Photochemical Generation of 9H‐Fluorenyl Radicals |
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| Authors: | Tatiana Dyblenko Andrei Chtchemelinine Ryan Reiter Ruhul Q Chowdhury Alexander Enaya Hanan Afifi Rene Fournier Gabriela Mladenova Alfred Barry P Lever Edward Lee‐Ruff |
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| Institution: | 1. Department of Chemistry, York University, , Toronto, ON, Canada;2. Beni‐Suef University, , Egypt |
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| 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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