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1.
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
2.
Random multiacceptor poly(2,7‐carbazole) derivatives containing the pentacyclic lactam acceptor unit TPTI for bulk heterojunction solar cells
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Seyma Ekiz Barry C. Thompson 《Journal of polymer science. Part A, Polymer chemistry》2017,55(17):2781-2786
Here, a family of donor/acceptor (D/A) alternating copolymers and random two‐acceptor and three‐acceptor copolymers were synthesized via Suzuki polymerization based on heptadecan‐9‐yl substituted carbazole as a donor and 4,7‐Bis(5‐bromothiophene‐2‐yl)benzo[c][1,2,5]thiadiazole (DTBT), 2,5‐diethylhexyl‐3,6‐bis(5‐bromothiophene‐2‐yl)pyrrolo[3,4‐c]‐pyrrole‐1,4‐dione (DPP) and 2,8‐dibromo‐4,10‐bis(2‐ethylhexyl)thieno[2′,3′:5,6] pyrido[3,4‐g]thieno[3,2‐c]isoquinoline‐5,11(4H,10H)‐dione (TPTI) as acceptors. For the first time, a relatively new electron‐deficient TPTI unit was used as an acceptor in carbazole‐based conjugated polymers. Introduction of the electron‐deficient TPTI unit into the polymer backbone increased the open‐circuit voltage (Voc) of the resulting polymer solar cells up to 0.96 V. PCTPTI and PCDTBT‐TPTI exhibited external quantum efficiencies (EQE) up to 75%. All random two‐acceptor copolymers showed broadened absorption profiles compared to the D/A alternating analogues. In order to further improve the light absorption, a random three‐acceptor copolymer was synthesized for the first time, resulting in the broadest absorption in the range of 350–750 nm. Highest occupied molecular orbital (HOMO) energies and Voc values of the resulting polymers could be successfully tuned by introducing different monomer units into the polymer backbone in different ratios. These results indicate that TPTI is a promising acceptor unit for conjugated polymers and that the random copolymer approach is a successful tool for fine tuning of polymer properties. © 2017 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2017 , 55, 2781–2786 相似文献
3.
Palladium on carbon‐catalyzed direct C—H arylation polycondensation of 3,4‐ethylenedioxythiophene with various dibromoarenes
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Yoshihisa Kojima Shotaro Hayashi Toshio Koizumi 《Journal of polymer science. Part A, Polymer chemistry》2017,55(7):1183-1188
We have demonstrated a direct arylation polycondensation of 3,4‐ethylenedioxythiophene with 2,7‐dibromo‐9,9‐dioctylfluorene using palladium on carbon (Pd/C) as a catalyst. Pd/C is a low‐cost solid‐supported palladium catalyst, giving one of the effective catalytic systems for direct arylation. The Pd/C‐catalyzed direct arylation polycondensation with acetic acid/potassium carbonate in N,N‐dimethylacetamide furnished a high molecular weight π‐conjugated alternating copolymer of EDOT‐fluorene (Mn = 89,300, Mw/Mn = 3.27) in high yield. The polycondensation of EDOT with various dibromoarenes was also achieved, giving EDOT‐carbazole, EDOT‐dialylamine, and EDOT‐bithiophene polymers. Optical and electrochemical properties of the polymers were also discussed. © 2016 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2016 , 55, 1183–1188 相似文献
4.
