NDLI: A spectroscopic study of the excited state proton transfer processes of (8-bromo-7-hydroxyquinolin-2-yl)methyl-protected phenol in aqueous solutions

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A spectroscopic study of the excited state proton transfer processes of (8-bromo-7-hydroxyquinolin-2-yl)methyl-protected phenol in aqueous solutions

Content Provider	Royal Society of Chemistry (RSC)
Author	Deodato, Davide Chiu, Hoi Kei Dore, Timothy M. Huang, Jinqing Lan, Xin Muliawan, Adna P. Phillips, David Lee Li, Ming De Ma, Jiani
Copyright Year	2017
Abstract	A combination of spectroscopic methods and density functional theory (DFT) computations was used to study the excited state proton transfer (ESPT) processes of (8-bromo-7-hydroxyquinolin-2-yl)methyl-protected phenol (BHQ-OPh). Characterization of the prototropic forms of BHQ-OPh in different solvent environments revealed that the neutral form predominates in acetonitrile and in 1 : 1 acetonitrile/water (pH 5.0), whereas the anionic form predominates in 1 : 1 acetonitrile/PBS (pH 7.4). Both the neutral and anionic forms were significantly populated in 1 : 1 acetonitrile/water. Upon irradiation in acetonitrile the triplet neutral form was observed, whereas the triplet anionic form was detected in 1 : 1 acetonitrile/PBS (pH 7.4). The existence of the triplet tautomeric form of BHQ-OPh in both 1 : 1 acetonitrile/water and 1 : 1 acetonitrile/water (pH 5.0), and the ESPT processes from the neutral to the anionic to the tautomeric forms in the excited state were observed using time-resolved spectroscopy. A reaction mechanism in 1 : 1 acetonitrile/water and 1 : 1 acetonitrile/water (pH 5.0) was proposed based on the spectroscopic and DFT computational results. A comparison of the results for BHQ-OPh with those of BHQ-OAc reveals that the initial prototropic states and photochemical processes are similar. The understanding gained of the initial photo-induced processes of BHQ-based photoremovable protecting groups (PPGs) is useful for the design of new quinolinyl-based PPGs for specialized applications.
Starting Page	575
Ending Page	584
Page Count	10
File Format	HTM / HTML PDF
ISSN	1474905X
Volume Number	16
Issue Number	4
Journal	Photochemical & Photobiological Sciences
DOI	10.1039/c6pp00377j
Language	English
Publisher	Royal Society of Chemistry
Access Restriction	Open
Subject Keyword	PBS Phenol Acetonitrile Proton Reaction mechanism Density functional theory Time-resolved spectroscopy Solvent Photochemistry
Content Type	Text
Resource Type	Article
Subject	Physical and Theoretical Chemistry

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