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  • A 2-hydroxyphenacyl moiety absorbing below 370 nm is proposed as a new photoremovable protecting group for carboxylates and sulfonates. Laser flash photolysis and steady-state sensitization studies show that the leaving group is released from a short-lived triplet state. In addition, DFT-based quantum chemical calculations were performed to determine the key reaction steps. We found that triplet excited state intramolecular proton transfer represents a major deactivation channel. Minor productive pathways involving the triplet anion and quinoid triplet enol intermediates have also been identified.
  • A 2-hydroxyphenacyl moiety absorbing below 370 nm is proposed as a new photoremovable protecting group for carboxylates and sulfonates. Laser flash photolysis and steady-state sensitization studies show that the leaving group is released from a short-lived triplet state. In addition, DFT-based quantum chemical calculations were performed to determine the key reaction steps. We found that triplet excited state intramolecular proton transfer represents a major deactivation channel. Minor productive pathways involving the triplet anion and quinoid triplet enol intermediates have also been identified. (en)
Title
  • 2-Hydroxyphenacyl ester: a new photoremovable protecting group
  • 2-Hydroxyphenacyl ester: a new photoremovable protecting group (en)
skos:prefLabel
  • 2-Hydroxyphenacyl ester: a new photoremovable protecting group
  • 2-Hydroxyphenacyl ester: a new photoremovable protecting group (en)
skos:notation
  • RIV/00216224:14310/12:00058037!RIV13-GA0-14310___
http://linked.open...avai/riv/aktivita
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  • P(ED0001/01/01), P(GA203/09/0748), P(ME09021), S
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  • 9
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  • 183331
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  • RIV/00216224:14310/12:00058037
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  • Photochemistry; 2-Hydroxyphenacyl ester; photoremovable protecting group (en)
http://linked.open.../riv/klicoveSlovo
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  • GB - Spojené království Velké Británie a Severního Irska
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  • [D0AF0C2B7216]
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  • Photochemical & Photobiological Sciences
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  • 11
http://linked.open...iv/tvurceVysledku
  • Klán, Petr
  • Heger, Dominik
  • Šolomek, Tomáš
  • Givens, Richard
  • Ngoy, Bokolombe Pitchou
  • Park, Bong Ser
  • Šebej, Peter
  • Lim, Bum Hee
  • Pastierik, Tomáš
http://linked.open...ain/vavai/riv/wos
  • 000307583800008
issn
  • 1474-905X
number of pages
http://bibframe.org/vocab/doi
  • 10.1039/C2PP25133G
http://localhost/t...ganizacniJednotka
  • 14310
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