Grignard condensation routes to 1,3‐disilacyclobutane‐containing cyclolinear polycarbosilanes
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Xinxing Liu Jitendra S. Rathore Geraud Dubois Leonard V. Interrante 《Journal of polymer science. Part A, Polymer chemistry》2017,55(9):1547-1557
Alkylene‐ and arylene‐bridged cyclolinear polycarbosilanes (CLPCS) with 1,3‐disilacyclobutane (DSCB) rings incorporated in the main chain of the polymer were prepared by polycondensation between corresponding di‐functional DSCB derivatives and di‐Grignard reagents. Well‐defined, low molecular weight (Mn = 3–5K; DP = 17–26), hexylene‐ and phenylene‐bridged CLPCS polymers were obtained without appreciable ring opening of the DSCB rings. Large exothermic peaks were observed in the DSC for these CLPCSs, which indicated, along with the IR spectra, that crosslinking occurred on heating to about 250 °C via the ring opening of the embedded, alternating, DSCB rings. Moreover, PB‐CLPCS undergoes photochemically induced crosslinking on UV irradiation to form crosslinked polycarbosilane network films. The spin‐cast, cured, films of these CLPCSs exhibit relatively low dielectric constants and promising thermal and mechanical properties for applications in electronics, for example, directly UV‐photoimprinted low‐k dielectrics. © 2017 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2017 , 55, 1547–1557 相似文献
5.
Yulia A. Piskun Irina V. Vasilenko Sergei V. Kostjuk Kirill V. Zaitsev Galina S. Zaitseva Sergei S. Karlov 《Journal of polymer science. Part A, Polymer chemistry》2010,48(5):1230-1240
The titanium complexes with one ( 1a , 1b , 1c ) and two ( 2a , 2b ) dialkanolamine ligands were used as initiators in the ring‐opening polymerization (ROP) of ε‐caprolactone. Titanocanes 1a and 1b initiated living ROP of ε‐caprolactone affording polymers whose number‐average molecular weights (Mn) increased in direct proportion to monomer conversion (Mn ≤ 30,000 g mol?1) in agreement with calculated values, and were inversely proportional to initiator concentration, while the molecular weight distribution stayed narrow throughout the polymerization (Mw/Mn ≤ 1.2 up to 80% monomer conversion). 1H‐NMR and MALDI‐TOF‐MS studies of the obtained poly(ε‐caprolactone)s revealed the presence of an isopropoxy group originated from the initiator at the polymer termini, indicating that the polymerization takes place exclusively at the Ti–OiPr bond of the catalyst. The higher molecular weight polymers (Mn ≤ 70,000 g mol?1) with reasonable MWD (Mw/Mn ≤ 1.6) were synthesized by living ROP of ε‐caprolactone using spirobititanocanes ( 2a , 2b ) and titanocane 1c as initiators. The latter catalysts, according MALDI‐TOF‐MS data, afford poly(ε‐caprolactone)s with almost equal content of α,ω‐dihydroxyl‐ and α‐hydroxyl‐ω(carboxylic acid)‐terminated chains arising due to monomer insertion into “Ti–O” bond of dialkanolamine ligand and from initiation via traces of water, respectively. © 2010 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 48: 1230–1240, 2010 相似文献
6.
Ren‐Shen Lee Jen‐Ming Yang 《Journal of polymer science. Part A, Polymer chemistry》2005,43(8):1708-1717
A series of novel types of three‐armed poly(trans‐4‐hydroxy‐N‐benzyloxycarbonyl‐L ‐proline)‐block‐poly(ε‐caprolactone) (PHpr‐b‐PCL) copolymers were successfully synthesized via melt block copolymerization of trans‐4‐hydroxy‐N‐benzyloxycarbonyl‐L ‐proline (N‐CBz‐Hpr) and ε‐caprolactone (ε‐CL) with a trifunctional initiator trimethylolpropane (TMP) and stannous octoate (SnOct2) as a catalyst. For the homopolycondensation of N‐CBz‐Hpr with TMP initiator and SnOct2 catalyst, the number‐average molecular weight (Mn) of prepolymer increases from 530 to 3540 g mol?1 with the molar ratio of monomer to initiator (3–30), and the molecular weight distribution (Mw/Mn) is between 1.25 to 1.32. These three‐armed prepolymer PHpr were subsequently block copolymerized with ε‐caprolactone (ε‐CL) in the presence of SnOct2 as a catalyst. The Mn of the copolymer increased from 2240 to 18,840 g mol?1 with the molar ratio (0–60) of ε‐CL to PHpr. These products were characterized by differential scanning calorimetry (DSC), 1H NMR, and gel permeation chromatography. According to DSC, the glass‐transition temperature (Tg) of the three‐armed polymers depended on the molar ratio of monomer/initiator that were added. In vitro degradation of these copolymers was evaluated from weight‐loss measurements and the change of Mn and Mw/Mn. © 2005 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 43: 1708–1717, 2005 相似文献
7.
