Azumi, Reiko; Mena-Osteritz, Elena; Boese, Roland; Benet-Buchholz, Jordi; Baeuerle, Peter:

The longest oligothiophene ever examined by X-ray structure analysis.

In: Journal of Materials Chemistry, Jg. 16 (2006) ; Nr. 8, S. 728-735
ISSN: 0959-9428
Zeitschriftenaufsatz / Fach: Chemie
The a-conjugated and structurally defined dodecithiophene 1 well crystallizes from soln. into single crystals which were studied by x-ray structure anal. Mol. conformations and packing of the longest oligothiophene ever structurally characterized were detd. Surprisingly, rather rare syn-conformations at the terminal thiophene rings and partial twisting of alkyl side chains for compact packing were found, whereby the mols. form a layer-like arrangement with partial overlap of their heteroarom. systems. In comparison, the mol. properties of the oligomer in a 2D self-assembled monolayer adsorbed at the liq.-solid interface were studied by scanning tunneling microscopy (STM). In comparison to the 3D bulk material, on graphite, a different mol. 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 consts. were detd. which originate from mol.-substrate interactions.

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