Non-symmetrical oligothiophenes with 'incompatible' substituents

被引：17

作者：

Didier, Delphine ^{[1
]}

Sergeyev, Sergey ^{[1
]}

Geerts, Yves Henri ^{[1
]}

机构：

[1] Univ Libre Bruxelles, Lab Chim Polymeres, B-1050 Brussels, Belgium

来源：

TETRAHEDRON | 2007年 / 63卷 / 04期

关键词：

liquid crystals; oligothiophenes; perfluoroalkylation; cross-coupling;

D O I：

10.1016/j.tet.2006.11.029

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The syntheses of oligothiophenes 1 and 2 comprising two different types of peripheral substituents, namely alkyl and perfluoroalkyl, is reported. The key synthetic step is the Pd-catalyzed cross-coupling of perfluoroalkylated bromide 3 with an appropriate boronate. This molecular design is expected to promote unusual two-layer packing, which is of interest for application in electronic devices. Quaterthiophene 1 forms smectic mesophase, though in the narrow temperature range, and is suitable for the fabrication of thin films by solution processing methods. (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：941 / 946

页数：6

共 25 条

[1] SELECTIVE SYNTHESIS OF ALPHA-SUBSTITUTED OLIGOTHIOPHENES [J].

BAUERLE, P ;

WURTHNER, F ;

GOTZ, G ;

EFFENBERGER, F .

SYNTHESIS-STUTTGART, 1993, (11) :1099-1103

[2] Electroluminescence from new polynorbornenes that contain blue-light-emitting and charge-transport side chains [J].

Boyd, TJ ;

Geerts, Y ;

Lee, JK ;

Fogg, DE ;

Lavoie, GG ;

Schrock, RR ;

Rubner, MF .

MACROMOLECULES, 1997, 30 (12) :3553-3559

[3] PERFLUOROALKYLATIONS AND PERFLUOROOXAALKYLATIONS .3. CHLOROSUBSTITUTED DIAZINES AS SUBSTRATES IN COPPER-MEDIATED CROSS-COUPLING [J].

CHEN, GJ ;

CHEN, LS .

JOURNAL OF FLUORINE CHEMISTRY, 1995, 73 (01) :113-119

[4]

CHENGXUE Z, 1982, J ORG CHEM, V47, P2009

[5] STRUCTURE PROPERTY RELATIONSHIPS FOR THE THERMAL PHASE-BEHAVIOR OF DISCOTIC LIQUID-CRYSTALS - THE EFFECT OF BRANCHING AND UNSATURATION IN THE SIDE-CHAINS OF DISK-LIKE MOLECULES [J].

COLLARD, DM ;

LILLYA, CP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (23) :8577-8583

[6]

Dierking I., 2003, TEXTURES LIQUID CRYS, P91

[7] Building blocks for N-type molecular and polymeric electronics.: Perfluoroalkyl- versus alkyl-functionalized ligothiophenes (nTs; n=2-6).: Systematic synthesis, spectroscopy, electrochemistry, and solid-state organization [J].

Facchetti, A ;

Yoon, MH ;

Stern, CL ;

Hutchison, GR ;

Ratner, MA ;

Marks, TJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (41) :13480-13501

[8]

Facchetti A, 2000, ANGEW CHEM INT EDIT, V39, P4547, DOI 10.1002/1521-3773(20001215)39:24<4547::AID-ANIE4547>3.0.CO

[9]

2-J

[10] High carrier mobility up to 0.1 cm2V-1s-1 at ambient temperatures in thiophene-based smectic liquid crystals [J].

Funahashi, M ;

Hanna, JI .

ADVANCED MATERIALS, 2005, 17 (05) :594-+

← 1 2 3 →