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

TitleObservation of excited state proton transfer reactions in 2-phenylphenol and 2-phenyl-1-naphthol and formation of quinone methide species
Authors
Issue Date2015
PublisherRoyal Society of Chemistry. The Journal's web site is located at http://www.rsc.org/pccp
Citation
Physical Chemistry Chemical Physics, 2015, v. 17 n. 14, p. 9205-9211 How to Cite?
AbstractThe 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 the absorbance of the transient species being more intense, which suggests there is more efficient production of the QM species from 4, consistent with quantum yields for deuterium exchange in the distal ring reported for these compounds.
Persistent Identifierhttp://hdl.handle.net/10722/215102
ISSN
2015 Impact Factor: 4.449
2015 SCImago Journal Rankings: 1.836

 

DC FieldValueLanguage
dc.contributor.authorMa, J-
dc.contributor.authorZhang, X-
dc.contributor.authorBasarić, N-
dc.contributor.authorWan, P-
dc.contributor.authorPhillips, DL-
dc.date.accessioned2015-08-21T12:28:01Z-
dc.date.available2015-08-21T12:28:01Z-
dc.date.issued2015-
dc.identifier.citationPhysical Chemistry Chemical Physics, 2015, v. 17 n. 14, p. 9205-9211-
dc.identifier.issn1463-9076-
dc.identifier.urihttp://hdl.handle.net/10722/215102-
dc.description.abstractThe 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 the absorbance of the transient species being more intense, which suggests there is more efficient production of the QM species from 4, consistent with quantum yields for deuterium exchange in the distal ring reported for these compounds.-
dc.languageeng-
dc.publisherRoyal Society of Chemistry. The Journal's web site is located at http://www.rsc.org/pccp-
dc.relation.ispartofPhysical Chemistry Chemical Physics-
dc.titleObservation of excited state proton transfer reactions in 2-phenylphenol and 2-phenyl-1-naphthol and formation of quinone methide species-
dc.typeArticle-
dc.identifier.emailMa, J: majiani@hku.hk-
dc.identifier.emailPhillips, DL: phillips@hku.hk-
dc.identifier.authorityPhillips, DL=rp00770-
dc.identifier.doi10.1039/C4CP05061D-
dc.identifier.pmid25760013-
dc.identifier.hkuros246420-
dc.identifier.volume17-
dc.identifier.issue14-
dc.identifier.spage9205-
dc.identifier.epage9211-
dc.publisher.placeUnited Kingdom-

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