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1.
Tae Wan Lee Nam Su Kang Jae Woong Yu Mai Ha Hoang Kyung Hwan Kim Jung‐Il Jin Dong Hoon Choi 《Journal of polymer science. Part A, Polymer chemistry》2010,48(24):5921-5929
Two conjugated main‐chain polymers consisting of heteroarene‐fused π‐conjuagted donor moiety alternating with 4,7‐bis(5‐bromo‐4‐octylthiophen‐2‐yl)benzo[c][1,2,5]thiadiazole (P1) or 2,5‐bis(5‐bromo‐4‐octylthiophen‐2‐yl) thiazolo[5,4‐d]thiazole (P2) units have been synthesized. They are intrinsically amorphous in nature and do not exhibit crystalline melting temperatures during thermal analysis. The effect of the fused rings on the thermal, optical, electrochemical, charge transport, and photovoltaic properties of these polymers has been investigated. The polymer (P1) containing 4,7‐bis(5‐bromo‐4‐octylthiophen‐2‐yl)benzo[c][1,2,5] thiadiazole has a broad absorption extending from 300 to 600 nm with optical bandgaps as low as 2.02 eV. The HOMO levels (5.42 to 5.29 eV) are more sensitive to the choice of acceptor. The polymers were employed to fabricate organic photovoltaic cells with methanofullerene [6,6]‐phenyl C71‐butyric acid methyl ester (PC71BM). As a result, the polymer solar cell device containing P1 had the best preliminary results with an open‐circuit voltage of 0.61 V, a short‐circuit current density of 6.19 mA/cm2, and a fill factor of 0.32, offering an overall power conversion efficiency of 1.21%. © 2010 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2010 相似文献
2.
Li Zou Yang Fu Xiaobing Yan Xingguo Chen Jingui Qin 《Journal of polymer science. Part A, Polymer chemistry》2008,46(2):702-712
Some linear π‐conjugated polymers containing 2,4,6‐tris(thiophen‐2‐yl)‐1,3,5‐triazine unit were synthesized via Sonogashira or Suzuki reaction for the first time and characterized by IR, NMR, and GPC. Because of the introduction of 2,4,6‐tris(thiophen‐2‐yl)‐1,3,5‐triazine unit into π‐conjugated system, all polymers exhibited good thermal stability with high decomposition temperature. Their optical and electrochemical properties were investigated. Based on the 2,4,6‐tris(thiophen‐2‐yl)‐1,3,5‐triazine unit linked with different aromatic rings, the polymers showed the tunable fluorescence from blue to blue‐green emission with satisfied quantum yield. Cyclic voltammetry measurement indicated that the LUMO and HOMO levels of the polymers could be adjustable through the main‐chain structural modification. All polymers had low LUMO level (?2.86 to ?3.06 eV) due to the high‐electron affinity of triazine unit. © 2007 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 46: 702–712, 2008 相似文献
3.
Jianfu Ding Zhao Li Zhe Cui Gilles P. Robertson Naiheng Song Xiaomei Du Ludmila Scoles 《Journal of polymer science. Part A, Polymer chemistry》2011,49(15):3374-3386
We demonstrated, for the first time, that 3,6‐bis(3‐hexylthien‐2‐yl)‐s‐tetrazine (TTz) with hexyl group at the 3‐position of thiophene rings can be prepared using a modified sulfur‐assisted Pinner synthesis. Although the hexyl group creates large steric hindrance to the tetrazine ring formation reaction, and the reaction under a traditional condition only produces trace amount of the target product, the yield of this reaction under a modified reaction condition using anhydrous hydrazine at 68 °C can reach 65%. Two new copolymers of the resulting TTz and hexyl‐ or 2‐ethylhexyl‐substituted cyclepentadithiophene have been prepared. The polymers show a broader light absorption in film than in solution attributing to the large distribution of effective conjugation length of polymer chain due to the existence of both cis‐ and trans‐orientations of the 3‐hexylthiophene units in the planar polymer chain in solid state. Although the polymers show a narrow band gap and a deep HOMO level, which are desirable for generating an efficient light absorption and a larger open circuit voltage (Voc) of the resulting solar cell devices, the device performance is not as good as expected. It is attributed to the random distribution of the cis‐ and trans‐conformations along the polymer chain. © 2011 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2011. 相似文献
4.