Yutaka Nanashima Rena Shibata Ryo Miyakoshi Akihiro Yokoyama Tsutomu Yokozawa 《Journal of polymer science. Part A, Polymer chemistry》2012,50(17):3628-3640
Kumada‐Tamao coupling polymerization of 6‐bromo‐3‐chloromagnesio‐2‐(3‐(2‐methoxyethoxy)propyl)pyridine 1 with a Ni catalyst and Suzuki‐Miyaura coupling polymerization of boronic ester monomer 2 , which has the same substituted pyridine structure, with tBu3PPd(o‐tolyl)Br were investigated for the synthesis of a well‐defined n‐type π‐conjugated polymer. We first carried out a model reaction of 2,5‐dibromopyridine with 0.5 equivalent of phenylmagnesium chloride in the presence of Ni(dppp)Cl2 and then observed exclusive formation of 2,5‐diphenylpyridine, indicating that successive coupling reaction took place via intramolecular transfer of Ni(0) catalyst on the pyridine ring. Then, we examined the Kumada‐Tamao polymerization of 1 and found that it proceeded homogeneously to afford soluble, regioregular head‐to‐tail poly(pyridine‐2,5‐diyl), poly(3‐(2‐(2‐(methoxyethoxy)propyl)pyridine) (PMEPPy). However, the molecular weight distribution of the polymers obtained with several Ni and Pd catalysts was very broad, and the matrix‐assisted laser desorption ionization time‐of‐flight mass spectra showed that the polymer had Br/Br and Br/H end groups, implying that the catalyst‐transfer polymerization is accompanied with disproportionation. Suzuki‐Miyaura polymerization of 2 with tBu3PPd(o‐tolyl)Br also afforded PMEPPy with a broad molecular weight distribution, and the tolyl/tolyl‐ended polymer was a major product, again indicating the occurrence of disproportionation. © 2012 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2012 相似文献
8.
Direct arylation polymerization toward ultra‐low bandgap poly(thienoisoindigo‐alt‐diketopyrrolepyrrole) conjugated polymers: The effect of β‐protection on the polymerization and properties of the polymers
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Kai Wang Jing Huang Jieun Ko Wei Lin Leong Mingfeng Wang 《Journal of polymer science. Part A, Polymer chemistry》2017,55(19):3205-3213
Direct arylation polymerization between derivatives of dibromodiketopyrrolopyrrole (DPP) and thienoisoindigo (TIIG) resulted in two π‐conjugated copolymers with average molecular weights up to 24.0 kDa and bandgaps as low as 0.8 eV. The structural analysis of the obtained two polymers revealed well‐defined alternating conjugation backbones without obvious structural defects. The introduction of hexyl‐group in the β‐position of thiophene rings in the DPP units not only reduces the bandgap of conjugated polymer compared to a similar polymer containing bare‐thiophene flanked DPP but also affects polymer morphology in thin films. P‐type charge‐transport characteristics were observed for two polymers in organic field‐effect transistors with comparable hole mobilities. © 2017 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2017 , 55, 3205–3213 相似文献
9.
