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Self‐Assembled Boronic Ester Cavitand Capsules with Various Bis(catechol) Linkers: Cavity‐Expanded and Chiral Capsules
Author(s) -
Tamaki Kento,
Ishigami Asumi,
Tanaka Yasutaka,
Yamanaka Masamichi,
Kobayashi Kenji
Publication year - 2015
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.201501717
Subject(s) - cavitand , catechol , chemistry , boronic acid , combinatorial chemistry , self assembly , resorcinarene , polymer chemistry , organic chemistry , supramolecular chemistry , molecule
Two molecules of cavitand tetraboronic acid and four molecules of various bis(catechol) linkers self‐assemble into capsules through the formation of eight dynamic boronic ester bonds. Each capsule has a different cavity size depending on the linker used, and shows particular guest encapsulation selectivity. A chiral capsule made up of the cavitand and a chiral bis(catechol) linker was also constructed. This capsule induces supramolecular chirality with respect to a prochiral biphenyl guest by diastereomeric encapsulation through the asymmetric suppression of rotation around the axis of the prochiral biphenyl moiety.