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Chirality Organization in Phenylenediamines Induced by a Nonpeptidic Reverse‐Turn
Author(s) -
Moriuchi Toshiyuki,
Ohmura Satoshi D.,
Morita Kenji,
Hirao Toshikazu
Publication year - 2012
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201200022
Subject(s) - chemistry , intramolecular force , chirality (physics) , hydrogen bond , conjugated system , turn (biochemistry) , redox , stereochemistry , axial chirality , photochemistry , catalysis , molecule , organic chemistry , enantioselective synthesis , polymer , biochemistry , chiral symmetry breaking , physics , quantum mechanics , nambu–jona lasinio model , quark
The introduction of amino acid moieties into phenylenediamine derivatives is demonstrated to induce chirality in the π‐conjugated backbones and results in the formation of a nonpeptidic reverse‐turn conformation through intramolecular hydrogen bonds. The formation of the intramolecular hydrogen bonds plays an important role in the stabilization of the phenylenediamine radical cation, as the chirality‐organized structure is preserved through the intramolecular hydrogen bonding. The designed phenylenediamines have luminescent switching properties based on the redox states of the phenylenediamine moieties.