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1,6‐ and 1,7‐Regioisomers of Dicyano‐Substituted Perylene Bisimides: Synthesis,Optical and Electrochemical Properties 下载免费PDF全文
In this study, 1,6‐ ad 1,7‐regioisomers of dicyano‐substituted perylene bisimides (1,6‐ C and 1,7‐ C ) were synthesized and successfully isolated from their regioisomeric mixture using conventional methods of separation, and subsequently characterized by 400 MHz 1H NMR spectroscopy. This is the first time that the 1,6‐dicyanoperylene bisimide 1,6‐ C has been obtained in pure form. Moreover, the optical and electrochemical properties of 1,6‐ C and 1,7‐ C were found to be virtually the same. Time‐dependent density functional theory calculations performed on both dyes are reported in order to rationalize their electronic structures and optical properties. 相似文献
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Solution‐Grown Organic Single‐Crystalline Donor–Acceptor Heterojunctions for Photovoltaics 下载免费PDF全文
Prof. Hanying Li Congcheng Fan Weifei Fu Dr. Huolin L. Xin Prof. Hongzheng Chen 《Angewandte Chemie (International ed. in English)》2015,54(3):956-960
Organic single crystals are ideal candidates for high‐performance photovoltaics due to their high charge mobility and long exciton diffusion length; however, they have not been largely considered for photovoltaics due to the practical difficulty in making a heterojunction between donor and acceptor single crystals. Here, we demonstrate that extended single‐crystalline heterojunctions with a consistent donor‐top and acceptor‐bottom structure throughout the substrate can be simply obtained from a mixed solution of C60 (acceptor) and 3,6‐bis(5‐(4‐n‐butylphenyl)thiophene‐2‐yl)‐2,5‐bis(2‐ethylhexyl)pyrrolo[3,4‐c]pyrrole‐1,4‐dione (donor). 46 photovoltaic devices were studied with the power conversion efficiency of (0.255±0.095) % under 1 sun, which is significantly higher than the previously reported value for a vapor‐grown organic single‐crystalline donor–acceptor heterojunction (0.007 %). As such, this work opens a practical avenue for the study of organic photovoltaics based on single crystals. 相似文献
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Dr. Hai‐Feng Xiang Dr. Stephen Sin‐Yin Chui Prof. V. A. L. Roy Prof. Chi‐Ming Che 《化学:亚洲杂志》2011,6(12):3223-3229
Organic photovoltaic (OPV) cells using metal(II) (Pt, Pd, Cu, and Ni) chelates of 8‐hydroxyquinoline (Hq) or 5,7‐dimethyl‐8‐hydroxy‐quinoline (HMe2q) as an electron donor were fabricated by vacuum deposition. The bis(5,7‐dimethyl‐8‐hydroxyquinolinato)platinum(II) [Pt(Me2q)2]‐based OPVs showed the best performance with an open voltage (VOC) of 0.42 V, a short circuit current density (JSC) of 14.8 mA cm?2, and a maximum power conversion efficiency (ηP) of 2.4 %. The X‐ray single‐crystal structures together with the grazing incidence X‐ray diffraction (GIXRD) data of thin film samples reveal that the peripheral methyl substituent(s) and platinum(II) ion are essential for the high degree of film crystallinity resulting in improved performance of the as‐fabricated field‐effect transistors (FETs) and OPV cells. 相似文献
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Strongly Correlated Alignment of Fluorinated 5,11‐Bis(triethylgermylethynyl)anthradithiophene Crystallites in Solution‐Processed Field‐Effect Transistors 下载免费PDF全文
Dr. Chang‐Hyun Kim Dr. Htay Hlaing Dr. Marcia M. Payne Dr. Kevin G. Yager Prof. Yvan Bonnassieux Prof. Gilles Horowitz Prof. John E. Anthony Prof. Ioannis Kymissis 《Chemphyschem》2014,15(14):2913-2916
The crystallinity of an organic semiconductor film determines the efficiency of charge transport in electronic devices. This report presents a micro‐to‐nanoscale investigation on the crystal growth of fluorinated 5,11‐bis(triethylgermylethynyl)anthradithiophene (diF‐TEG‐ADT) and its implication for the electrical behavior of organic field‐effect transistors (OFETs). diF‐TEG‐ADT exhibits remarkable self‐assembly through spin‐cast preparation, with highly aligned edge‐on stacking creating a fast hole‐conducting channel for OFETs. 相似文献
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Ying Liu Chong‐an Di Dr. Chunyan Du Yunqi Liu Prof. Kun Lu Wenfeng Qiu Dr. Gui Yu Prof. 《Chemistry (Weinheim an der Bergstrasse, Germany)》2010,16(7):2231-2239
A series of fused thiophenes composed of fused α‐oligothiophene units as building blocks, end‐capped with either styrene or 1‐pentyl‐4‐vinylbenzene groups, has been synthesized through Stille coupling reactions. The compounds have been fully characterized by means of 1H NMR spectrometry, high‐resolution mass spectrometry, and elemental analysis. The molecules present a trans–trans configuration between their double bonds, which has been verified and confirmed by Fourier‐transform infrared spectroscopy and single‐crystal X‐ray diffraction analysis. The X‐ray crystal structures showed π–π overlap and sulfur–sulfur interactions between the adjacent molecules. The decomposition temperatures were all found to be above 300 °C, indicating that compounds of this series possess excellent thermal stability. The fact that no phase transition occurs at low temperature indicates that they should be well‐suited for application in devices. Moreover, they possess low HOMO energy levels, based on cyclic voltammetry measurements, and suitable energy gaps, as determined from their thin‐film UV/Vis spectra. Thin‐film X‐ray diffraction analysis and atomic force microscopy revealed high crystallinity on supporting substrates. In addition, as the substrate temperature has a significant influence on the morphology and the degree of crystallinity, the device performance could be optimized by varying the substrate temperature. These materials were found to exhibit optimal field‐effect performance, with a mobility of 0.17 cm2 V?1 s?1 and an on/off ratio of 105, at a substrate temperature of 70 °C. 相似文献
