Time-resolved resonance Raman study of the triplet states of p-hydroxyacetophenone and the p-hydroxyphenacyl diethyl phosphate phototrigger compound

The Journal of Organic Chemistry
Chensheng MaDavid Lee Phillips

Abstract

Pico- and nanosecond time-resolved resonance Raman (TR3) spectroscopy have been utilized to study the dynamics and structure of p-hydroxyacetophenone (HA) and the p-hydroxyphenacyl-caged phototrigger compound p-hydroxyphenacyl diethyl phosphate (HPDP) in acetonitrile solution. Transient intermediates were detected and attributed to the triplet states of HA and HPDP. Nanosecond-TR3 measurements were done for two isotopically substituted HA molecules to help better assign the triplet state carbonyl C=O stretching and the ring related vibrational modes. The dynamics of formation and the spectral characteristics for the triplet states were found to be similar for the HA and HPDP. The temporal evolution at very early picosecond time scale indicates there is rapid intersystem crossing (ISC) conversion and subsequent relaxation of the excess energy of the initially produced energetic triplet state. B3LYP/6-311G** density functional theory (DFT) calculations were done to determine the structures and vibrational frequencies for both the triplet and ground states of HA and HPDP. The calculated spectra reproduce the experimental spectra and the observed isotopic shifts reasonably well and were used to make tentative assignments to all the...Continue Reading

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Citations

Mar 11, 2016·The Journal of Physical Chemistry. B·Amanda L HoukChristopher G Elles
Sep 17, 2015·The Journal of Organic Chemistry·Iwona BownikPetr Klán
Feb 22, 2012·Photochemical & Photobiological Sciences : Official Journal of the European Photochemistry Association and the European Society for Photobiology·Richard S GivensJakob Wirz
Dec 7, 2013·Photochemical & Photobiological Sciences : Official Journal of the European Photochemistry Association and the European Society for Photobiology·Sanjeewa N SenadheeraRichard S Givens
Sep 24, 2014·Beilstein Journal of Organic Chemistry·Sanjeewa N SenadheeraRichard S Givens
Mar 25, 2005·The Journal of Organic Chemistry·Armands KonosonoksAnna D Gudmundsdóttir
Mar 10, 2011·The Journal of Organic Chemistry·Marek RemešRichard S Givens

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