Observation of excited state proton transfer reactions in 2-phenylphenol and 2-phenyl-1-naphthol and formation of quinone methide species

Physical Chemistry Chemical Physics : PCCP
Jiani MaDavid Lee Phillips

Abstract

The excited state intramolecular proton transfer (ESIPT) reactions from a phenol (naphthol) to a carbon atom in the adjacent aromatic ring of 2-phenylphenol (1) and 2-phenyl-1-naphthol (4) are prototypical examples of intramolecular proton transfer not mediated by solvent molecules. Femtosecond time-resolved transient absorption (fs-TA) studies are conducted for the first time to directly probe the formation of quinone methide (QM) species generated from the ESIPT pathways of 1 and 4. Steady-state absorption experiments demonstrated 1 exists mainly in its non-deprotonated form in neat MeCN and in water-MeCN solutions. Observation of the phenolate form in water-containing solution (MeCN-H2O, 1 : 1, v : v) in fluorescence spectra demonstrates the occurrence of an ESPT reaction between 1 and the surrounding water molecules. In neat MeCN a transient species that absorbs around 520 nm was detected in fs-TA spectra and was assigned to the QM species formed by ESIPT to the 2'-position. This transient signal is strengthened in cyclohexane. In a water-MeCN solution, an additional transient species assigned to the QM species at the 4'-position of 1 was also detected that absorbs around 485 nm. Similar results for 4 were observed, with th...Continue Reading

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Citations

Oct 27, 2015·The Journal of Organic Chemistry·Matthew LukemanYu-Hsuan Wang
Apr 2, 2016·The Journal of Organic Chemistry·Filippo DoriaMauro Freccero
Apr 21, 2018·Chemistry : a European Journal·Đani ŠkalameraNikola Basarić
Aug 28, 2020·The Journal of Organic Chemistry·Xiting ZhangDavid Lee Phillips
Apr 10, 2019·The Journal of Physical Chemistry. a·James N BullEvan J Bieske

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