Issue 8, 2006

The longest oligothiophene ever examined by X-ray structure analysis

Abstract

The α-conjugated and structurally defined dodecithiophene 1 well crystallizes from solution into single crystals which were investigated by X-ray structure analysis. Molecular conformations and packing of the longest oligothiophene ever structurally characterized were determined. Surprisingly, rather rare syn-conformations at the terminal thiophene rings and partial twisting of alkyl side chains for compact packing were found, whereby the molecules form a layer-like arrangement with partial overlap of their heteroaromatic systems. In comparison, the molecular properties of the oligomer in a 2D self-assembled monolayer adsorbed at the liquid–solid interface were investigated by scanning tunnelling microscopy (STM). In comparison to the 3D bulk material, on graphite, a different molecular arrangement was found. A lamella-type ordering of molecularly resolved oligomers which exhibit an all-anti conformation could be imaged over wide areas. Larger lattice constants were determined which originate from molecule–substrate interactions.

Graphical abstract: The longest oligothiophene ever examined by X-ray structure analysis

Supplementary files

Article information

Article type
Paper
Submitted
21 Sep 2005
Accepted
07 Nov 2005
First published
28 Nov 2005

J. Mater. Chem., 2006,16, 728-735

The longest oligothiophene ever examined by X-ray structure analysis

R. Azumi, E. Mena-Osteritz, R. Boese, J. Benet-Buchholz and P. Bäuerle, J. Mater. Chem., 2006, 16, 728 DOI: 10.1039/B513427G

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