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Design, Synthesis, and Photochemical Properties of Clickable Caged Compounds
Published on: October 15, 2019
Cucurbit[7]uril-Encapsulation-Controlled Supramolecular Photoproduct and Radical Fluorescence Emission
Min Peng1, Yi Luo1, Yutao Rao1
1Key Laboratory of Chemical Biology and Traditional Chinese Medicine, Key Laboratory of the Assembly and Application of Organic Functional Molecules of Hunan Province, Hunan Normal University, Changsha, Hunan, 410081, P. R. China.
Abstract:
Herein, a host-guest interaction-controlled photoproduct created by using cucurbit[7]uril (Q[7])-based pseudorotaxane structures is reported. The assembly exhibited controlled behavior towards the reduction of the ethylene (C=C) bond in the tetrakis(pyridin-4-yl)ethylene (TPyE) guest molecule under UV light irradiation. This can be attributed to the Q[7] encapsulation masking the four pyridinium arms of the guest, which inhibits planarization of the TPyE core to form the cyclization product. In particular, the strong affinity of Q[7] for the butyl-substituted guest (TPyE-4C) led to an unusual radical fluorescence emission of the photoirradiation-triggered intermediate of the guest molecule being observed in aqueous solution. This work provides a valuable paradigm and new insight for macrocycle-based host-guest interactions in supramolecular catalysis and luminescent radical materials.
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