Visible-light-driven two-way photoisomerization of 1-(1-pyrenyl)-2-(2-quinolyl)ethylene in neutral and protonated forms

Abstract

Diarylethylenes with large π-systems often lose their photochemical activity (the size effect). 1-(1-Pyrenyl)-2-(2-quinolyl)ethylene (1P2QE), despite having a large conjugated π-system of 28 electrons, undergoes two-way reversible trans–cis photoisomerization both in the neutral and protonated forms with quantum yields as high as 0.13–0.83. For the neutral 1P2QE, experimental data and quantum-chemical calculations indicate a diabatic (nonadiabatic) reaction mechanism. Due to high photoisomerization quantum yields and the long-wavelength absorption band at 340–460 nm and 390–560 nm for the neutral and protonated compounds, respectively, 1P2QE can be used as a molecular photoswitch that is sensitive to visible light.