Bithiophene-Perfluorobenzene Copolymers

被引：22

作者：

Wang, Yongfeng ^{[1
]}

Watson, Mark D. ^{[1
]}

机构：

[1] Univ Kentucky, Dept Chem, Lexington, KY 40506 USA

来源：

MACROMOLECULES | 2008年 / 41卷 / 22期

基金：

美国国家科学基金会;

关键词：

D O I：

10.1021/ma801400v

中图分类号：

O63 [高分子化学（高聚物）];

学科分类号：

070305 ; 080501 ; 081704 ;

摘要：

A series of copolymers of 3,3 '-dialkylbithiophenes and tetrafluorobenzene units are reported along with non-fluorinated controls. All are characterized by NMR, gel permeation chromatography, differential scanning calorimetry, optical spectroscopy, and wide-angle X-ray diffraction (WAXD). The fluorine substituents enhance backbone planarity, order, and pi-stacking in the solid-state as revealed by optical spectroscopy and WAXD. Peak oxidation potential is also increased by 0.55 V relative to a benchmark polymeric semiconductor, poly(3-hexylthiophene). Head-to-head 3-alkylthiophene linkages do not preclude backbone planarity provided the side chains are not too bulky.

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收藏

页码：8643 / 8647

页数：5

相关论文

共 31 条

[1] X-ray diffraction and theoretical studies for the quantitative assessment of intermolecular arene-perfluoroarene stacking interactions [J].

Bacchi, S ;

Benaglia, M ;

Cozzi, F ;

Demartin, F ;

Filippini, G ;

Gavezzotti, A .

CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (13) :3538-3546

[2] CRYSTAL-STRUCTURE OF 4,4',3'',4'''-TETRAMETHYL-2,2'/5',5'-5'',2'''-TETRATHIOPHENE - A COMPARISON WITH THE CONFORMATION IN SOLUTION [J].

BARBARELLA, G ;

ZAMBIANCHI, M ;

BONGINI, A ;

ANTOLINI, L .

ADVANCED MATERIALS, 1992, 4 (04) :282-285

[3] Solid-state conformation, molecular packing, and electrical and optical properties of processable β-methylated sexithiophenes [J].

Barbarella, G ;

Zambianchi, M ;

Antolini, L ;

Ostoja, P ;

Maccagnani, P ;

Bongini, A ;

Marseglia, EA ;

Tedesco, E ;

Gigli, G ;

Cingolani, R .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (38) :8920-8926

[4] Thiophene and selenophene copolymers incorporating fluorinated phenylene units in the main chain: Synthesis, characterization, and application in organic field-effect transistors [J].

Crouch, DJ ;

Skabara, PJ ;

Lohr, JE ;

McDouall, JJW ;

Heeney, M ;

McCulloch, I ;

Sparrowe, D ;

Shkunov, M ;

Coles, SJ ;

Horton, PN ;

Hursthouse, MB .

CHEMISTRY OF MATERIALS, 2005, 17 (26) :6567-6578

[5] Hexyl-substituted oligothiophenes with a central tetrafluorophenylene unit: crystal engineering of planar structures for p-type organic semiconductors [J].

Crouch, DJ ;

Skabara, PJ ;

Heeney, M ;

McCulloch, I ;

Coles, SJ ;

Hursthouse, MB .

CHEMICAL COMMUNICATIONS, 2005, (11) :1465-1467

[6] Solid-state packing of conjugated oligomers:: from π-stacks to the herringbone structure [J].

Curtis, MD ;

Cao, J ;

Kampf, JW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (13) :4318-4328

[7] High carrier mobility polythiophene thin films: Structure determination by experiment and theory [J].

DeLongchamp, Dean M. ;

Kline, R. Joseph ;

Lin, Eric K. ;

Fischer, Daniel A. ;

Richter, Lee J. ;

Lucas, Leah A. ;

Heeney, Martin ;

McCulloch, Iain ;

Northrup, John E. .

ADVANCED MATERIALS, 2007, 19 (06) :833-+

[8] Low-oxidation-potential conducting polymers derived from 3,4-ethylenedioxythiophene and dialkoxybenzenes [J].

Irvin, JA ;

Schwendeman, I ;

Lee, Y ;

Abboud, KA ;

Reynolds, JR .

JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, 2001, 39 (13) :2164-2178

[9] Synthesis and structure-property relationship of new donor-acceptor-type conjugated monomers and polymers on the basis of thiophene and benzothiadiazole [J].

Jayakannan, M ;

Van Hal, PA ;

Janssen, RAJ .

JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, 2002, 40 (02) :251-261

[10] Critical role of side-chain attachment density on the order and device performance of polythiophenes [J].

Kline, R. Joseph ;

DeLongchamp, Dean M. ;

Fischer, Daniel A. ;

Lin, Eric K. ;

Richter, Lee J. ;

Chabinyc, Michael L. ;

Toney, Michael F. ;

Heeney, Martin ;

McCulloch, Iain .

MACROMOLECULES, 2007, 40 (22) :7960-7965

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