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Photophysical properties of 1,3,6,8-tetraarylpyrenes and their cation radicals

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Abstract The synthesis of 1,3,6,8-tetraaryl substituted pyrenes is described. The substituents on the aryl groups influence the optoelectronic properties of the pyrene core indicating a strong coupling between the aryl… Click to show full abstract

Abstract The synthesis of 1,3,6,8-tetraaryl substituted pyrenes is described. The substituents on the aryl groups influence the optoelectronic properties of the pyrene core indicating a strong coupling between the aryl groups and the pyrene core. Electronic absroption spectra of the cation radicals generated in solution by the single electron oxidation of pyrenes reaffirmed the coupling of the aryl rings with the pyrene. The aryl groups at 1,3,6,8-positions completely inhibit the π-stacking of pyrene core in solution. Crystal structure of the cation radical salt of tetraphenyl shows charge delocalization between neutral pyrene unit and two cationic pyrene cores. Complete inhibition of the pyrene core stacking is observed in the solid state of cation radical when the dendritic pentaphenyl groups surround the pyrene core.

Keywords: cation; aryl groups; pyrene core; cation radicals

Journal Title: Journal of Photochemistry and Photobiology A: Chemistry
Year Published: 2019

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