Jump to main content
Jump to site search

Issue 12, 1998
Previous Article Next Article

Photoinduced electron transfer from isoprenoid polyalkene acetates to dicyanoarenes


Photoinduced electron transfer from electron donors, such as prenyl acetate (D-0), geranyl acetate (D-1), all-trans-farnesyl acetate (D-2) or all-trans-geranylgeranyl acetate (D-3) to 1,4-dicyano-2,3,5,6-tetramethylbenzene (A-1), 1,4-dicyanonaphthalene (A-3) and 9,10-dicyanoanthracene (A-5) in the presence of 1,1'-biphenyl (BP) as co-donor was studied in acetonitrile by time-resolved UV–VIS spectroscopy and conductivity. The main transients observed for A-1, A-3 (λexc = 308 nm) and A-5 (λexc = 353 nm) in deoxygenated acetonitrile are the radical cation of BP (BP˙+) and the radical anion of the respective electron acceptors. Oxidation potentials of 2.1, 1.8 and 1.7 V for D-0, D-1 and D-2, respectively, are consistent with data obtained from steady-state fluorescence quenching of the electron acceptors and decay of BP·+ both occurring via electron transfer. A conductivity component in the millisecond time range upon excitation of A-1 or A-3 in the presence of BP and D-n in aqueous acetonitrile is ascribed to a proton which is released upon nucleophilic addition of water to the radical cation of the donor (D-n˙+) and subsequently reacts with an intermediate in the cyclization pathway. The mechanism of the photocyclization of D-1, involving initially a reaction of D-1˙+ with water, is discussed in detail.

Back to tab navigation

Article type: Paper
DOI: 10.1039/A800322J
J. Chem. Soc., Faraday Trans., 1998,94, 1701-1706

  •   Request permissions

    Photoinduced electron transfer from isoprenoid polyalkene acetates to dicyanoarenes

    K. Warzecha, H. Görner and M. Demuth, J. Chem. Soc., Faraday Trans., 1998, 94, 1701
    DOI: 10.1039/A800322J

Search articles by author