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Article: Time-Resolved Spectroscopic and Density Functional Theory Investigation of the Photogeneration of a Bifunctional Quinone Methide in Neutral and Basic Aqueous Solutions
Title | Time-Resolved Spectroscopic and Density Functional Theory Investigation of the Photogeneration of a Bifunctional Quinone Methide in Neutral and Basic Aqueous Solutions |
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Authors | |
Keywords | Bifunctional quinone methides DFT calculation E1bc elimination reaction Time-resolved resonance Raman |
Issue Date | 2018 |
Publisher | Molecular Diversity Preservation International. The Journal's web site is located at http://www.mdpi.org/molecules |
Citation | Molecules, 2018, v. 23 n. 12, p. article no. 3102 How to Cite? |
Abstract | Binol quinone methides (BQMs) can be generated from 1,1-(2,2-dihydroxy-1,1-binaphthyl-6,6-diyl)bis(N,N,N-trimethylmethanamiuium) bromide (BQMP-b) in a 1:1 MeCN:H2O mixed solution via a ground state intramolecular proton transfer (GSIPT), as mentioned in our previously reported studies. Here, the photoreaction of BQMP-b in neutral and basic aqueous solution (pH = 7, 10, 12) was investigated to explore the possible mechanisms and the key intermediates produced in the process of the photoreaction and to examine whether they are different from those in a neutral mild-mixed MeCN:H2O solution. The studies were conducted using femtosecond transient absorption (fs-TA), nanosecond transient absorption (ns-TA), and nanosecond time-resolved resonance Raman spectroscopy (ns-TR3) in conjunction with results from density functional theory (DFT) computations. The results showed that BQMP-b was deprotonated initially and produced BQMs species more effectively through an E1bc elimination reaction in a strong basic aqueous condition (pH = 12), which differed from the reaction pathway that took place in the solution with pH = 7 or 10. A related single naphthol ring molecule 1-(6-hydroxynaphthalen-2-yl)-N,N,N-trimethylmethanaminium bromide (QMP-b) that did not contain a second naphthol ring was also investigated. The related reaction mechanisms are elucidated in this work, and it is briefly discussed how the mechanisms vary as a function of aqueous solution pH conditions. |
Persistent Identifier | http://hdl.handle.net/10722/273835 |
ISSN | 2023 Impact Factor: 4.2 2023 SCImago Journal Rankings: 0.744 |
ISI Accession Number ID |
DC Field | Value | Language |
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dc.contributor.author | Yan, Z | - |
dc.contributor.author | Du, L | - |
dc.contributor.author | Lan, X | - |
dc.contributor.author | Li, Y | - |
dc.contributor.author | Wang, W | - |
dc.contributor.author | Phillips, DL | - |
dc.date.accessioned | 2019-08-18T14:49:31Z | - |
dc.date.available | 2019-08-18T14:49:31Z | - |
dc.date.issued | 2018 | - |
dc.identifier.citation | Molecules, 2018, v. 23 n. 12, p. article no. 3102 | - |
dc.identifier.issn | 1420-3049 | - |
dc.identifier.uri | http://hdl.handle.net/10722/273835 | - |
dc.description.abstract | Binol quinone methides (BQMs) can be generated from 1,1-(2,2-dihydroxy-1,1-binaphthyl-6,6-diyl)bis(N,N,N-trimethylmethanamiuium) bromide (BQMP-b) in a 1:1 MeCN:H2O mixed solution via a ground state intramolecular proton transfer (GSIPT), as mentioned in our previously reported studies. Here, the photoreaction of BQMP-b in neutral and basic aqueous solution (pH = 7, 10, 12) was investigated to explore the possible mechanisms and the key intermediates produced in the process of the photoreaction and to examine whether they are different from those in a neutral mild-mixed MeCN:H2O solution. The studies were conducted using femtosecond transient absorption (fs-TA), nanosecond transient absorption (ns-TA), and nanosecond time-resolved resonance Raman spectroscopy (ns-TR3) in conjunction with results from density functional theory (DFT) computations. The results showed that BQMP-b was deprotonated initially and produced BQMs species more effectively through an E1bc elimination reaction in a strong basic aqueous condition (pH = 12), which differed from the reaction pathway that took place in the solution with pH = 7 or 10. A related single naphthol ring molecule 1-(6-hydroxynaphthalen-2-yl)-N,N,N-trimethylmethanaminium bromide (QMP-b) that did not contain a second naphthol ring was also investigated. The related reaction mechanisms are elucidated in this work, and it is briefly discussed how the mechanisms vary as a function of aqueous solution pH conditions. | - |
dc.language | eng | - |
dc.publisher | Molecular Diversity Preservation International. The Journal's web site is located at http://www.mdpi.org/molecules | - |
dc.relation.ispartof | Molecules | - |
dc.rights | This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License. | - |
dc.subject | Bifunctional quinone methides | - |
dc.subject | DFT calculation | - |
dc.subject | E1bc elimination reaction | - |
dc.subject | Time-resolved resonance Raman | - |
dc.title | Time-Resolved Spectroscopic and Density Functional Theory Investigation of the Photogeneration of a Bifunctional Quinone Methide in Neutral and Basic Aqueous Solutions | - |
dc.type | Article | - |
dc.identifier.email | Du, L: ailleen@hku.hk | - |
dc.identifier.email | Phillips, DL: phillips@hku.hk | - |
dc.identifier.authority | Phillips, DL=rp00770 | - |
dc.description.nature | published_or_final_version | - |
dc.identifier.doi | 10.3390/molecules23123102 | - |
dc.identifier.pmid | 30486443 | - |
dc.identifier.scopus | eid_2-s2.0-85057505300 | - |
dc.identifier.hkuros | 300967 | - |
dc.identifier.volume | 23 | - |
dc.identifier.issue | 12 | - |
dc.identifier.spage | article no. 3102 | - |
dc.identifier.epage | article no. 3102 | - |
dc.identifier.isi | WOS:000454523000052 | - |
dc.publisher.place | Switzerland | - |
dc.identifier.issnl | 1420-3049 | - |