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Chiral Symmetry Breaking of Spiropyrans and Spirooxazines by Dynamic Enantioselective Crystallization
Author(s) -
Ishikawa Hiroki,
Uemura Naohiro,
Saito Rei,
Yoshida Yasushi,
Mino Takashi,
Kasashima Yoshio,
Sakamoto Masami
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.201901889
Subject(s) - crystallization , enantioselective synthesis , circular dichroism , crystallography , materials science , chiral symmetry breaking , symmetry breaking , optical rotation , crystal (programming language) , photochemistry , chemistry , organic chemistry , catalysis , physics , quantum mechanics , computer science , programming language
Dynamic enantioselective crystallization enabled the chiral symmetry breaking of two spiropyrans and one spirooxazine. The three spiro compounds afforded racemic conglomerate crystals, and easily racemized in alcoholic solution without irradiation. Optically pure enantiomorphic crystals were obtained by vapor‐diffusion crystallization or attrition‐enhanced deracemization (Viedma ripening). Their absolute configurations were determined by single‐crystal X‐ray analysis and each enantiomorphic crystal was correlated with its solid‐state circular dichroism (CD) spectrum.