Spectral and photochemical properties of dipyrenylcyclobutanes formed in the [2+2]-photocycloaddition reaction from biphotochromic dyads

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Abstract

The properties of dipyrenylcyclobutanes CB10 and CBoX, which are products of the [2+2]-photocycloaddition reaction (PCA) of the corresponding biphotochromic dyads D10 and DoX, have been studied. The absorption and fluorescence spectra of cyclobutane CBoX revealed the presence of different types of pyrene substituents, with strong and weak interactions in the ground S0 and excited S1 states. In both cyclobutanes, energy transfer (ET) from the pyrenyl substituents to the cyclobutane rings is observed, initiating the cyclobutane opening reaction (retro-PCA), which occurs via a predissociation mechanism. The photochromic pair “D10-CB10” is an example of a new type of photochrome operating by the mechanism of the PCA reaction and can function as a two-channel color-correlated fluorescent photoswitch.

About the authors

M. F. Budyka

Federal Research Center of Problems of Chemical Physics and Medicinal Chemistry of the RAS

Author for correspondence.
Email: budyka@icp.ac.ru
Russian Federation, Chernogolovka

V. M. Li

Federal Research Center of Problems of Chemical Physics and Medicinal Chemistry of the RAS

Email: budyka@icp.ac.ru
Russian Federation, Chernogolovka

T. N. Gavrishova

Federal Research Center of Problems of Chemical Physics and Medicinal Chemistry of the RAS

Email: budyka@icp.ac.ru
Russian Federation, Chernogolovka

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