Synthetic studies of extraordinarily long oligothiophenes

被引：11

作者：

Otsubo, T ^{[1
]}

Aso, Y ^{[1
]}

Takimiya, K ^{[1
]}

Nakanishi, H ^{[1
]}

Sumi, N ^{[1
]}

机构：

[1] Hiroshima Univ, Grad Sch Engn, Dept Appl Chem, Higashihiroshima 7398527, Japan

来源：

SYNTHETIC METALS | 2003年 / 133卷

关键词：

oligothiophenes; nanoscale molecules; mono-disperse polymers; effective conjugation length;

D O I：

10.1016/S0379-6779(02)00376-4

中图分类号：

T [工业技术];

学科分类号：

08 ;

摘要：

This paper describes synthetic approaches to extraordinarily long oligothiophenes, which correspond to mono-disperse polymers. The most successful approach is a combination of a random coupling reaction of mono- and diethynylsexithiophenes and a subsequent sodium sulfide-induced cyclization reaction of the diacetylene parts to thiophene rings, forming a series of long oligothiophenes Oct-nT up to the 48-mer. The systematic study of the Oct-nT series reveals that the effective conjugation length of conjugated polythiophenes extends to around 20 thiophene units. (C) 2002 Elsevier Science B.V. All rights reserved.

引用

页码：325 / 328

页数：4

共 15 条

[1] OLIGOTHIOPHENES - YET LONGER - SYNTHESIS, CHARACTERIZATION, AND SCANNING-TUNNELING-MICROSCOPY IMAGES OF HOMOLOGOUS, ISOMERICALLY PURE OLIGO(ALKYLTHIOPHENE)S [J].

BAUERLE, P ;

FISCHER, T ;

BIDLINGMEIER, B ;

STABEL, A ;

RABE, JP .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1995, 34 (03) :303-307

[2]

Bauerle P, 1999, HDB OLIGO POLYTHIOPH

[3] Growth and structural characterization of the quasi-2D single crystal of alpha-octithiophene [J].

Fichou, D ;

Bachet, B ;

Demanze, F ;

Billy, I ;

Horowitz, G ;

Garnier, F .

ADVANCED MATERIALS, 1996, 8 (06) :500-+

[4] HOMOCOUPLING OF ARYL HALIDES USING NICKEL(II) COMPLEX AND ZINC IN THE PRESENCE OF ET4NI - AN EFFICIENT METHOD FOR THE SYNTHESIS OF BIARYLS AND BIPYRIDINES [J].

IYODA, M ;

OTSUKA, H ;

SATO, K ;

NISATO, N ;

ODA, M .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1990, 63 (01) :80-87

[5] SYNTHESIS OF ALPHA-THIOPHENE OLIGOMERS VIA 1,3-BUTADIYNES [J].

KAGAN, J ;

ARORA, SK .

JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (23) :4317-4320

[6] Effective conjugation length and UV/vis spectra of oligomers [J].

Meier, H ;

Stalmach, U ;

Kolshorn, H .

ACTA POLYMERICA, 1997, 48 (09) :379-384

[7] Synthesis and properties of the longest oligothiophenes: The icosamer and heptacosamer [J].

Nakanishi, H ;

Sumi, N ;

Aso, Y ;

Otsubo, T .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (24) :8632-8633

[8] The longest class of oligothiophenes [J].

Nakanishi, H ;

Aso, Y ;

Otsubo, T .

SYNTHETIC METALS, 1999, 101 (1-3) :604-605

[9]

NAKANISHI H, UNPUB

[10] Synthesis, optical, and conductive properties of long oligothiophenes and their utilization as molecular wires [J].

Otsubo, T ;

Aso, Y ;

Takimiya, K .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2001, 74 (10) :1789-1801

← 1 2 →