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Structural Transformation of the 2‐( p ‐Aminophenyl)‐1‐hydroxyinden‐3‐ylmethyl Chromophore as a Photoremovable Protecting Group
Author(s) -
Sasaki Miyu,
Tran Bao Nguyen Linh,
Yabumoto Sohshi,
Nakagawa Tatsuo,
Abe Manabu
Publication year - 2020
Publication title -
chemphotochem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.13
H-Index - 18
ISSN - 2367-0932
DOI - 10.1002/cptc.202000149
Subject(s) - chromophore , benzoic acid , quantum yield , chemistry , yield (engineering) , dimethyl sulfoxide , photochemistry , methanol , photodissociation , reactivity (psychology) , carbocation , molecule , functional group , organic chemistry , fluorescence , materials science , polymer , medicine , physics , alternative medicine , pathology , quantum mechanics , metallurgy
Photoremovable protecting groups (PPGs) have attracted much attention not only in the field of organic synthesis but also in biology and materials science because of the spatiotemporally controlled release of various functional molecules upon photolysis. In this study, a new PPG, the 2‐( p ‐aminophenyl)‐1‐hydroxyinden‐3‐ylmethyl (pAPHi) chromophore, is designed and synthesized for the efficient and fast release of functional molecules with high conversion yields. The photolysis of caged benzoic acid with the pAPHi chromophore in dimethyl sulfoxide released benzoic acid in 96 % yield, with a decomposition quantum yield of 13 %. A high quantum yield of 51 % was observed with the clean formation of benzoic acid (94 % yield) in methanol. Transient absorption spectroscopic analyses clarified the generation of an intermediate carbocation as well as its reactivity.