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Chiral amphiphilic self-assembled α,α'-linked quinque-, sexi-, and septithiophenes: synthesis, stability and odd-even effects

Henze, O.; Feast, W.J.; Gardebien, F.; Jonkheijm, P.; Lazzaroni, R.; Meijer, E.W.; Leclere, p.; Schenning, A.P.H.J.

Authors

O. Henze

W.J. Feast

F. Gardebien

P. Jonkheijm

R. Lazzaroni

E.W. Meijer

p. Leclere

A.P.H.J. Schenning



Abstract

The synthesis, characterization, and self-assembly in butanol of a series of well-defined ,'-linked quinqui-, sexi-, and septithiophenes substituted, via ester links at their termini, by chiral oligo(ethylene oxide) chains carrying an , , , and methyl, respectively, are reported. Studies of the self-assembly of these molecules using UV/visible absorption, luminescence, and circular dichroism spectroscopies reveal, for the sexithiophene case, that the magnitude of the observed Cotton effect in the aggregates diminishes progressively as the chiral substituent is moved away from the thiophene segment. The stability of the assemblies increases with the length of the oligothiophene and as the substituent chiral unit is moved away from the aromatic core, being greatest for the unsubstituted case. The sign of the Cotton effect alternates in an "odd/even" manner as the position of the chiral substituent is moved along the oligo(ethylene oxide) chain and on going from the quinquethiophene to the septithiophene having the same side chain. Atomic force microscopy on materials deposited from solution on an aluminum or glass surface and optical measurements show that capsules are formed from the oligothiophenes with H-type packing of the aromatic segments.

Citation

Henze, O., Feast, W., Gardebien, F., Jonkheijm, P., Lazzaroni, R., Meijer, E., …Schenning, A. (2006). Chiral amphiphilic self-assembled α,α'-linked quinque-, sexi-, and septithiophenes: synthesis, stability and odd-even effects. Journal of the American Chemical Society, 128(17), 5923-5929. https://doi.org/10.1021/ja0607234

Journal Article Type Article
Publication Date 2006-05
Deposit Date Apr 25, 2007
Journal Journal of the American Chemical Society
Print ISSN 0002-7863
Electronic ISSN 1520-5126
Publisher American Chemical Society
Peer Reviewed Peer Reviewed
Volume 128
Issue 17
Pages 5923-5929
DOI https://doi.org/10.1021/ja0607234