Shanpeng Wen Weidong Cheng Pengfei Li Shiyu Yao Bin Xu Hui Li Yajun Gao Zilong Wang Wenjing Tian 《Journal of polymer science. Part A, Polymer chemistry》2012,50(18):3758-3766
Three donor–acceptor (D–A) 1,3‐di(thien‐2‐yl)thieno [3,4‐c]pyrrole‐4,6‐dione‐based copolymers, poly{9,9‐dioctylfluorene‐2,7‐diyl‐alt‐1,3‐bis(4‐hexylthien‐2‐yl)‐5‐octylthieno[3,4‐c]pyrrole‐4,6‐dione}, poly{N‐(1‐octylnonyl)carbazole‐2,7‐diyl‐alt‐1,3‐bis(4‐hexylthien‐2‐yl)‐5‐octylthieno[3,4‐c]pyrrole‐4,6‐dione}, and poly {4,8‐bis(2‐ethylhexyloxyl) benzo[1,2‐b:3,4‐b′]dithiophene‐alt‐1,3‐bis(4‐hexylthien‐2‐yl)‐5‐octylthieno[3,4‐c] pyrrole‐4,6‐dione} were synthesized by Suzuki or Stille coupling reaction. By changing the donor segment, the bandgaps and energy levels of these copolymers could be finely tuned. Cyclic voltammetric study shows that the highest occupied molecular orbital (HOMO) energy levels of the three copolymers are deep‐lying, which implies that these copolymers have good stability in the air and the relatively low HOMO energy level assures a higher open‐circuit potential when they are used in photovoltaic cells. Bulk‐heterojunction photovoltaic cells were fabricated with these polymers as the donors and PC71BM as the acceptor. The cells based on the three copolymers exhibited power conversion efficiencies of 0.22, 0.74, and 3.11% with large open‐circuit potential of 1.01, 0.99, and 0.90 V under one sun of AM 1.5 solar simulator illumination (100 mW/cm2). © 2012 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2012 相似文献
5.
Vellaiappillai Tamilavan Kyung Hwan Roh Rajalingam Agneeswari Dal Yong Lee Shinuk Cho Youngeup Jin Sung Heum Park Myung Ho Hyun 《Journal of polymer science. Part A, Polymer chemistry》2014,52(24):3564-3574
Pyrrolo[3,4‐c]pyrrole‐1,3(2H,5H)‐dione (DPPD)‐based large band gap polymers, P(BDT‐TDPPDT) and P(BDTT‐TDPPDT), are prepared by copolymerizing electron‐rich 4,8‐bis(2‐ethylhexyloxy)benzo[1,2‐b:4,5‐b′]dithiophene (BDT) or 4,8‐bis(5‐(2‐ethylhexyl)thiophen‐2‐yl)benzo[1,2‐b:4,5‐b′]dithiophene (BDTT) unit with novel electron deficient 2,5‐dioctyl‐4,6‐di(thiophen‐2‐yl)pyrrolo[3,4‐c]pyrrole‐1,3(2H,5H)‐dione (TDPPDT) unit. The absorption bands of polymers P(BDT‐TDPPDT) and P(BDTT‐TDPPDT) cover the region from 300 to 600 nm with an optical band gap of 2.11 eV and 2.04 eV, respectively. The electrochemical study illustrates that the highest occupied/lowest unoccupied molecular orbital energy levels of P(BDT‐TDPPDT) and P(BDTT‐TDPPDT) are ?5.39 eV/?3.28 eV and ?5.44 eV/?3.40 eV, respectively. The single layer polymer solar cell (PSC) fabricated with a device structure of ITO/PEDOT:PSS/P(BDT‐TDPPDT) or P(BDTT‐TDPPDT):PC70BM+DIO/Al offers a maximum power conversion efficiency (PCE) of 6.74% and 6.57%, respectively. The high photovoltaic parameters such as fill factor (~72%), open circuit voltage (Voc, ~0.90 V), incident photon to collected electron efficiency (~76%), and PCE obtained for the PSCs made from polymers P(BDT‐TDPPDT) and P(BDTT‐TDPPDT) make them as promising large band gap polymeric candidates for PSC application. © 2014 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2014 , 52, 3564–3574 相似文献
6.
