Optically probing molecular shuttling motion of [2]rotaxane by a conformation-adaptive fluorophore

A bistable [2]rotaxane with a conformation-adaptive macrocycle bearing a 9,14-diphenyl-9,14-dihydrodibenzo[a,c]phenazine (DPAC) unit was synthesized, which could be utilized to optical probe the molecular shuttling motion of the functionalized rotaxane system. The UV-vis, H-1 NMR and PL spectroscopic data clearly demonstrated that the DPAC ring was interlocked onto the thread and the fluorescence intensity of the DPAC unit in the macrocycle was effectively regulated by the location change of the macrocycle along the thread under acid/base stimulation, which was attributed to the modulation of the intramolecular photo-induced electron transfer between the DPAC unit and the methyltriazole (MTA) unit. This bistable rotaxane system containing a conformation-adaptive fluorophore unit in the macrocycle moiety opens an alternative way to design functional bistable mechanically interlocked molecules. (C) 2022 Published by Elsevier B.V. on behalf of Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences.

Automated summary

A bistable [2]rotaxane with a conformation-adaptive macrocycle was synthesized and utilized to probe the molecular shuttling motion. The fluorescence intensity was controlled by the modulation of intramolecular photo-induced electron transfer.