Yoshimasa Matsumura Hiroki Nishiyama Shinsuke Inagi Ikuyoshi Tomita 《Journal of polymer science. Part A, Polymer chemistry》2019,57(24):2519-2525
The synthesis and unique optoelectronic features of a π‐conjugated polymer containing both thiophene and 1‐phenylphosphole sulfide units (multiple heteroles) in the main chain by the post‐element transformation of a regioregular organometallic polymer possessing titanacyclopentadiene‐2,5‐diyl unit are described. The π‐conjugated polymer containing multiple heteroles was obtained in 73% yield by the simultaneous reaction of the organotitanium polymer with sulfur monochloride and dichlorophenylphosphine (0.6 equiv each), whose number‐average molecular weight (Mn) and the molecular‐weight distribution (Mw/Mn) were estimated to be 11,000 and 3.4, respectively, by the size exclusion chromatography (SEC). The π‐conjugated polymer thus obtained was found to have the high HOMO and the low LUMO energy levels due to the electron‐rich thiophene and electron‐deficient phosphole sulfide units, respectively, as supported by its cyclic voltammetry (CV) analysis. Compared to a mixture of a polymer containing sole thiophene‐unit and that containing sole phosphole sulfide units, the π‐conjugated polymer‐containing multiple heteroles proved to exhibit interesting optical properties. For example, a specific emission peak was observed at 608 nm in the photoluminescence spectrum, which was not observed in the case of the thiophene‐containing polymer, the phosphole‐containing polymer, and their mixture. © 2019 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2019 , 57, 2519–2525 相似文献
10.
Kiyoshi Endo Naoyoshi Hatakeyama 《Journal of polymer science. Part A, Polymer chemistry》2001,39(16):2793-2798
The polymerization of butadiene (Bd) with Co(acac)3 in combination with methylaluminoxane (MAO) was investigated. The polymerization of Bd with Co(acac)3‐MAO catalysts proceeded to give cis‐1,4 polymers (94 – 97%) bearing high molecular weights (40 × 104) with relatively narrow molecular weight distributions (Mw's/Mn's). The molecular weight of the polymers increased linearly with the polymer yield, and the line passed through an original point. The polydispersities of the polymers kept almost constant during reaction time. This indicates that the microstructure and molecular weight of the polymers can be controlled in the polymerization of Bd with the Co(acac)3‐MAO catalyst. The effects of reaction temperature, Bd concentration, and the MAO/Co molar ratio on the cis‐1,4 microstructure and high molecular weight polymer in the polymerization of Bd with Co(acac)3‐MAO catalyst were observed. © 2001 John Wiley & Sons, Inc. J Polym Sci Part A: Polym Chem 39: 2793–2798, 2001 相似文献
11.
Yujuan Nie Bin Zhao Peng Tang Peng Jiang Zongfang Tian Ping Shen Songting Tan 《Journal of polymer science. Part A, Polymer chemistry》2011,49(16):3604-3614
Six alternating conjugated copolymers ( PL1 – PL6 ) of benzo[1,2‐b:4,5‐b′]dithiophene (BDT) and thiophene, containing electron‐withdrawing oxadiazole (OXD), ester, or alkyl as side chains, were synthesized by Stille coupling reaction. The structures of the polymers were confirmed, and their thermal, optical, electrochemical, and photovoltaic properties were investigated. The introduction of conjugated electron‐withdrawing OXD or formate ester side chain benefits to decrease the bandgaps of the polymers and improve the photovoltaic performance due to the low steric hindrance of BDT. Bulk heterojunction polymer solar cells (PSCs) were fabricated based on the blend of the as‐synthesized polymers and the fullerene derivative [6,6]‐phenyl‐C61‐butyric acid methyl ester (PC61BM) in a 1:2 weight ratio. The maximum power conversion efficiency of 2.06% was obtained for PL5 ‐based PSC under the illumination of AM 1.5, 100 mW/cm2. © 2011 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2011 相似文献
12.
Xiaohuan Zhang Zhong Shen Litao Li Sen Zhang Guolin Lu Xiaoyu Huang 《Journal of polymer science. Part A, Polymer chemistry》2007,45(23):5509-5517
A series of well‐defined graft copolymers with a polyallene‐based backbone and polystyrene side chains were synthesized by the combination of living coordination polymerization of 6‐methyl‐1,2‐heptadien‐4‐ol and atom transfer radical polymerization (ATRP) of styrene. Poly(alcohol) with polyallene repeating units were prepared via 6‐methyl‐1,2‐heptadien‐4‐ol by living coordination polymerization initiated by [(η3‐allyl)NiOCOCF3]2 firstly, followed by transforming the pendant hydroxyl groups into halogen‐containing ATRP initiation groups. Grafting‐from route was employed in the following step for the synthesis of the well‐defined graft copolymer: polystyrene was grafted to the backbone via ATRP of styrene. The cleaved polystyrene side chains show a narrow molecular weight distribution (Mw/Mn = 1.06). This kind of graft copolymer is the first example of graft copolymer via allene derivative and styrenic monomer. © 2007 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 45: 5509–5517, 2007 相似文献
13.
