Issue 32, 2007

Molecular ordering in bis(phenylenyl)bithiophenes

Abstract

The crystal structure of phenylene–bithiophene oligomers (PTTP) has been investigated by powder X-ray diffraction measurements and ab initio Monte Carlo modelling. Two new hydroxyl-terminated PTTP powders, 5,5′-bis-4-(6-hydroxyhexyloxy)-phenyl-2,2′-bithiophene and the shorter alkyl chain substituted oligomer 5,5′-bis(4-hydroxyphenyl)-2,2′-bithiophene, are compared to single crystals of 5,5′-bis(4-ethylphenyl)-2,2′-bithiophene. The new molecules are characterized by a close packed, distorted hexagonal array with tilted short axes in a herringbone-type structure. Neighbouring molecules within layers are displaced along the long axis. Modelling the electrostatic potential surface suggests that electrostatic interactions are responsible for the observed herringbone-like ordering. Alkyl chains facilitate a partial mixing through interdigitation of aromatic and aliphatic moieties.

Graphical abstract: Molecular ordering in bis(phenylenyl)bithiophenes

Supplementary files

Additions and corrections

Article information

Article type
Paper
Submitted
23 Jan 2007
Accepted
24 May 2007
First published
05 Jun 2007

J. Mater. Chem., 2007,17, 3427-3432

Molecular ordering in bis(phenylenyl)bithiophenes

M. A. Stokes, R. Kortan, S. R. Amy, H. E. Katz, Y. J. Chabal, C. Kloc and T. Siegrist, J. Mater. Chem., 2007, 17, 3427 DOI: 10.1039/B701035D

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