Towards organic photohydrides: Excited-state behavior of 10-methyl-9-phenyl-9,10-dihydroacridine

X. Yang, J. Walpita, D. Zhou, H.L. Luk, S. Vyas, R.S. Khnayzer, S.C. Tiwari, K. Diri, C.M. Hadad, F.N. Castellano, A.I. Krylov, and K.D. Glusac
J. Phys. Chem. B 117, 15290 – 15296 (2013)

The excited-state hydride release from 10-methyl-9-phenyl-9,10-dihydroacridine (PhAcrH) was investigated using steady-state and time-resolved UV/vis absorption spectroscopy. Upon excitation, PhAcrH is oxidized to the corresponding iminium ion (PhAcr⁺), while the solvent (acetonitrile/water mixture) is reduced (52% of PhAcr⁺ and 2.5% of hydrogen is formed). The hydride release occurs from the triplet excited state by a stepwise electron/hydrogen-atom transfer mechanism. To facilitate the search for improved organic photohydrides that exhibit a concerted mechanism, a computational methodology is presented that evaluates the thermodynamic parameters for the hydride ion, hydrogen atom, and electron release from organic hydrides.

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