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Photoinduced excited state intramolecular proton transfer of 2-(2′-hydroxyphenyl)phenanthro[9,10-d]oxazole: A comprehensive theoretical study

Paper ID Volume ID Publish Year Pages File Format Full-Text
26131 43936 2014 6 PDF Available
Title
Photoinduced excited state intramolecular proton transfer of 2-(2′-hydroxyphenyl)phenanthro[9,10-d]oxazole: A comprehensive theoretical study
Abstract

•The geometrical and spectral properties of HPO are investigated.•Both excited- and ground-state PESs are explored for elucidation of ESIPT.•The overall scenario for ESIPT and possible mechanism for DF are discussed.

To gain an in-depth knowledge on the enol–keto photoisomerization of an oxazole derivative, namely, 2-(2′-hydroxyphenyl)phenanthro[9,10-d]oxazole (HPO), a thorough theoretical investigation was performed on the geometrical and electronic spectroscopic properties. The present results suggest that the bond length exclusively dominates in the photoinduced process with all involved critical points keeping planar geometries. The predicted absorptions centered at 3.82 and 3.07 eV account for experimental bands at 3.61 and 3.42 eV corresponding to enol and keto forms, respectively. Orbital analysis shows that both absorption and emission bands in the title molecule essentially stem from HOMO to LUMO with typical ππ* transition character. Furthermore, both the ground- and excited-state energy profiles after photo-excitation were explored for exhaustive elucidation of the excited state intramolecular proton transfer (ESIPT). In addition, the delayed fluorescence (DF) behavior at low temperature of 77 K in experiment was tentatively attributed to triplet–triplet annihilation (TTA).

Graphical abstractScheme of the photoinduced decay mechanism suggested by the present quantum-chemical calculations.Figure optionsDownload full-size imageDownload as PowerPoint slide

Keywords
Excited state intramolecular proton transfer; Ab initio; Tautomerization; Surface crossing
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Photoinduced excited state intramolecular proton transfer of 2-(2′-hydroxyphenyl)phenanthro[9,10-d]oxazole: A comprehensive theoretical study
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Publisher
Database: Elsevier - ScienceDirect
Journal: Journal of Photochemistry and Photobiology A: Chemistry - Volume 294, 15 November 2014, Pages 14–19
Authors
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Subjects
Physical Sciences and Engineering Chemical Engineering Bioengineering
Get Full-Text Now
Don't Miss Today's Special Offer
Price was $35.95
You save - $31
Price after discount Only $4.95
100% Money Back Guarantee
Full-text PDF Download
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Any Questions? feel free to contact us