perfluorophenac‐2‐yl)‐4′,4′′‐dioctyl‐2,2′:5′,2′′:5′′,2′′′‐quaterthiophene) ( 3 ), 5,5′′′‐bis(perfluorophenacyl)‐4,4′′′‐dioctyl‐2,2′:5′,2′′:5′′,2′′′‐quaterthiophene ( 4 ), 2,7‐bis((5‐perfluorophenacyl)thiophen‐2‐yl)‐9,10‐phenanthrenequinone ( 5 ), 2,7‐bis[(5‐phenacyl)thiophen‐2‐yl]‐9,10‐phenanthrenequinone ( 6 ), and 2,7‐bis(thiophen‐2‐yl)‐9,10‐phenanthrenequinone, ( 7 ). Optical and electrochemical data reveal that phenacyl functionalization significantly depresses the LUMO energies, and introduction of the quinone fragment results in even greater LUMO stabilization. FET measurements reveal that the films of materials 1 , 3 , 5 , and 6 exhibit n‐channel activity. Notably, oligomer 1 exhibits one of the highest μe (up to ≈0.3 cm2 V?1 s?1) values reported to date for a solution‐cast organic semiconductor; one of the first n‐channel polymers, 3 , exhibits μe≈10?6 cm2 V?1 s?1 in spin‐cast films (μe=0.02 cm2 V?1 s?1 for drop‐cast 1 : 3 blend films); and rare air‐stable n‐channel material 5 exhibits n‐channel FET operation with μe=0.015 cm2 V?1 s?1, while maintaining a large Ion:off=106 for a period greater than one year in air. The crystal structures of 1 and 2 reveal close herringbone interplanar π‐stacking distances (3.50 and 3.43 Å, respectively), whereas the structure of the model quinone compound, 7 , exhibits 3.48 Å cofacial π‐stacking in a slipped, donor‐acceptor motif. 相似文献
14.
Man Ge Jie Feng Hailian Huang Xiaofeng Gou Chengwen Hua Bang Chen Junlong Zhao 《Journal of heterocyclic chemistry》2019,56(12):3297-3302
Six novel derivatives of 2‐ferrocenyl‐5‐aryl‐1,3,4‐oxadiazoles have been synthesized through catalytic oxidation of benzoylhydrazone with nitrophthalocyanine iron (II) as catalyst and tert‐butyl hydroperoxide as oxidant. All of the compounds have been characterized by high‐resolution mass spectrometry, 1H, 13C NMR, and infrared spectroscopy. Moreover, the antifungal activities of all new compounds have been evaluated and the results showed that the compounds exhibited excellent antifungal activities. In addition, the molecular structure of compound 1c could also be determined by X‐ray single‐crystal diffraction. 相似文献
15.
Thienoisoindigo‐based small molecules and narrow bandgap polymers synthesized via C–H direct arylation coupling
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Jing Huang Kai Wang Sukriti Gupta Guojie Wang Cangjie Yang Samir H. Mushrif Mingfeng Wang 《Journal of polymer science. Part A, Polymer chemistry》2016,54(13):2015-2031
Thienoisoindigo (TIIG) has emerged as an attractive building block for high‐performance organic optoelectronic devices. Here we report the first synthesis of a series of π‐conjugated TIIG‐based small molecules and alternating copolymers via direct C–H arylation, which enables the efficient synthesis without use of flammable and toxic orgametallic reagents in fewer steps compared Suzuki and Stille coupling. The direct arylation coupling between TIIG and two respective mono‐bromo aryl reactants clearly shows that the α‐H is more reactive than the β‐H in the thiophene unit of TIIG. The high regioselectivity of TIIG monomer warrants the successful synthesis of high‐quality alternating copolymers with minimal structural defects. PTIIG‐BT polymer synthesized via direct arylation polymerization (DAP) showed comparable molecular weight and hole mobility than the same polymer previously synthesized via Suzuki coupling. Moreover, the two new polymers (PTIIG‐TF and PTIIG‐2FBT) synthesized via DAP showed hole mobility up to 10?3 cm2 V?1 s?1 in FET devices fabricated and tested under ambient conditions. © 2016 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2016 , 54, 2015–2031 相似文献
16.
