Supramolecular polymerization and gel formation of bis(merocyanine) dyes driven by dipolar aggregation

Journal of the American Chemical Society
S YaoFrank Würthner

Abstract

Two highly dipolar merocyanine dyes were tethered by a rigid tris(n-dodecyloxy)xylylene unit that preorganizes the dyes for a supramolecular polymerization process through intermolecular aggregation of the dyes. UV/vis spectroscopy revealed a solvent dependent equilibrium between monomeric dyes and two different types of dye aggregates that are characterized by hypsochromically shifted D- and H-type absorption bands. Taking into account the ditopic nature of the supramolecular building blocks, the occurrence of the D-band indicates the formation of an oligomeric/polymeric supramolecular chain whereas the observation of the H-band suggests a higher order assembly. For the H-aggregated dyes, intrinsic viscosities exceed 0.65 L g(-1) in methylcyclohexane, values typically found for macromolecular solutions. At higher concentration, further association of these aggregates takes place by entanglement of the alkyl groups leading to a substantial increase in viscosity and gelation. Rheology studies show linear viscoelastic behavior which was attributed to the formation of an entangled dynamic network. AFM and cryo-TEM studies of the gel reveal long and stiff rod-type assemblies. X-ray diffraction studies for a solid film show columnar...Continue Reading

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Citations

Feb 9, 2006·Chemical Communications : Chem Comm·Zhimou YangBing Xu
Mar 27, 2009·Chemical Society Reviews·Francisco VeraTeresa Sierra
Feb 18, 2010·Chemical Communications : Chem Comm·Ho-Joong KimMyongsoo Lee
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Jul 9, 2009·Angewandte Chemie·Andreas LohrFrank Würthner
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