Competitive inclusion of disubstituted benzene regioisomers with crystals of p-tert-butylcalix[4]arene

Naoya Morohashi, Ayano Tonosaki, Taro Kitagawa, Takuro Sasaki, Kohei Ebata, Tetsutaro Hattori

Research output: Contribution to journalArticlepeer-review

18 Citations (Scopus)


A crystal of p-tert-butylcalix[4]arene (1) has selectively included regioisomers of eight different disubstituted benzenes, giving inclusion crystals classified into four types: 2:1 (host/guest) with p-isomer and 1:1 with o-, m-, and p-isomers. X-ray crystallographic analysis of 12p-xylene, 1ocresol, 1m-dichlorobenzene, and 1p-chlorotoluene, which were chosen as representatives for the individual types of inclusion crystals, revealed that the electrostatic properties and steric bulk of the substituents in the rigid guest molecules are efficiently reflected in the interaction with the host molecules, which construct flexible bilayer-based packing structures in the inclusion crystals. This is considered as a principal origin for the high selectivity and wide applicability achieved in the inclusion of aromatic regioisomers with crystals of compound 1.

Original languageEnglish
Pages (from-to)5038-5043
Number of pages6
JournalCrystal Growth and Design
Issue number10
Publication statusPublished - 2017 Oct 4


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