Yutaka Miura Atsushi Narumi Soh Matsuya Toshifumi Satoh Qian Duan Harumi Kaga Toyoji Kakuchi 《Journal of polymer science. Part A, Polymer chemistry》2005,43(18):4271-4279
The synthesis of an AB20‐type heteroarm star polymer consisting of a polystyrene arm and 20‐arms of poly(methyl methacrylate) or poly(tert‐butyl acrylate) was carried out using the combination of nitroxide‐mediated polymerization (NMP) and atom transfer radical polymerization (ATRP). The NMP of styrene was carried out using mono‐6‐[4‐(1′‐(2″,2″,6″,6″‐tetramethyl‐1″‐piperidinyloxy)‐ethyl)benzamido]‐β‐cyclodextrin peracetate ( 1 ) to afford end‐functionalized polystyrene with an acetylated β‐cyclodextrin (β‐CyD) unit (prepolymer 2 ) with a number‐average molecular weight (Mn) of 11700 and a polydispersity (Mw/Mn) of 1.17. After deacetylation of prepolymer 2 , the resulting polymer was reacted with 2‐bromoisobutyric anhydride to give end‐functionalized polystyrene with 20(2‐bromoisobutyrol)s β‐CyD, macroinitiator 4 . The copper (I)‐mediated ATRP of methyl methacrylate (MMA) and tert‐butyl acrylate (tBA) was carried out using macroinitiator 4 . The resulting polymers were isolated by SEC fractionation to produce AB20‐type star polymers with a β‐CyD‐core, 5 . The well‐defined structure of 5 with weight‐average molecular weight (Mw)s of 13,500–65,300 and Mw/Mn's of 1.26–1.28 was demonstrated by SEC and light scattering measurements. The arm polymers were separated from 5 by destruction with 28 wt % sodium methoxide in order to analyze the details of their characteristic structure. © 2005 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 43: 4271–4279, 2005 相似文献
14.
Precise synthesis of a series of poly(4‐n‐alkylstyrene)s and their glass transition temperatures
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Satoru Matsushima Atsushi Takano Yoshiaki Takahashi Yushu Matsushita 《Journal of Polymer Science.Polymer Physics》2017,55(9):757-763
Poly(4‐n‐alkylstyrene)s with six kinds of n‐alkyl groups such as methyl, ethyl, propyl, butyl, hexyl, and octyl groups covering wide molecular weight range from around 5 k to over 100 k were precisely synthesized by living anionic polymerizations. It was confirmed that all the polymers obtained have narrow molecular weight distribution, that is, Mw/Mn is all less than 1.1, by SEC. Tgs of all the polymers were estimated by DSC measurements and it turned out to be clear that their molecular weight dependence was well described by the Fox–Flory equations. Furthermore, it is evident that Tg monotonically decreases as a number of carbon atoms of n‐alkyl group is increased, though Tg values are all 20 K or more higher than those reported previously for the same polymer series. This is because backbone mobility increases by introducing longer n‐alkyl side groups with high mobility, while Tg difference in between this work and the previous one may due to the experimental conditions and also to the molecular weight range adopted. © 2017 Wiley Periodicals, Inc. J. Polym. Sci., Part B: Polym. Phys. 2017 , 55, 757–763 相似文献
15.
