Isolable chiral aggregates of achiral π-conjugated carboxylic acids

Chemistry : a European Journal
Jin-Song ZhaoYun-Bao Jiang

Abstract

The induced aggregation of achiral building blocks by a chiral species to form chiral aggregates with memorized chirality has been observed for a number of systems. However, chiral memory in isolated aggregates of achiral building blocks remains rare. One possible reason for this discrepancy could be that not much is understood in terms of designing these chiral aggregates. Herein, we report a strategy for creating such isolable chiral aggregates from achiral building blocks that retain chiral memory after the facile physical removal of the chiral templates. This strategy was used for the isolation of chiral homoaggregates of neutral achiral π-conjugated carboxylic acids in pure aqueous solution. Under what we have termed an "interaction-substitution" mechanism, we generated chiral homoaggregates of a variety of π-conjugated carboxylic acids by using carboxymethyl cellulose (CMC) as a mediator in acidic aqueous solutions. These aggregates were subsequently isolated from the CMC templates whilst retaining their memorized supramolecular chirality. Circular dichroism (CD) spectra of the aggregates formed in the acidic CMC solution exhibited bisignated exciton-coupled signals of various signs and intensities that were maintained in...Continue Reading

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Citations

Aug 30, 2014·ChemSusChem·Stéven RenaultKristina Edström
Dec 29, 2015·Journal of Polymer Science. Part B, Polymer Physics·Carlos G LopezJoão T Cabral
Sep 26, 2013·Chemical Society Reviews·Yu WangZhong-Qun Tian

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