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- Publisher Website: 10.1039/C9CP01227C
- Scopus: eid_2-s2.0-85068817525
- PMID: 31187831
- WOS: WOS:000477969700013
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Article: The solvent effect on the photodeprotection of anthraquinone protected carboxylic acid unravelled by time-resolved spectroscopic studies
Title | The solvent effect on the photodeprotection of anthraquinone protected carboxylic acid unravelled by time-resolved spectroscopic studies |
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Authors | |
Keywords | Aromatic compounds Atoms Chromophores Density functional theory Design for testability |
Issue Date | 2019 |
Publisher | Royal Society of Chemistry. The Journal's web site is located at http://www.rsc.org/pccp |
Citation | Physical Chemistry Chemical Physics, 2019, v. 21 n. 27, p. 14598-14604 How to Cite? |
Abstract | Time-resolved spectroscopy studies coupled with the results from density functional theory (DFT) computations were utilized to unravel the photodeprotection reaction mechanism(s) of AQ protected p-methoxybenzoic acid (1) and its influence on the solvent was examined. It has been found that in aprotic organic solvents such as acetonitrile only the triplet state species was seen, whereas a hydrogen atom transfer (HAT) reaction takes place in isopropanol (IPA) to yield the aromatic ketyl radical species for 1. Compound 1 undergoes HAT and a proton transfer process sequentially to accomplish the release of the leaving group in protic organic solvent MeOH and MeOH–H2O solutions and photodeprotection is more favourable in the latter solution due to the stronger proton mediation ability of the water molecules and this system also facilitates the potential application of 1 in biological systems. Although the released acid from photodeprotection reaction can also be seen in another aqueous solvent system of THF–H2O, the by-product of the AQ chromophore undergoes side recombination reaction, which means this the solvent is not preferred for the photodeprotection process. This mechanistic work will help in the future design and development of AQ-PPGs for particular applications. |
Persistent Identifier | http://hdl.handle.net/10722/286177 |
ISSN | 2021 Impact Factor: 3.945 2020 SCImago Journal Rankings: 1.053 |
ISI Accession Number ID |
DC Field | Value | Language |
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dc.contributor.author | Guo, Y | - |
dc.contributor.author | Song, Q | - |
dc.contributor.author | Xu, T | - |
dc.contributor.author | Ma, J | - |
dc.contributor.author | Phillips, DL | - |
dc.date.accessioned | 2020-08-31T07:00:13Z | - |
dc.date.available | 2020-08-31T07:00:13Z | - |
dc.date.issued | 2019 | - |
dc.identifier.citation | Physical Chemistry Chemical Physics, 2019, v. 21 n. 27, p. 14598-14604 | - |
dc.identifier.issn | 1463-9076 | - |
dc.identifier.uri | http://hdl.handle.net/10722/286177 | - |
dc.description.abstract | Time-resolved spectroscopy studies coupled with the results from density functional theory (DFT) computations were utilized to unravel the photodeprotection reaction mechanism(s) of AQ protected p-methoxybenzoic acid (1) and its influence on the solvent was examined. It has been found that in aprotic organic solvents such as acetonitrile only the triplet state species was seen, whereas a hydrogen atom transfer (HAT) reaction takes place in isopropanol (IPA) to yield the aromatic ketyl radical species for 1. Compound 1 undergoes HAT and a proton transfer process sequentially to accomplish the release of the leaving group in protic organic solvent MeOH and MeOH–H2O solutions and photodeprotection is more favourable in the latter solution due to the stronger proton mediation ability of the water molecules and this system also facilitates the potential application of 1 in biological systems. Although the released acid from photodeprotection reaction can also be seen in another aqueous solvent system of THF–H2O, the by-product of the AQ chromophore undergoes side recombination reaction, which means this the solvent is not preferred for the photodeprotection process. This mechanistic work will help in the future design and development of AQ-PPGs for particular applications. | - |
dc.language | eng | - |
dc.publisher | Royal Society of Chemistry. The Journal's web site is located at http://www.rsc.org/pccp | - |
dc.relation.ispartof | Physical Chemistry Chemical Physics | - |
dc.subject | Aromatic compounds | - |
dc.subject | Atoms | - |
dc.subject | Chromophores | - |
dc.subject | Density functional theory | - |
dc.subject | Design for testability | - |
dc.title | The solvent effect on the photodeprotection of anthraquinone protected carboxylic acid unravelled by time-resolved spectroscopic studies | - |
dc.type | Article | - |
dc.identifier.email | Phillips, DL: phillips@hku.hk | - |
dc.identifier.authority | Phillips, DL=rp00770 | - |
dc.description.nature | link_to_subscribed_fulltext | - |
dc.identifier.doi | 10.1039/C9CP01227C | - |
dc.identifier.pmid | 31187831 | - |
dc.identifier.scopus | eid_2-s2.0-85068817525 | - |
dc.identifier.hkuros | 313839 | - |
dc.identifier.volume | 21 | - |
dc.identifier.issue | 27 | - |
dc.identifier.spage | 14598 | - |
dc.identifier.epage | 14604 | - |
dc.identifier.isi | WOS:000477969700013 | - |
dc.publisher.place | United Kingdom | - |
dc.identifier.issnl | 1463-9076 | - |