Yuta Nohara Junpei Kuwabara Takeshi Yasuda Liyuan Han Takaki Kanbara 《Journal of polymer science. Part A, Polymer chemistry》2014,52(10):1401-1407
A naphthalenediimide (NDI)‐based conjugated polymer was synthesized by a two‐step direct C‐H arylation sequence. In the first step, two ethylenedioxythiophene units were coupled to NDI by direct arylation. In the second step, the direct arylation polycondensation of the monomer, formed in the first step, with 2,7‐dibromo‐9,9‐dioctylfluorene afforded the corresponding NDI‐based conjugated polymer ( PEDOTNDIF ) with molecular weight of 21,500 in 91% yield. The optical and electrochemical properties of the polymer were evaluated. The polymer showed ambipolar behavior in organic field‐effect transistors (OFETs). The electron mobility of PEDOTNDIF was estimated to be 2.3 × 10?6 cm2 V?1 s?1 using an OFET device with source‐drain (S‐D) Au electrodes. A modified OFET device with S‐D MgAg electrodes increased the electron mobility for PEDOTNDIF to 1.0 × 10?5 cm2 V?1 s?1 due to the more suitable work function of these electrodes, which reduced the injection barrier to the semiconducting polymer. © 2014 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2014 , 52, 1401–1407 相似文献
17.
A Diradical Approach towards BODIPY‐Based Dyes with Intense Near‐Infrared Absorption around λ=1100 nm
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Dr. Yong Ni Sangsu Lee Minjung Son Prof. Dr. Naoki Aratani Masatoshi Ishida Dr. Animesh Samanta Prof. Dr. Hiroko Yamada Prof. Dr. Young‐Tae Chang Prof. Dr. Hiroyuki Furuta Prof. Dr. Dongho Kim Prof. Dr. Jishan Wu 《Angewandte Chemie (International ed. in English)》2016,55(8):2815-2819
A diradical approach to obtain stable organic dyes with intense absorption around λ=1100 nm is reported. The para‐ and meta‐quinodimethane‐bridged BODIPY dimers BD‐1 and BD‐2 were synthesized and were found to have a small amount of diradical character. These molecules exhibited very intense absorption at λ=1088 nm (?=6.65×105 M ?1 cm?1) and 1136 nm (?=6.44×105 M ?1 cm?1), respectively, together with large two‐photon‐absorption cross‐sections. Structural isomerization induced little variation in their diradical character but distinctive differences in their physical properties. Moreover, the compounds showed a selective fluorescence turn‐on response in the presence of the hydroxyl radical but not with other reactive oxygen species. 相似文献
18.
From Linear to Angular Isomers: Achieving Tunable Charge Transport in Single‐Crystal Indolocarbazoles Through Delicate Synergetic CH/NH⋅⋅⋅π Interactions
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Dr. Hui Jiang Dr. Peng Hu Dr. Jun Ye Dr. Apoorva Chaturvedi Dr. Keke K. Zhang Yongxin Li Dr. Yi Long Prof. Denis Fichou Prof. Christian Kloc Prof. Wenping Hu 《Angewandte Chemie (International ed. in English)》2018,57(29):8875-8880
Weak intermolecular interaction in organic semiconducting molecular crystals plays an important role in molecular packing and electronic properties. Here, four five‐ring‐fused isomers were rationally designed and synthesized to investigate the isomeric influence of linear and angular shapes in affecting their molecular packing and resultant electronic properties. Single‐crystal field‐effect transistors showed mobility order of 5,7‐ICZ (3.61 cm2 V?1 s?1) >5,11‐ICZ (0.55 cm2 V?1 s?1) >11,12‐ICZ (ca. 10?5 cm2 V?1 s?1) and 5,12‐ICZ (ca. 10?6 cm2 V?1 s?1). Theoretical calculations based on density functional theory (DFT) and polaron transport model revealed that 5,7‐ICZ can reach higher mobilities than the others thanks to relatively higher hole transfer integral that links to stronger intermolecular interaction due to the presence of multiple NH???π and CH???π(py) interactions with energy close to common NH???N hydrogen bonds, as well as overall lower hole‐vibrational coupling owing to the absence of coupling of holes to low frequency modes due to better π conjugation. 相似文献
19.