Shaofeng Liu Weiwei Zuo Shu Zhang Peng Hao Deligeer Wang Wen‐Hua Sun 《Journal of polymer science. Part A, Polymer chemistry》2008,46(10):3411-3423
A series of 6‐(benzimidazol‐2‐yl)‐N‐organylpyridine‐2‐carboxamide were synthesized and transformed into 6‐benzimidazolylpyridine‐2‐carboxylimidate as dianionic tridentate ligands. Bis(2‐(6‐methylpyridin‐2‐yl)‐benzimidazolyl)titanium dichloride ( C1 ) and titanium bis(6‐benzimidazolylpyridine‐2‐carboxylimidate) ( C2 – C8 ) were synthesized in acceptable yields. These complexes were systematically characterized by elemental and NMR analyses. Crystallographic analysis revealed the distorted octahedral geometry around titanium in both complexes C1 and C4 . Using MAO as cocatalyst, all complexes exhibited from good to high catalytic activities for ethylene polymerization. The neutral bis(6‐benzimidazolylpyridine‐2‐carboxylimidate)titanium ( C2 – C8 ) showed high catalytic activities and good stability for prolonged reaction time and elevated reaction temperature; however, C1 showed a short lifetime in catalysis as being observed at very low activity after 5 min. The elevated reaction temperature enhanced the productivity of polyethylenes with low molecular weights, whereas the reaction with higher ethylene pressure resulted in better catalytic activity and resultant polyethylenes with higher molecular weights. At higher ratio of MAO to titanium precursor, the catalytic system generated better activity with producing polyethylenes with lower molecular weights. © 2008 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 46: 3411–3423, 2008 相似文献
7.
《Journal of polymer science. Part A, Polymer chemistry》2018,56(7):689-698
Donor–acceptor (D–A) conjugated polymers bearing non‐covalent configurationally locked backbones have a high potential to be good photovoltaic materials. Since 1,4‐dithienyl‐2,5‐dialkoxybenzene ( TBT ) is a typical moiety possessing intramolecular S…O interactions and thus a restricted planar configuration, it was used in this work as an electron‐donating unit to combine with the following electron‐accepting units: 3‐fluorothieno[3,4‐b]thiophene ( TFT ), thieno‐[3,4‐c]pyrrole‐4,6‐dione ( TPD ), and diketopyrrolopyrrole ( DPP ) for the construction of such D–A conjugated polymers. Therefore, the so‐designed three polymers, PTBTTFT , PTBTTPD , and PTBTDPP , were synthesized and investigated on their basic optoelectronic properties in detail. Moreover, using [6,6]‐phenyl‐C71‐butyric acid methyl ester (PC71BM) as acceptor material, polymer solar cells (PSCs) were fabricated for studying photovoltaic performances of these polymers. It was found that the optimized PTBTTPD cell gave the best performance with a power conversion efficiency (PCE) of 4.49%, while that of PTBTTFT displayed the poorest one (PCE = 1.96%). The good photovoltaic behaviors of PTBTTPD come from its lowest‐lying energy level of the highest occupied molecular orbital (HOMO) among the three polymers, and good hole mobility and favorable morphology for its PC71BM‐blended film. Although PTBTDPP displayed the widest absorption spectrum, the largest hole mobility, and regular chain packing structure when blended with PC71BM, its unmatched HOMO energy level and disfavored blend film morphology finally limited its solar cell performance to a moderate level (PCE: 3.91%). © 2018 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2018 , 56, 689–698 相似文献
8.
Joo Bin Lee Kyung Hwan Kim Chang Seop Hong Dong Hoon Choi 《Journal of polymer science. Part A, Polymer chemistry》2012,50(14):2809-2818
New diketopyrrolopyrrole (DPP)‐containing amorphous conjugated polymers, such as poly(3‐(5‐((9,10‐bis((4‐hexylphenyl)ethynyl)‐6‐(prop‐1‐ynyl)anthracen‐2‐yl)ethynyl) thiophen‐2‐yl)‐5‐(2‐hexyldecyl)‐2‐(2‐octyldodecyl)‐6‐(thiophen‐2‐yl)pyrrolo[3,4‐c]pyrrole‐1,4(2H,5H)‐dione) ( 4 ), and poly(3‐(5‐((2,6‐bis((4‐hexylphenyl)ethynyl)‐10‐(prop‐1‐ynyl)anthracen‐9‐yl)ethynyl)thiophen‐2‐yl)‐2,5‐bis(2‐octyldodecyl)‐6‐(thio phen‐2‐yl)pyrrolo[3,4‐c]pyrrole‐1,4(2H,5H)‐dione) ( 7 ), were successfully synthesized via Sonogashira coupling reactions under microwave conditions. Copolymer 7 , incorporating a DPP moiety at the 9,10‐position of the anthracene ring through a triple bond, showed a much lower bandgap energy (Eg = 1.81 eV) than copolymer 4 (Eg = 2.13 eV). Tuning of the molecular frontier orbital energies was achieved by only changing the anchoring position of dithiophenyl‐DPP from the 2,6‐ to the 9,10‐position in the anthracene ring. Because of the donor–acceptor (D–A) interaction and the two‐dimensional planar structure of the X‐shaped donor monomer, the resulting polymers showed good interchain π?π stacking in the thin‐film state, despite being amorphous polymers. When the newly synthesized polymer 7 was used as a semiconductor material in an organic thin‐film transistor, the best mobility of up to 0.12 cm2 V?1 s?1 (Ion/off = ~ 4.4 × 106) was observed, which is one of the highest values recorded for amorphous polymer films reported to date. © 2012 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2012 相似文献
9.
