Title
Reinvestigation of the photoreaction of 1,4-bis(2,4,6-triphenylpyridinio)benzene: Synthesis of a diazonia derivative of hexabenzoperylene by multiple photocyclization
Author
Kiyoshi Sato, Yuta Seki, Shotaro Suga, Yusuke Ikeda, Motowo Yamaguchi
Year
2016
Journal
Journal of Photochemistry and Photobiology A: Chemistry
Abstract
The photo-induced oxidative cyclization of the 1,1′-p-phenylene-bis(2,4,6-triphenylpyridinium) was reinvestigated. While mono-cyclization was claimed to be the photoproduct in a previous report, it was found that the diazonia derivative of hexabenzoperylene can be formed as the final photoproduct by four-fold cyclization. The photoreaction affords one of the two possible stereoisomers (twisted and anti forms), and the stereostructure of the product is assigned to the twisted form by 1H NMR titration study with a chiral complexing reagent and by analysis of the absorption spectrum using TD-DFT calculations. The diazonia derivative of hexabenzoperylene exhibits yellow and red luminescence in the solution and solid states respectively and possesses well-separated four-reversible one-electron reduction potentials.
Instrument
FP-8300
Keywords
Fluorescence, Quantum yield, Solid-state, Chemical stability, Organic chemistry