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Crystallographic and Spectroscopic Studies of a Host–Guest Complex Consisting of a Novel Zinc Trisporphyrinate and a Chiral Monoamine

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posted on 29.03.2016, 14:24 by Zhen Han, Li Li, Bo Shi, Xianshi Fang, Yong Wang, Chuanjiang Hu
We have designed and synthesized a novel zinc trisporphyrinate with a benzene tricarboxamide as the linker. In the presence of a large excess of 1-phenylethylamine, single crystals of the corresponding 1:3 host–guest complex were obtained, which provide the crystallographic structure of a host–guest complex consisting of an achiral porphyrin and a chiral monoamine. The structure reveals the 1-phenylethylamines adopt the “inside” binding mode that is stabilized by intramolecular hydrogen bonds. The NH2 of the 1-phenylethylamine is involved in both coordination and hydrogen bonding interactions. Circular dichroism (CD) and ultraviolet–visible spectra revealed that the 1:3 host–guest complex is dominant in the presence of a large excess of 1-phenylethylamine. The crystal structure shows there are two diastereomers of the 1:3 host–guest complexes. Density functional theory and TDDFT calculations suggest that one of the diastereomers is more energetically favorable, which dominates the CD signals.