Mukhamed L. Keshtov Sergei A. Kuklin Igor O. Konstantinov Ilya E. Ostapov Dmitrii Y. Godovsky Elena E. Makhaeva Zhiyuan Xie Ganesh D. Sharma 《Journal of polymer science. Part A, Polymer chemistry》2019,57(13):1478-1485
A series of novel donor–acceptor (D–A) random conjugated terpolymers P2‐P4 along with the homopolymers P1 (BDT‐DPP) and P5 (BDT‐BTDQ) were designed and synthesized by copolymerizing a benzo[1,2‐b:4,5‐b]dithiophene (BDT) donor with an electron‐deficient diketopyrrolo[3,4‐c]pyrrole (DPP) unit and a benzothiadiazolo[3,4‐e]quinoxaline (BTDQ) moieties of different electron‐withdrawing strengths, and the resultant terpolymers showed broad absorption profile ranging from 300 to 1200 nm. The HOMO levels of the polymers were adjusted from ?5.23 to ?5.11 eV, and the optical bandgaps were controlled from 1.32 to 1.13 eV by changing the molar ratio of DPP and BTDQ acceptors. These terpolymers were used as a donor along with PC71BM as an acceptor for the creation of polymer solar cells, and the performance was optimized via variable the donor to acceptor ratio and solvent vapor annealing. The polymer solar cells made from the random terpolymer P3 showed the highest overall power conversion efficiency of (9.27%), which is higher than that for the corresponding homo‐polymers counterparts, that is, P1 (7.27%) and P5 (7.68%). The results demonstrate that the designing of random D‐A1‐D‐A2 terpolymers may be the best approach for efficient polymer solar cells. © 2019 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2019, 57, 1478–1485 相似文献
10.
Incorporation of different conjugated linkers into low band gap polymers based on 5,6‐Bis(octyloxy)‐2,1,3 benzooxadiazole for tuning optoelectronic properties
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Seza Goker Gonul Hizalan Seda Kutkan Yasemin Arslan Udum Ali Cirpan Levent Toppare 《Journal of polymer science. Part A, Polymer chemistry》2016,54(16):2459-2467
Four new 2,1,3‐benzooxadiazole‐based donor–acceptor conjugated polymers, namely poly{9‐(9‐heptadecanyl)‐9H‐carbazole‐alt‐5,6‐bis(octyloxy)‐4,7‐di(selenophen‐2‐yl)benzo[c][1,2,5]oxadiazole)}(PSBSC), poly{9‐(9‐heptadecanyl)‐9H‐carbazole‐alt‐5,6‐bis(octyloxy)‐4,7‐di(furan‐2‐yl)benzo[c][1,2,5]oxadiazole)}(PFBFC), poly{9,9‐dioctyl‐9H‐fluorene‐alt‐5,6‐bis(octyloxy)‐4,7‐di(selenophen‐2‐yl)benzo[c][1,2,5]oxadiazole)}(PSBSFL), and poly{9,9‐dioctyl‐9H‐fluorene‐alt‐5,6‐bis(octyloxy)‐4,7‐di(furan‐2‐yl)benzo[c][1,2,5]oxadiazole)}(PFBFFL), were synthesized via Stille polycondensation reaction. All polymers were found to be soluble in common organic solvents such as chloroform, tetrahydrofuran, and chlorobenzene. Their structures were verified by 1H‐NMR and the molecular weights were determined by gel permeation chromatography (GPC). The polymer films exhibited broad absorption bands. Among all polymers, photovoltaic cells based on the device structure of ITO/PEDOT:PSS/PSBSC:PC71BM(1:3, w/w)/LiF/Al revealed an open‐circuit voltage of 0.62 V, a short circuit current of 7.63 mA cm?2 and a power conversion efficiency of 1.89%. This work demonstrates a good example for tuning absorption range, energy level, and photovoltaic properties of the polymers with different spacers and donor units can offer a simple and effective method to improve the efficiency of PSCs. © 2016 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2016 , 54, 2459–2467 相似文献
11.
