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Helicity of perfluoroalkyl chains controlled by the self‐assembly of the Ala‐Ala dipeptides
Author(s) -
Zhang Lianglin,
Lin Shuwei,
Tong Qiyun,
Li Yan,
Wang Yong,
Li Yi,
Li Baozong,
Yang Yonggang
Publication year - 2019
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.23130
Subject(s) - chemistry , helicity , chirality (physics) , stereochemistry , combinatorial chemistry , nanotechnology , computational chemistry , physics , quantum mechanics , nambu–jona lasinio model , quark , chiral symmetry breaking , materials science , particle physics
Four Ala‐Ala dipeptides with a perfluoroalkyl chain at the N‐terminal were synthesized. They were able to self‐assemble into helical nanofibers and/or twisted nanobelts in a mixture of DMSO/H 2 O. The handedness of nanofibers and nanobelts was controlled by the chirality of the alanine at the N‐terminal. The stacking handedness of the phenylene groups and the helicity of the perfluoroalkyl chain were studied using circular dichroism spectroscopy and vibrational circular dichroism, respectively. The chirality of the alanine at N‐terminal controlled the stacking handedness of the neighboring phenylene groups. Moreover, due to the low potential barrier between M‐ and P‐helices of the perfluorocarbon chain, the handedness of the organic self‐assemblies eventually controlled the helicity of the perfluorocarbon chain. X‐ray diffraction indicated that a lamellar structure was formed by the dimers of the dipeptides.