Alleno‐Acetylenic Cage (AAC) Receptors: Chiroptical Switching and Enantioselective Complexation of trans‐1,2‐Dimethylcyclohexane in a Diaxial Conformation
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Cornelius Gropp Dr. Nils Trapp Prof. Dr. François Diederich 《Angewandte Chemie (International ed. in English)》2016,55(46):14444-14449
Four enantiopure 1,3‐diethynylallenes (DEAs) with OH termini were attached to the rim of a resorcin[4]arene cavitand. The system undergoes conformational switching between a cage form, closed by a circular H‐bonding array, and an open form, with the tertiary alcohol groups reaching outwards. The cage form is predominant in apolar solvents, and the open conformation in small, polar solvents. Both states were confirmed in solution and in X‐ray co‐crystal structures. ECD spectra of the alleno‐acetylenic cages (AACs) are highly conformation sensitive, the longest wavelength Cotton effect at 304 nm switches from Δ?=+191 m ?1 cm?1 for open (P)4‐AAC?acetonitrile to Δ?=?691 m ?1 cm?1 (ΔΔ?=882 m ?1 cm?1) for closed (P)4‐AAC?cyclohexane. Complete chiral resolution of (±)‐trans‐1,2‐dimethylcyclohexane was found in the X‐ray structures, with (P)4‐AAC exclusively bound to the (R,R)‐ and (M)4‐AAC to the (S,S)‐guest. Guest inclusion occurs in a higher energy diaxial conformation. 相似文献
20.
Hui Li Peng Tang Yan Zhao Shi‐Xia Liu Yves Aeschi Lijun Deng Jörg Braun Bin Zhao Yunqi Liu Songting Tan Wolfgang Meier Silvio Decurtins 《Journal of polymer science. Part A, Polymer chemistry》2012,50(14):2935-2943
Two well‐defined alternating π‐conjugated polymers containing a soluble electroactive benzo[1,2‐b:4,5‐b′]difuran (BDF) chromophore, poly(BDF‐(9‐phenylcarbazole)) (PBDFC), and poly(BDF‐benzothiadiazole) (PBDFBTD) were synthesized via Sonogashira copolymerizations. Their optical, electrochemical, and field‐effect charge transport properties were characterized and compared with those of the corresponding homopolymer PBDF and random copolymers of the same overall composition. All these polymers cover broad optical absorption ranges from 250 to 750 nm with narrow optical band gaps of 1.78–2.35 eV. Both PBDF and PBDFBTD show ambipolar redox properties with HOMO levels of ?5.38 and ?5.09 eV, respectively. The field‐effect mobility of holes varies from 2.9 × 10?8 cm2 V?1 s?1 in PBDF to 1.0 × 10?5 cm2 V?1 s?1 in PBDFBTD. Bulk heterojunction solar cell devices were fabricated using the polymers as the electron donor and [6,6]‐phenyl‐C61‐butyric acid methyl ester as the electron acceptor, leading to power conversion efficiencies of 0.24–0.57% under air mass 1.5 illumination (100 mW cm?2). These results indicate that their band gaps, molecular electronic energy levels, charge mobilities, and molecular weights are readily tuned by copolymerizing the BDF core with different π‐conjugated units. © 2012 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2012 相似文献