Effect of hexyl substituent groups on photophysical and electrochemical properties of the poly[(9,9‐Dioctyluorene)−2,7‐diyl‐alt‐(4,7‐bis (3‐Hexylthien‐5‐Yl)−2,1,3‐Benzothiadiazole)−2′,2″‐diyl]
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Daniel J. da Silva Herick G. Takimoto Karine C. C. Weber dos Santos Jarem R. Garcia Debora T. Balogh Shu Hui Wang 《Journal of Polymer Science.Polymer Physics》2016,54(19):1975-1982
The effect of the presence of hexyl group in thiophene on the photophysical and electrochemical properties of poly[(9,9‐dioctyluorene)?2,7‐diyl‐alt‐(4,7‐bis(3‐hexylthien‐5‐yl)?2,1,3‐benzothiadiazole)?2′,2″‐diyl] (F8TBT) is investigated. The copolymers present electron donor–acceptor architecture and are synthesized by Suzuki coupling reaction. The UV/Vis spectra show absorption maximum in the wavelength range of blue and orange, which are associated with different segments of the polymer backbone. Addition of hexyl substituent groups has a positive effect on the molar absorptivity and increases the emission and absorption intensities due to fluorene and thiophene‐benzothiadiazole‐thiophene (TBT) units, although an increment in the bandgap is observed. Cyclic voltammetry study of the polymer films reveal irreversible reduction and oxidation processes of the TBT units in the polymer chain and the HOMO and LUMO energy levels suggest ambipolar character for the polymers, while the electrochemical bandgaps are consistent with the absorbance measurements. © 2016 Wiley Periodicals, Inc. J. Polym. Sci., Part B: Polym. Phys. 2016 , 54, 1975–1982 相似文献
12.
Shinn‐Horng Chen Yun Chen 《Journal of polymer science. Part A, Polymer chemistry》2004,42(23):5900-5910
To investigate the effect of trifluoromethyl groups in enhancing electron affinity of aromatic oxadiazole and triazole chromophores, we prepared four new copoly(aryl ether)s ( P1 – P4 ) consisting of bis(3‐(trifluoromethyl) phenyl)‐1,3,4‐oxadiazole (ETO) or bis(3‐(trifluoromethyl)phenyl)‐4‐(4‐hexyloxyphenyl)‐4H‐1,2,4‐triazole (ETT) segments and hole‐transporting segments [2,5‐distyrylbenzene (HTB) or bis(styryl)fluorine (HTF)]. Molecular spectra (absorption and photoluminescence) and cyclic voltammetry were used to investigate their optical and electrochemical properties. The emissions of P1 – P4 are dominated by the hole‐transporting fluorophores with longer emissive wavelengths around 442–453 nm via efficient excitation energy transfer. The highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) energy levels of P1 – P4 , estimated from electrochemical data, are ?5.15, ?5.18, ?5.30, ?5.27, ?3.39, ?3.49, ?3.36, and ?3.48 eV, respectively. The LUMO levels of ETO and ETT segments are significantly reduced to ?3.39~?3.36 eV and ?3.48~?3.49 eV, respectively, as compared with ?2.45 eV of P5 containing a 2,5‐diphenyl‐1,3,4‐oxadiazole segment. Moreover, electron and hole affinity can be enhanced simultaneously by introducing isolated hole‐ and electron‐transporting segments in the backbone. © 2004 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 42: 5900–5910, 2004 相似文献
13.