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Naphthalene diimides have received much attention due to their high electron affinities, high electron mobility, and good thermal and oxidative stability, therefore making them promising candidates for a variety of organic electronic applications. However, π‐extended naphthalene diimides with lower HOMO‐LUMO gaps and higher stability have only been developed recently because of the synthetic difficulties. This account describes recent developments in the structures, synthesis, properties, and applications of π‐extended naphthalene diimides, including pure‐carbon and heterocyclic acene diimides, from our research group. 相似文献
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Prof. Dr. Yen‐Ju Cheng Chiu‐Hsiang Chen Tai‐Yen Lin Prof. Dr. Chain‐Shu Hsu 《化学:亚洲杂志》2012,7(4):818-825
We have developed a ladder‐type dithienocyclopentathieno[3,2‐b]thiophene ( DTCTT ) hexacyclic unit in which the central thieno[3,2‐b]thiophene ring was covalently fastened to two adjacent thiophene rings through carbon bridges, thereby forming two connected cyclopentadithiophene ( CPDT ) units in a hexacyclic coplanar structure. This stannylated Sn‐DTCTT building block was copolymerized with three electron‐deficient acceptors, dibromo‐thieno[3,4‐c]pyrrole‐4,6‐dione ( TPD ), dibromo‐benzothiadiazole ( BT ), and dibromo‐phenanthrenequinoxaline ( PQX ), by Stille polymerization, thereby furnishing a new class of alternating donor–acceptor copolymers: PDTCTTTPD , PDTCTTBT , and PDTCTTPQX , respectively. Field‐effect transistors based on PDTCTTPQX and PDTCTTBT yielded high hole mobilities of 0.017 and 0.053 cm2 V?1 s?1, respectively, which are among the highest performances among amorphous donor–acceptor copolymers. A bulk heterojunction solar cell that incorporated PDTCTTTPD with the lower‐lying HOMO energy level delivered a higher Voc value of 0.72 V and a power conversion efficiency (PCE) value of 2.59 %. 相似文献
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《Journal of polymer science. Part A, Polymer chemistry》2018,56(9):1012-1019
Herein, we report the synthesis, characterization, and field‐effect properties of two cross‐conjugated dithienylmethanone (DMO)‐based alternating polymers, namely, PDMO‐S and PDMO‐Se . Both polymers possess high thermal stability, good solubility, and broad absorption spectra. Their electrochemical properties were investigated using cyclic voltammetry, indicating that PDMO‐Se has higher HOMO/LUMO energy levels of −5.49/−3.49 eV than −5.57/−3.58 eV of PDMO‐S . The two polymers exhibited promising charge transport properties with the highest hole mobility of 0.12 cm2 V−1 s−1 for PDMO‐S and 0.025 cm2 V−1 s−1 for PDMO‐Se . AFM and 2D‐GIXRD analyses demonstrated that the PDMO‐S formed lamellar, edge‐on packing thin film with close π‐π stacking. These findings suggest that cross‐conjugated polymers might be potential semiconducting materials for low‐cost and flexible organic electronics. © 2018 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2018 , 56, 1012–1019 相似文献
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Prof. Qichun Zhang Dr. Jinchong Xiao Dr. Zongyou Yin Dr. Hieu M. Duong Fen Qiao Prof. Freddy Boey Prof. Xiao Hu Prof. Hua Zhang Prof. Fred Wudl 《化学:亚洲杂志》2011,6(3):856-862
We report the synthesis and characterization of a novel, stable and blue heteroacene, 2‐methyl‐1,4,6,7,8,9‐hexaphenylbenz(g)isoquinolin‐3(2H)‐one (BIQ 3 ). BIQ 3 , with its relatively small π framework, has an absorption λmax at 620 nm, which is larger than that of pentacene (λmax=582 nm), but BIQ 3 is more stable. The solutions of BIQ 3 are observed without any noticeable photobleaching on the order of days. In the solid state, it is very stable at ambient conditions and can be stored indefinitely. Owing to its pyridone end unit, BIQ 3 can display different resonance structures in different solvents (aprotic and protic) or Lewis acids to give different colors. The attractive stability exhibited by BIQ 3 is very desirable in organic semiconductor devices. Herein, we investigated a simple heterojunction photovoltaic device based on BIQ 3 as an electron donor and [6,6]‐phenyl‐C61 butyric methyl ester as an electron acceptor. Our results show that this type of heteroacene could be a good candidate as a charge‐transport material in organic semiconductor devices. 相似文献
