Synthesis and Characterization of Soluble Low-Bandgap Oligothiophene-[all]-S,S-dioxides-Based Conjugated Oligomers and Polymers

被引：36

作者：

Amir, Elizabeth ^{[1
,2
]}

Sivanandan, Kulandaivelu ^{[1
,2
]}

Cochran, Justin E. ^{[3
]}

Cowart, John J. ^{[2
,3
]}

Ku, Sung-Yu ^{[1
,2
]}

Seo, Jung Hwa ^{[4
]}

Chabinyc, Michael L. ^{[1
,2
,4
]}

Hawker, Craig J. ^{[1
,2
,3
,4
]}

机构：

[1] Univ Calif Santa Barbara, Mat Res Lab, Santa Barbara, CA 93106 USA

[2] Univ Calif Santa Barbara, Mitsubishi Chem Ctr Adv Mat, Santa Barbara, CA 93106 USA

[3] Univ Calif Santa Barbara, Dept Chem & Biochem, Santa Barbara, CA 93106 USA

[4] Univ Calif Santa Barbara, Dept Mat, Santa Barbara, CA 93106 USA

来源：

JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY | 2011年 / 49卷 / 09期

基金：

美国国家科学基金会;

关键词：

conjugated polymers; crystal structures; oligomers; synthesis; UV-vis spectroscopy; THIOPHENE-BASED MATERIALS; THIN-FILM TRANSISTORS; ELECTRONEGATIVE OLIGOTHIOPHENES; OPTICAL-PROPERTIES; CHARGE-TRANSPORT; HIGHLY-EFFICIENT; DERIVATIVES; COPOLYMERS; OXIDATION; HOF-CENTER-DOT-CH3CN;

D O I：

10.1002/pola.24641

中图分类号：

O63 [高分子化学（高聚物）];

学科分类号：

070305 ; 080501 ; 081704 ;

摘要：

The synthesis and characterization of a new family of soluble oligothiophene-S,S-dioxides and their use as building blocks to form polythiophene-S,S-dioxides via microwave-assisted Stille coupling polymerization are described. Incorporation of the sulfone group into the polythiophene backbone leads to narrowing of the polymer bandgap, and while the energies of both Frontier orbitals in polythiophene-S,S-dioxide are lower with respect to polythiophenes, this tendency is considerably stronger for the lowest unoccupied molecular orbital than for the highest occupied molecular orbital, resulting in greater electron-accepting ability. (C) 2011 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 49: 1933-1941, 2011

引用

页码：1933 / 1941

页数：9

共 52 条

[1] Synthesis of [all]-S,S-dioxide oligothiophenes using HOF•CH3CN [J].

Amir, E ;

Rozen, S .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (45) :7374-7378

[2] Functionalized acenes and heteroacenes for organic electronics [J].

Anthony, John E. .

CHEMICAL REVIEWS, 2006, 106 (12) :5028-5048

[3]

Barbarella G, 1999, ADV MATER, V11, P1375, DOI 10.1002/(SICI)1521-4095(199911)11:16<1375::AID-ADMA1375>3.0.CO

[4]

2-D

[5]

Barbarella G, 1998, ADV MATER, V10, P551, DOI 10.1002/(SICI)1521-4095(199805)10:7<551::AID-ADMA551>3.0.CO

[6]

2-Y

[7] Oligothiophene-S,S-dioxides:: a new class of thiophene-based materials [J].

Barbarella, G ;

Pudova, O ;

Arbizzani, C ;

Mastragostino, M ;

Bongini, A .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (05) :1742-1745

[8]

Beaupré S, 2002, ADV FUNCT MATER, V12, P192, DOI 10.1002/1616-3028(200203)12:3<192::AID-ADFM192>3.0.CO

[9]

2-U

[10] Oligothiophene-S,S-dioxides as a class of electron-acceptor materials for organic photovoltaics [J].

Camaioni, N ;

Ridolfi, G ;

Fattori, V ;

Favaretto, L ;

Barbarella, G .

APPLIED PHYSICS LETTERS, 2004, 84 (11) :1901-1903

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