Xiaofeng Xu Ping Cai Yong Lu Ng Siu Choon Junwu Chen Xiao Hu Beng S. Ong 《Journal of polymer science. Part A, Polymer chemistry》2013,51(2):424-434
A novel class of thieno[3,2‐b]thiophene (TT) and isoindigo based copolymers were synthesized and evaluated as electron donor and hole transport materials in bulk‐heterojunction polymer solar cells (BHJ PSCs). These π‐conjugated donor‐acceptor polymers were derived from fused TT and isoindigo structures bridged by thiophene units. The band‐gaps and the highest occupied molecular orbital (HOMO) levels of the polymers were tuned using different conjugating lengths of thiophene units on the main chains, providing band‐gaps from 1.55 to 1.91 eV and HOMO levels from ?5.34 to ?5.71 eV, respectively. The corresponding lowest unoccupied molecular orbital (LUMO) levels were appropriately adjusted with the isoindigo units. Conventional BHJ PSCs (ITO/PEDOT:PSS/active layer/interlayer/Al) with an active layer composed of the polymer and PC71BM were fabricated for evaluation. Power conversion efficiency from a low of 1.25% to a high of 4.69% were achieved with the best performing device provided by the D?π?A polymer with a relatively board absorption spectrum, high absorption coefficient, and more uniform blend morphology. These results demonstrate the potential of this class of thieno[3,2‐b]thiophene‐isoindigo‐based polymers as efficient electron donor and hole transport polymers for BHJ PSCs. © 2012 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2013 相似文献
14.
Da Seul Yang Kyung Hwan Kim Min Ju Cho Jung‐Il Jin Dong Hoon Choi 《Journal of polymer science. Part A, Polymer chemistry》2013,51(6):1457-1467
New diketopyrrolopyrrole (DPP)‐containing conjugated polymers such as poly(2,5‐bis(2‐octyldodecyl)‐3‐(5‐(pyren‐1‐yl)thiophen‐2‐yl)‐6‐(thiophen‐2‐yl)pyrrolo[3,4‐c]pyrrole‐1,4(2H,5H)‐dione) (P(DTDPP‐alt‐(1,6)PY)) and poly(2,5‐bis(2‐octyldodecyl)‐3‐(5‐(pyren‐2‐yl)thiophen‐2‐yl)‐6‐(thiophen‐2‐yl)pyrrolo[3,4‐c]pyrrole‐1,4(2H,5H)‐dione) (P(DTDPP‐alt‐(2,7)PY)) were successfully synthesized via Suzuki coupling reactions under Pd(0)‐catalyzed conditions. P(DTDPP‐alt‐(2,7)PY), incorporating 2,5‐bis(2‐octyldodecyl)‐3,6‐di(thiophen‐2‐yl)pyrrolo[3,4‐c]pyrrole‐1,4(2H,5H)‐dione (DTDPP) at the 2,7‐position of a pyrene ring showed a lower band‐gap energy (E. = 1.65 eV) than the 1,6‐substituted analog, P(DTDPP‐alt‐(1,6)PY) (E = 1.71 eV). The energies of the molecular frontier orbitals of the substituted polymers were successfully tuned by changing the anchoring position of DTDPP from the 1,6‐ to the 2,7‐position of the pyrene ring. An organic thin‐film transistor fabricated using the newly synthesized P(DTDPP‐alt‐(2,7)PY), as a semiconductor material exhibited a maximum mobility of up to 0.23 cm2 V?1 s?1 (Ion/off ~ 106), which was much larger than that obtained using P(DTDPP‐alt‐(1,6)PY). This distinction is attributed to morphological differences in the solid state arising from differences between the geometrical configurations of DTDPP and the pyrene ring. In addition, the organic phototransistor devices made of P(DTDPP‐alt‐(2,7)PY) showed interesting photoinduced enhancement of drain current when irradiating the excitation light whose intensity is very small. Based on the photoinduced effect on IDS, photocontrolled memory could be realized under the variation of gate voltages. © 2013 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2013 相似文献
15.
《Acta Crystallographica. Section C, Structural Chemistry》2018,74(2):171-176
A dimerized 1,3‐diazaazulene derivative, namely 1,4‐bis(1,3‐diazaazulen‐2‐yl)benzene [or 2,2′‐(1,4‐phenylene)bis(1,3‐diazaazulene)], C22H14N4, (I), has been synthesized successfully through the condensation reaction between 2‐methoxytropone and benzene‐1,4‐dicarboximidamide hydrochloride, and was characterized by 1H NMR and 13C NMR spectroscopies, and ESI–MS. X‐ray diffraction analysis reveals that (I) has a nearly planar structure with good π‐electron delocalization, indicating that it might serve as a π building block. The crystal belongs to the monoclinic system. One‐dimensional chains were formed along the a axis through π–π interactions and adjacent chains are stabilized by C—H…N interactions, forming a three‐dimensional architecture. The solid emission of (I) in the crystalline form exhibited a 170 nm red shift compared with that in the solution state. The observed optical bandgap for (I) is 3.22 eV and a cyclic voltammetry experiment confirmed the energy levels of the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO). The calculated bandgap for (I) is 3.37 eV, which is very close to the experimental result. In addition, the polarizability and hyperpolarizability of (I) were appraised for its further application in second‐order nonlinear optical materials. 相似文献
16.
