Counteranion driven homochiral assembly of a cationic C-3-symmetric gelator through ion-pair assisted hydrogen bond

TitleCounteranion driven homochiral assembly of a cationic C-3-symmetric gelator through ion-pair assisted hydrogen bond
Publication TypeJournal Article
Year of Publication2016
AuthorsMaity, A, Gangopadhyay, M, Basu, A, Aute, S, Babu, SSanthosh, Das, A
JournalJournal of the American Chemical Society
Volume138
Issue35
Pagination11113-11116
Date PublishedSEP
Type of ArticleArticle
ISSN0002-7863
Abstract

The helical handedness in achiral self-assemblies is mostly complex due to spontaneous symmetry breaking or kinetically controlled random assembly formation. Here an attempt has been made to address this issue through chiral anion exchange. A new class of cationic achiral C-3-symmetric gelator devoid of any conventional gelation assisting functional units is found to form both right-and left-handed helical structures. A chiral counteranion exchange-assisted approach is successfully introduced to control the chirality sign and thereby to obtain preferred homochiral assemblies. Formation of anion-assisted chiral assembly was confirmed by circular dichroism (CD) spectroscopy, microscopic images, and crystal structure. The X-ray crystal structure reveals the construction of helical assemblies with opposite handedness for (+)- and (-)-chiral anion reformed gelators. The appropriate counteranion driven ion-pair-assisted hydrogen-bonding interactions are found responsible for the helical bias control in this C-3-symmetric gelator.

DOI10.1021/jacs.6b06312
Type of Journal (Indian or Foreign)Foreign
Impact Factor (IF)13.038
Divison category: 
Organic Chemistry
Physical and Materials Chemistry

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