Synthesis and Characterization of Copolymers Based on Cyclopenta[c]thiophene and Bithiazole and their Transistor Properties

被引:8
作者
Bedi, Anjan [1 ]
Senanayak, Satyaprasad P. [2 ]
Narayan, K. S. [2 ]
Zade, Sanjio S. [1 ]
机构
[1] Indian Inst Sci Educ & Res, Dept Chem Sci, Nadia 741252, W Bengal, India
[2] Jawaharlal Nehru Ctr Adv Sci Res, Chem & Phys Mat Unit, Bangalore 560064, Karnataka, India
关键词
bithiazole; conjugated polymers; copolymers; cyclopenta[c]thiophene; FET; thin film transistors; PHOTOVOLTAIC PROPERTIES; CHARGE-TRANSPORT; POLYMERS; MOBILITY; BENZODITHIOPHENE; OLIGOMERS;
D O I
10.1002/pola.26867
中图分类号
O63 [高分子化学(高聚物)];
学科分类号
070305 ; 080501 ; 081704 ;
摘要
Two new copolymers, P1 and P2, containing 5,5-bis(dodecyloxymethyl)-5,6-dihydro-4H-cyclopenta[c]thiophene (DCPT) or DCPT-based thiophene trimer (as donor) and 4,4-dibutyl-2,2-bithiazole (BTz, as weak acceptor) have been synthesized. To reduce the steric hindrance and enhance the conjugation, the thiophene spacers have been incorporated between DCPT and BTz in P2, which play an important role in maintaining the side chain ordering and -stacking interactions. Both the polymers showed -stacking with similar distances (approximate to 0.37 nm) but with larger extent in P2. Combination of DCPT with BTz has resulted in low lying HOMO levels for the resulting polymers with significant improvement in oxidative stability. P1 and P2 showed p-type mobility of 0.03 and 0.052 cm(2) V-1 s(-1) with current on/off ratio (I-on/I-off) in the order of 10(4) and 10(3), respectively. These differences in characteristics may be attributed to the variation in donor (D)-acceptor (A) property, supramolecular ordering, extent of -stacking, and film microstructure. The polymers were further characterized by GPC, TGA, DSC, PXRD, cyclic voltammetry, and atomic force microscopy. (c) 2013 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2013, 51, 4481-4488
引用
收藏
页码:4481 / 4488
页数:8
相关论文
共 34 条
[1]  
Bard A.J., 2001, ELECTROCHEMICAL METH
[2]   Cyclopenta[c]thiophene oligomers based solution processable D-A copolymers and their application as FET materials [J].
Bedi, Anjan ;
Senanayak, Satyaprasad P. ;
Das, Soumyajit ;
Narayan, K. S. ;
Zade, Sanjio S. .
POLYMER CHEMISTRY, 2012, 3 (06) :1453-1460
[3]   Thieno[3,2-b]thiophene-Diketopyrrolopyrrole-Containing Polymers for High-Performance Organic Field-Effect Transistors and Organic Photovoltaic Devices [J].
Bronstein, Hugo ;
Chen, Zhuoying ;
Ashraf, Rap Shahid ;
Zhang, Weimin ;
Du, Junping ;
Durrant, James R. ;
Tuladhar, Pabitra Shakya ;
Song, Kigook ;
Watkins, Scott E. ;
Geerts, Yves ;
Wienk, Martijn M. ;
Janssen, Rene A. J. ;
Anthopoulos, Thomas ;
Sirringhaus, Henning ;
Heeney, Martin ;
McCulloch, Iain .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (10) :3272-3275
[4]   LIGHT-EMITTING-DIODES BASED ON CONJUGATED POLYMERS [J].
BURROUGHES, JH ;
BRADLEY, DDC ;
BROWN, AR ;
MARKS, RN ;
MACKAY, K ;
FRIEND, RH ;
BURN, PL ;
HOLMES, AB .
NATURE, 1990, 347 (6293) :539-541
[5]   Synthesis, Characterization, and Properties of Regioregular Conjugated Polymers Containing Quaterthiophene and an Acceptor Repeating Units [J].
Chen, Hui ;
Lu, Yong ;
Ong, Teng-Teng ;
Hu, Xiao ;
Ng, Siu-Choon .
JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, 2009, 47 (08) :2163-2171
[6]   ELECTRICAL-CONDUCTIVITY IN DOPED POLYACETYLENE [J].
CHIANG, CK ;
FINCHER, CR ;
PARK, YW ;
HEEGER, AJ ;
SHIRAKAWA, H ;
LOUIS, EJ ;
GAU, SC ;
MACDIARMID, AG .
PHYSICAL REVIEW LETTERS, 1977, 39 (17) :1098-1101
[7]   Bulk Heterojunction Solar Cells Using Thieno[3,4-c]pyrrole-4,6-dione and Dithieno[3,2-b:2′,3′-d]silole Copolymer with a Power Conversion Efficiency of 7.3% [J].
Chu, Ta-Ya ;
Lu, Jianping ;
Beaupre, Serge ;
Zhang, Yanguang ;
Pouliot, Jean-Remi ;
Wakim, Salem ;
Zhou, Jiayun ;
Leclerc, Mario ;
Li, Zhao ;
Ding, Jianfu ;
Tao, Ye .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (12) :4250-4253
[8]   Cyclopenta[c]thiophene-Based D-A Conjugated Copolymers: Effect of Heteroatoms (S, Se, and N) of Benzazole Acceptors on the Properties of Polymers [J].
Das, Soumyajit ;
Pati, Palas Baran ;
Zade, Sanjio S. .
MACROMOLECULES, 2012, 45 (13) :5410-5417
[9]   Synthesis and charge carrier mobility of a solution-processable conjugated copolymer based on cyclopenta[c]thiophene [J].
Das, Soumyajit ;
Senanayak, Satyaprasad P. ;
Bedi, Anjan ;
Narayan, K. S. ;
Zade, Sanjio S. .
POLYMER, 2011, 52 (25) :5780-5787
[10]   Cyclopenta[c]selenophene based cooligomers and their polymers: comparative study with thiophene analogues [J].
Das, Soumyajit ;
Bedi, Anjan ;
Krishna, G. Rama ;
Reddy, C. Malla ;
Zade, Sanjio S. .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (20) :6963-6972