Xiaojie Zhang Yao Gao Sida Li Xincui Shi Yanhou Geng Fosong Wang 《Journal of polymer science. Part A, Polymer chemistry》2014,52(16):2367-2374
Poly(5,6‐difluoro‐2,1,3‐benzothiadiazole‐alt‐9,9‐dioctylfluorene) was successfully synthesized via direct arylation polycondensation of 5,6‐difluoro‐2,1,3‐benzothiadiazole and 2,7‐dibromo‐9,9‐dioctylfluorene. The reaction conditions were optimized, and a polymer with number‐average molecular weight (Mn) of 41,000 was obtained by using Pd(OAc)2, PtBu2Me‐HBF4, pivalic acid, K2CO3, and toluene as catalyst, ligand, additive, base, and solvent, respectively. The polycondensation was also performed with 5,6‐dioctyloxy‐2,1,3‐benzothiadiazole or 2,1,3‐benzothiadiazole as the comonomer, and the results indicate that the introduction of electron‐withdrawing fluorine atoms at the ortho‐positions to the C? H bonds is essential for the reactivity of the direct arylation. © 2014 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2014 , 52, 2367–2374 相似文献
16.
Min‐Min Shi Dan Deng Lin Chen Jun Ling Lei Fu Xiao‐Lian Hu Hong‐Zheng Chen 《Journal of polymer science. Part A, Polymer chemistry》2011,49(6):1453-1461
A strategy of the fine‐tuning of the degree of intrachain charge transfer and aromaticity of polymer backbone was adopted to design and synthesize new polymers applicable in photovoltaics. Three conjugated polymers P1 , P2 , and P3 were synthesized by alternating the electron‐donating dithieno[3,2‐b:2′3′‐d]pyrrole (D) and three different electron‐accepting (A) segments ( P1 : N‐(2‐ethylhexyl)phthalimide; P2 : 1,4‐diketo‐3,6‐diphenylpyrrolo[3,4‐c]pyrrole; and P3 : thiophene‐3‐hexyl formate) in the polymer main chain. Among the three polymers, P2 possessed the broadest absorption band ranging from 300 to 760 nm, the lowest bandgap (1.63 eV), and enough low HOMO energy level (?5.27 eV) because of the strong intrachain charge transfer from D to A units and the appropriate extent of quinoid state in the main chain of P2 , which was convinced by the theoretical simulation of molecular geometry and front orbits. Photovoltaic study of solar cells based on the blends of P1 – P3 and [6,6]‐phenyl‐C61‐butyric acid methyl ester (PCBM) demonstrated that P2 :PCBM exhibited the best performance: a power conversion efficiency of 1.22% with a high open‐circuit voltage (VOC) of 0.70 V and a large short‐circuit current (ISC) of 5.02 mA/cm2 were achieved. © 2011 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2011 相似文献
17.
Ryousuke Yoshii Atsushi Nagai Kazuo Tanaka Yoshiki Chujo 《Journal of polymer science. Part A, Polymer chemistry》2013,51(8):1726-1733
It is challenging to realize the near‐infrared (NIR) emission with large brightness and sharp spectra from the conjugated polymers. In this study, we demonstrate the strategy for receiving strong and pure NIR emission from polymeric materials using organoboron complexes and the modification after polymerization. A series of NIR emissive conjugated polymers with boron di(iso)indomethenes (BODINs) and fluorene or bithiophene were synthesized by Suzuki–Miyaura coupling reaction. The obtained polymers exhibited high emissions in the range from deep‐red to NIR region (quantum yields: ?PL = 0.40–0.79, full width at half maximum height: Δλ1/2 = 660–940 cm?1, emission maxima: λPL = 686–714 nm). Next, the demethylation of the BODIN‐based polymer with o‐methoxyphenyl groups was carried out. The transformation of the polymer structure quantitatively proceeded via efficient intramolecular crosslinking through the intermediary of the boron atom. Finally, the resulting polymer showed both drastically larger red‐shifted and sharper photoluminescence spectrum than that of the parent polymer with deep‐red emission (?PL = 0.37, Δλ1/2 = 460 cm?1, λPL = 758 nm). © 2013 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2013 相似文献
18.