Achala Bhuwalka Monique D. Ewan Moneim Elshobaki Jared F. Mike Brian Tlach Sumit Chaudhary Malika Jeffries‐EL 《Journal of polymer science. Part A, Polymer chemistry》2016,54(3):316-324
In an effort to design efficient low‐cost polymers for use in organic photovoltaic cells the easily prepared donor–acceptor–donor triad of a either cis‐benzobisoxazole, trans‐benzobisoxazole or trans‐benzobisthiazole flanked by two thiophene rings was combined with the electron‐rich 4,8‐bis(5‐(2‐ethylhexyl)‐thien‐2‐yl)‐benzo[1,2‐b:4,5‐b′]dithiophene. The electrochemical, optical, morphological, charge transport, and photovoltaic properties of the resulting terpolymers were investigated. Although the polymers differed in the arrangement and/or nature of the chalcogens, they all had similar highest occupied molecular orbital energy levels (?5.2 to ?5.3 eV) and optical band gaps (2.1–2.2 eV). However, the lowest unoccupied molecular orbital energy levels ranged from ?3.1 to ?3.5 eV. When the polymers were used as electron donors in bulk heterojunction photovoltaic devices with PC71BM ([6,6]‐phenyl C71‐butyric acid methyl ester) as the acceptor, the trans‐benzobisoxazole polymer had the best performance with a power conversion efficiency of 2.8%. © 2015 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2016 , 54, 316–324 相似文献
17.
M. L. Keshtov S. A. Kuklin D. Y. Godovsky A. R. Khokhlov R. Kurchania F. C. Chen Emmanuel N. Koukaras G. D. Sharma 《Journal of polymer science. Part A, Polymer chemistry》2016,54(1):155-168
A novel D–A1–D–A2 copolymer denoted as P1 containing two electron withdrawing units based on benzothiadiazole (BT) and 9‐(2‐octyldodecyl)?8H‐pyrrolo[3,4‐b] bisthieno[2,3‐f:3′,2′‐h]quinoxaline‐8,10(9H)–dione (PTQD) units was synthesized and characterized. The resulting copolymer exhibits a broad‐absorption spectrum, relatively deep lying HOMO energy level (?5.44 eV) and narrow optical bandgap (1.50 eV). Bulk heterojunction (BHJ) polymer solar cells (PSCs) based on P1 as donor and PC71BM as acceptor with optimized donor to acceptor weight ratio of 1:2 and processed with DIO/CB solvent showed good photovoltaic performance with power conversion efficiency of 6.21% which is higher than that of the device processed without solvent additive (4.40%). The absorption and morphology investigations of the active layers indicated that structural and morphological changes were induced by the solvent additive. This higher power conversion efficiency could be mainly attributed to the absorption enhancement and improved charge transported in the active layer induced by the better nanoscale morphology of the active layer. This study demonstrated that a copolymer with two different acceptor moieties in the backbone may be promising candidate as donor copolymer for solution processed BHJ PSCs. © 2015 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2016 , 54, 155–168 相似文献
18.