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Synthesis and Properties of Semiconducting Bispyrrolothiophenes for Organic Field‐Effect Transistors 下载免费PDF全文
Crystalann Jones Dr. Damien Boudinet Dr. Yu Xia Mitch Denti Adita Das Dr. Antonio Facchetti Prof. Dr. Tom G. Driver 《Chemistry (Weinheim an der Bergstrasse, Germany)》2014,20(20):5938-5945
A series of new highly soluble bispyrrolothiophenes were synthesized from vinyl azides by using transition‐metal‐catalyzed C?H‐bond functionalization. In addition to modifying the substituents present on the end‐pyrrolothiophene moieties, the arene linker in between the two units was also varied. The solution‐state properties and field‐effect‐transistor (FET) electrical behavior of these bispyrrolothiophenes was compared. Our investigations identified that the optical properties and oxidation potential of our compounds were dominated by the pyrrolothiophene unit with a λmax value of approximately 400 nm and oxidation at approximately 1 V. FET devices constructed with thin films of these bispyrrolothiophenes were also fabricated by means of thin‐film solution processing. One of these compounds, a bispyrrolothiophene linked with benzothiodiazole, exhibits a mobility of approximately 0.3 cm2 V?1 s?1 and the Ion/Ioff value is greater than 106. 相似文献
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《Macromolecular rapid communications》2017,38(10)
The heterocyclic thiazole unit has been extensively used as electron‐deficient building block in π‐conjugated materials over the last decade. Its incorporation into organic semiconducting materials is particularly interesting due to its structural resemblance to the more commonly used thiophene building block, thus allowing the optoelectronic properties of a material to be tuned without significantly perturbing its molecular structure. Here, we discuss the structural differences between thiazole‐ and thiophene‐based organic semiconductors, and the effects on the physical properties of the materials. An overview of thiazole‐based polymers is provided, which have emerged over the past decade for organic electronic applications and it is discussed how the incorporation of thiazole has affected the device performance of organic solar cells and organic field‐effect transistors. Finally, in conclusion, an outlook is presented on how thiazole‐based polymers can be incorporated into all‐electron deficient polymers in order to obtain high‐performance acceptor polymers for use in bulk‐heterojunction solar cells and as organic field‐effect transistors. Computational methods are used to discuss some newly designed acceptor building blocks that have the potential to be polymerized with a fused bithiazole moiety, hence propelling the advancement of air‐stable n‐type organic semiconductors.
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Back Cover: Synthesis and Properties of Semiconducting Bispyrrolothiophenes for Organic Field‐Effect Transistors (Chem. Eur. J. 20/2014) 下载免费PDF全文
Crystalann Jones Dr. Damien Boudinet Dr. Yu Xia Mitch Denti Adita Das Dr. Antonio Facchetti Prof. Dr. Tom G. Driver 《Chemistry (Weinheim an der Bergstrasse, Germany)》2014,20(20):6196-6196
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Weifeng Zhang Congyuan Wei Jianyao Huang Zhihui Chen Liping Wang Gui Yu 《Journal of polymer science. Part A, Polymer chemistry》2017,55(21):3627-3635
In this work, we report the synthesis, characterization, and application of two regioirregular naphthalenediimide (NDI)‐based alternating conjugated polymers, namely P1 and P2 , in which nitrile‐substituted moiety, 2,3‐bis(thiophen‐2‐yl)acrylonitrile and NDI moiety act as donor and acceptor unit, respectively. The two regioirregular polymers possess low‐lying LUMO energy levels of ?3.92 eV for P1 and ?3.96 eV for P2 . Both polymers possess typical dual‐band UV?Vis?NIR absorption profiles of NDI‐based polymers, and show broadened and red‐shifted absorption spectra in the solid state compared with those in solutions. Field‐effect transistor devices with top‐gate bottom‐contact configuration were used to evaluate the polymers' semiconducting properties. The two polymers exhibited promising and air‐stable ambipolar charge transport characteristics. Thin film microstructure investigations (AFM and 2D‐GIXRD) suggest both polymers formed continuous and smooth thin films, and adopted predominantly face‐on molecular packing in the solid state. © 2017 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2017 , 55 , 3627–3635 相似文献
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Xiaoxi Wu Lei Lv Lifang Hu Prof. Qinqin Shi Prof. Aidong Peng Prof. Hui Huang 《Chemphyschem》2019,20(20):2600-2607
Tellurophene-based small molecules and polymers have received great attentions owing to their applications in thin-film transistors, solar cells, and sensors. This article reviews the current progress of the synthesis and applications of tellurophene-based small molecules and polymers. The physicochemical properties and optoelectronic applications of tellurophene-based materials are summarized and discussed. In the end, the challenges and outlook of tellurophene-based materials are presented. 相似文献