Relationship between Separation Behavior and Structural Flexibility in Inclusion Crystal of Cholic Acid

Selective incorporation of two aromatic compounds, benzene and ethylbenzene,into an inclusion crystal of cholic acid was investigated. Addition of an excessamount of 1:1 mixture of benzene and ethylbenzene into saturated solution ofcholic acid in 1-butanol led to a spontaneous formation of an inclusion crystal.The co-crystal contained benzene and ethylbenzene at the constant molar ratioof 8:2 irrespective of the relative concentrations of guest and host in the feedsolution, indicating that the resulting crystal consists of the two guests mixedin a single host framework. The resulting ternary crystal had thermal behaviorsimilar to a binary crystal obtained from benzene. In contrast to the guest/hostratio, the benzene/ethylbenzene ratio in the feed solution affected that in theinclusion crystal. Benzene was basically preferred in the cholic acid crystalover ethylbenzene, but the selectivity reversed at an excess amount of ethylbenzene.This separation behavior can be understood in terms of the structural flexibility ofhost frameworks.