Photochemical Generation of 9H‐Fluorenyl Radicals
Photochemistry and Photobiology2013Vol. 90(2), pp. 470–475
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Tatiana Dyblenko, Andrei Chtchemelinine, Ryan Reiter, Ruhul Q. Chowdhury, Alexander Enaya, Hanan Afifi, René Fournier, Gabriela Mladenova, Alfred Barry P. Lever, Edward Lee‐Ruff
Abstract
A series of 9-substituted fluorenols and 9,9'-disubstituted-9,9'-bifluorenyls were irradiated to give products derived from fluorenyl radicals. Product distribution was solvent dependent. A TEMPO adduct was isolated from the photoexcitation of 9-fluorenol. An unusual unsymmetrical 3,9'-bifluorenyl was observed from the photolysis of 9-trifluoromethylfluorenol and 9,9'-di(trifluoromethyl)-9,9'-bifluorenyl in more polar or hydrogen-bonding solvents. The electronic nature of 9-substituted fluorenyl radicals was probed using theoretical calculations showing the dipolar character of species with electron-deficient groups. These constitute the first examples of "doubly destabilized" radicals.
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