Jang‐Yong Lee Min‐Hee Choi Ho‐Jun Song Doo‐Kyung Moon 《Journal of polymer science. Part A, Polymer chemistry》2010,48(21):4875-4883
A series of donor‐acceptor low‐bandgap conjugated polymers, that is, HThmBT (m = 3, 6, 9, 12, 15), composed of regioregular 3‐hexylthiophene segments and 2,1,3‐benzothiadiazole units, were synthesized through the Stille coupling polymerization to optimize the π‐conjugation length of the polymer and the intramolecular charge transfer (ICT) effect in the polymer backbone. The polymers had relatively low optical bandgaps ranging from 1.6 to 1.72 eV. Among these polymers, HTh6BT exhibited the best device performance with a power conversion efficiency (PCE) of 1.6%. Moreover, despite being based on thiophene, HTh6BT exhibited a high‐open circuit voltage (VOC) of over 0.8 V because of its low high occupied molecular orbital (HOMO) energy level. These results provided an effective strategy for designing and synthesizing low‐bandgap conjugated polymers with broad absorption ranges and well‐balanced energy levels. © 2010 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2010 相似文献
19.
Asymmetric anionic polymerizations of 7‐(o‐substituted phenyl)‐2,6‐dimethyl‐1,4‐benzoquinone methides: Electrostatic interaction and steric,inductive, and resonance effects of the ortho‐substituent on the optical activity
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Takahiro Uno Shuhei Yamamoto Atsushi Yamane Masataka Kubo Takahito Itoh 《Journal of polymer science. Part A, Polymer chemistry》2017,55(6):1048-1058
7‐(o‐Substituted phenyl)‐2,6‐dimethyl‐1,4‐benzoquinone methides which have an electron‐donating methoxy‐(o‐OMe, 2a ) and methyl‐ (o‐Me, 2b ) substituents or an electron‐withdrawing cyano‐ (o‐CN, 2c ) and trifluoromethyl‐ (o‐CF3, 2d ) substituents at the ortho‐position of the aromatic ring and 7‐(m‐substituted phenyl)‐2,6‐dimethyl‐1,4‐benzoquinone methide with an electron‐withdrawing trifluoromethyl‐ (m‐CF3, 2e ) substituent at the meta‐position of the aromatic ring were synthesized, and their asymmetric anionic polymerizations using the complex of lithium 4‐isopropylphenoxide with (?)‐sparteine were carried out in toluene at 0 °C. The polymers with negative optical activity were obtained for all of five monomers, and their specific rotation values largely changed depending upon the substituents of the monomers. On the basis of the comparison of various substituents effects, it was found that the specific rotation of obtained polymers is significantly affected by the electronic effects such as inductive and resonance effects rather than the steric and electrostatic effects of the substituent. © 2017 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2017 , 55 , 1048–1058 相似文献
20.
Woo Jin Bae Christopher Scilla Volodimyr V. Duzhko Won Ho Jo E. Bryan Coughlin 《Journal of polymer science. Part A, Polymer chemistry》2011,49(15):3260-3271
We report the facile synthesis and characterization of a class of thienothiophene polymers with various lengths of alkyl side chains. A series of 2‐alkylthieno[3,4‐b]thiophene monomers (Ttx) have been synthesized in a two‐step protocol in an overall yield of 28–37%. Poly(2‐alkylthieno[3,4‐b]thiophenes) (PTtx, alkyl: pentyl, hexyl, heptyl, octyl, and tridecyl) were synthesized by oxidative polymerization with FeCl3 or via Grignard metathesis (GRIM) polymerization methods. The polymers are readily soluble in common organic solvents. The polymers synthesized by GRIM polymerization method (PTtx‐G) have narrower molecular weight distribution (?) with lower molecular weight (Mn) than those synthesized by oxidative polymerization (PTtx‐O). The band structures of the polymers with various lengths of alkyl side chains were investigated by UV–vis spectroscopy, cyclic voltammetry, and ultraviolet photoelectron spectroscopy. These low‐bandgap polymers are good candidates for organic transistors, organic light‐emitting diodes, and organic photovoltaic cells. © 2011 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2011 相似文献