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Fibrous architectures and organogels of tris(phenylethynylphenyl)adamantane molecules with amino acid moieties: Their solvato‐controlled helicity induction
Author(s) -
Tominaga Masahide,
Azumaya Isao
Publication year - 2011
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.20964
Subject(s) - chemistry , solvophobic , adamantane , molecule , chirality (physics) , alkyl , stacking , crystallography , circular dichroism , hydrogen bond , amide , van der waals force , stereochemistry , polymer chemistry , organic chemistry , quark , chiral symmetry breaking , physics , quantum mechanics , nambu–jona lasinio model
Non‐disk‐shaped molecules self‐assembled to form columnar‐type helical aggregates with gel ability through π‐stacking interactions among the central tris(phenylethynylphenyl)adamantane moieties, hydrogen‐bonding interactions among the alanine parts with amide groups, and van der Waals interactions among the alkyl groups in nonpolar n ‐alkanes. The structural analyses of fibrous architectures with helicity were examined by FTIR, UV‐Vis, and circular dichroism (CD) spectroscopy and FE‐SEM measurements. In contrast, the formation of fibrous structures was observed from adamantane‐based tripodal molecules due to solvophobic interactions in polar EtOH, which showed no detectable Cotton effect in the CD measurement, indicating the induction of solvato‐controlled helicity in the self‐assembly process. Chirality 2011. © 2011 Wiley Periodicals, Inc.