Koji Takagi Hyunho Joo Yusuke Yamashita Eiki Kawagita Chikako Torii 《Journal of polymer science. Part A, Polymer chemistry》2011,49(18):4013-4020
2,5‐Dibromo‐3‐(6′‐hexylpyridine‐2′‐yl)thiophene ( DBPyTh ) was synthesized by the Suzuki coupling reaction between two aromatic compounds followed by the bromination. The Grignard metathesis reaction of DBPyTh with isopropylmagnesium chloride proceeded in 85% conversion and the regioselective halogen–metal exchange at the 2‐position was confirmed. Namely, 5‐bromo‐2‐chloromagnesio‐3‐(6′‐hexylpyridine‐2′‐yl)thiophene and 2‐bromo‐5‐chloromagnesio‐3‐(6′‐hexylpyridine‐2′‐yl)thiophene were generated in 90:10 molar ratio. Subsequently, the Kumada coupling polymerization was carried out using 1,3‐bis(diphenylphosphinopropane)nickel(II) dichloride to obtain poly(3‐(6′‐hexylpyridine‐2′‐yl)thiophene) ( PolyPyTh ). The polymer molecular weight could be roughly controlled by the catalyst concentration and the molecular weight distribution ranged from 1.25 to 1.80. The gas chromatograph analysis indicated that 5‐bromo‐2‐chloromagnesio‐3‐(6′‐hexylpyridine‐2′‐yl)thiophene was preferentially polymerized in 90% conversion and the percentage of the head‐to‐tail content (regioregularity) was calculated to be 96%. The matrix‐assisted laser desorption/ionization time‐of‐fright mass spectrum indicated that both polymer chain ends were substituted with the hydrogen atom. The absorption maxima of polymer in CHCl3 and thin film were observed at 447 and 457 nm, respectively, which were blue‐shifted compared with poly(3‐(4′‐octylphenyl)thiophene). From the CV measurement of the polymer thin film, highest occupied molecular orbital (HOMO) (?5.31 eV) and lowest unoccupied molecular orbital (LUMO) (?3.76 eV) energy levels were calculated from the oxidation and reduction onset potentials, respectively, and the electrochemical band gap energy was determined to be 1.62 eV. © 2011 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2011 相似文献
19.
Shiao‐Wen Hwang Shinn‐Horng Chen Yun Chen 《Journal of polymer science. Part A, Polymer chemistry》2002,40(14):2215-2224
Four novel poly(aryl ether)s ( P1 – P4 ) consisting of alternate isolated electron‐transporting (3,3″′‐bis‐trifluoromethyl‐p‐quaterphenyl for P1 , P3 or 3,3″′‐dicyano‐p‐quaterphenyl for P2 , P4 ) and hole‐transporting fluorophores [N‐(2‐ethylhexyl)‐3,6‐bis(styryl)carbazole for P1 , P2 or 9,9‐dihexyl‐2,7‐bis(styryl)fluorene for P3 , P4 ] were synthesized and characterized. These poly(aryl ether)s can be dissolved in organic solvents and exhibited good thermal stability with 5% weight‐loss temperature above 500 °C in nitrogen atmosphere. The photoluminescent (PL) spectra of the films of these polymers showed maximum peaks at around 442–452 nm. The PL spectral results revealed that the emission of polymers was dominated by the fluorophores with longer emissive wavelength via the energy transfer from p‐quaterphenyl to 3,6‐bis(styryl)carbazole or 2,7‐bis(styryl)fluorene segments. Therefore, the p‐quaterphenyl segments function only as the electron‐transporting/hole‐blocking units in these polymers, and the other segments are the emissive centers and hole‐transporting units. The highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital energy levels of these polymers were measured by cyclic voltammetry. The electron‐donating nitrogen atom on carbazole resulted in the higher HOMO energy levels of P1 and P2 than those of P3 and P4 . The single‐layer light‐emitting diodes (LED) of Al/poly(aryl ether)s ( P1 – P4 )/ITO glass were fabricated. P1 , P2 , and P4 revealed blue electroluminescence, but P3 emitted yellow light as a result of the excimer emission. © 2002 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 40: 2215–2224, 2002 相似文献
20.
Věra Cimrová Ivan Kmínek Petra Pavlačková Drahomír Výprachtický 《Journal of polymer science. Part A, Polymer chemistry》2011,49(15):3426-3436
Two new low‐bandgap alternating copolymers (CEHTF and CEHTP) consisting of 4,6‐bis(3′‐(2‐ethylhexyl)thien‐2′‐yl)thieno[3,4‐c][1,2,5] thiadiazole and 9,9‐bis(2‐ethylhexyl)fluorene or 2,5‐bis(isopentyloxy)benzene were synthesized by Suzuki coupling reaction of corresponding comonomers. Their optical, electrochemical, and photovoltaic (PV) properties were studied and are reported. Both the copolymers exhibited long‐wavelength absorption covering the whole visible spectral region, which is in CEHTP thin films extended up to near infrared region, ambipolar redox properties, and electrochromism. High‐electron affinities and low‐optical bandgap values, 1.37 and 1.15 eV, were determined for CEHTF and CEHTP, respectively. PV devices with bulk heterojunction made of blends of copolymers and fullerene derivative [6,6]‐phenyl‐C61‐butyric acid methyl ester ([60]PCBM) were prepared and characterized. Effects of intramolecular charge transfer strength and side‐chain nature and length on photophysical properties are discussed. © 2011 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2011 相似文献