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Hexabenzocoronene Graphitic Nanocoils Appended with Crown Ethers: Supramolecular Chirality Induced by Host–Guest Interaction
Author(s) -
Zeng Wang,
Zhang Wei,
Li Xianying,
Jin Wusong,
Zhang Dengqing
Publication year - 2019
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201904291
Subject(s) - triethylene glycol , circular dichroism , crown ether , supramolecular chirality , supramolecular chemistry , chirality (physics) , amino acid , enantiomer , stereochemistry , dendrimer , chemistry , polymer chemistry , optically active , ether , materials science , crystallography , organic chemistry , crystal structure , chiral symmetry breaking , biochemistry , ion , nambu–jona lasinio model , physics , quantum mechanics , quark
We have designed and synthesized two new achiral hexa‐ peri ‐hexabenzocoronene (HBC) derivatives, HBC CE and HBC TEG‐CE , which bear the crown ether as the pendant for the amino acid binding site. The HBC CE self‐assembled into a racemic mixture of P ‐ and M ‐handed helical nanocoils, however, in the presence of chiral amino acid guests, it formed helical nanocoils with one‐handed screw sense. The effects of the concentration, type and configuration of the guests on the induced circular dichroism (ICD) during the co‐assembly of HBC CE with chiral amino acids were also investigated. Additionally, after complete removal of the chiral guests, the optically active nanocoils did not racemize, even in the presence of excess amino acids with the opposite configuration. In contrast, HBC TEG‐CE with a long triethylene glycol (TEG) chain between the crown ether group and the HBC unit did not exhibit ICD during the co‐assembly with chiral amino acids.