Photophysical properties of pyrene-containing biphotocromic dyads and corresponding cyclobutanes formed from dyads in the [2+2] photocycloaddition reaction

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Abstract

The photophysical properties of biphotochromic dyads DoX and D10 containing two identical photochromes, 2-[2-(pyrene-1-yl)ethenyl]-quinoline (PEQ), linked by bridge groups of different lengths, as well as the corresponding dipyrenylcyclobutanes CBoX and CB10 formed from the dyads in the [2+2] photocycloaddition reaction (PCA) have been investigated by time-resolved emission spectroscopy (TRES). On the basis of TRES, the number of emitters was determined, their emission spectra, excited state lifetimes, and rate constants of competitive physical and chemical processes (emission, energy transfer, and reactions) were calculated. In dyads, the formation of excimers, possible intermediates of the PCA reaction, was detected by the appearance of emitters with lifetimes significantly increased compared to the model PEQ-photochrome. In cyclobutanes, a decrease in the lifetime of pyrene substituents as compared to 1-methylpyrene shows the energy transfer from substituents to the cyclobutane ring, which, according to the predissociation mechanism, initiates the ring-opening reaction (retro-PCA). In addition, CBoX shows the presence of non-emitting conformers. Quantum chemical calculations by DFT method confirmed the possibility of formation of different conformers of cyclobutane CBoX, differing in the relative position of pyrenyl substituents and the degree of their interaction with each other.

About the authors

M. F. Budyka

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

Email: budyka@icp.ac.ru
Chernogolovka, Russia

V. M. Li

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

Email: budyka@icp.ac.ru
Chernogolovka, Russia

T. N. Gavrishova

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

Email: budyka@icp.ac.ru
Chernogolovka, Russia

S. A. Tovstun

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

Chernogolovka, Russia

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