Time-resolved spectroscopic and density functional theory investigation of the influence of the leaving group on the generation of a binol quinone methide
Quinone methides are important reactive intermediates in photobiology and photochemistry, with little known regarding the photo-induces generation of reactive quinone methides species from relevant precursors in aqueous solutions. Here, the time-resolved spectroscopy methods including the transient...
Ausführliche Beschreibung
Gespeichert in:
| Autor*in: |
Yan, Zhiping [verfasserIn] |
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| Format: |
E-Artikel |
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| Sprache: |
Englisch |
| Erschienen: |
2018transfer abstract |
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| Schlagwörter: |
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| Umfang: |
6 |
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| Übergeordnetes Werk: |
Enthalten in: Artificial neural network modelling of amido black dye sorption on iron composite nano material: Kinetics and thermodynamics studies - Ali, Imran ELSEVIER, 2017, New York, NY [u.a.] |
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| Übergeordnetes Werk: |
volume:1172 ; year:2018 ; day:15 ; month:11 ; pages:102-107 ; extent:6 |
| Links: |
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| DOI / URN: |
10.1016/j.molstruc.2017.11.012 |
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ELV043950434 |
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| 520 | |a Quinone methides are important reactive intermediates in photobiology and photochemistry, with little known regarding the photo-induces generation of reactive quinone methides species from relevant precursors in aqueous solutions. Here, the time-resolved spectroscopy methods including the transient absorption experiments and time-resolved Resonance Raman were employed to directly study the photophysics and photochemical processes of 6,6′-Bis(hydroxymethyl)-1,1′-binaphthyl-2,2′-diol (BQMP-a) in neat MeCN and 1:1 MeCN:H2O aqueous solutions. In aqueous solution, the intramolecular excited state proton transfer (ESIPT) process was observed where the water molecules help deliver the proton on the hydroxyl group to the naphthol ring within 125 ps in the singlet excited state of BQMP-a. This solvent mediated ESIPT will then lead to the leaving of the H2O group in 906 ps followed by the generation of the binol quinone methide (BQM-a) intermediate with a lifetime of 1.7 μs. As a result, the BQMP-a provides a different production rate of quinone methides compared with the 1,1′-(2,2′-Dihydroxy-1,1′-binaphthyl-6,6′-diyl) bis(N,N,N-trimethylmethanaminium) bromide system, which indicates the leaving group is an important factor in the generation of the reactive DNA alkylated intermediates. | ||
| 520 | |a Quinone methides are important reactive intermediates in photobiology and photochemistry, with little known regarding the photo-induces generation of reactive quinone methides species from relevant precursors in aqueous solutions. Here, the time-resolved spectroscopy methods including the transient absorption experiments and time-resolved Resonance Raman were employed to directly study the photophysics and photochemical processes of 6,6′-Bis(hydroxymethyl)-1,1′-binaphthyl-2,2′-diol (BQMP-a) in neat MeCN and 1:1 MeCN:H2O aqueous solutions. In aqueous solution, the intramolecular excited state proton transfer (ESIPT) process was observed where the water molecules help deliver the proton on the hydroxyl group to the naphthol ring within 125 ps in the singlet excited state of BQMP-a. This solvent mediated ESIPT will then lead to the leaving of the H2O group in 906 ps followed by the generation of the binol quinone methide (BQM-a) intermediate with a lifetime of 1.7 μs. As a result, the BQMP-a provides a different production rate of quinone methides compared with the 1,1′-(2,2′-Dihydroxy-1,1′-binaphthyl-6,6′-diyl) bis(N,N,N-trimethylmethanaminium) bromide system, which indicates the leaving group is an important factor in the generation of the reactive DNA alkylated intermediates. | ||
| 650 | 7 | |a DFT calculation |2 Elsevier | |
| 650 | 7 | |a Quinone methide |2 Elsevier | |
| 650 | 7 | |a Time-resolved spectroscopy |2 Elsevier | |
| 650 | 7 | |a Time-resolved resonance Raman |2 Elsevier | |
| 700 | 1 | |a Du, Lili |4 oth | |
| 700 | 1 | |a Lan, Xin |4 oth | |
| 700 | 1 | |a Zhang, Xiting |4 oth | |
| 700 | 1 | |a Phillips, David Lee |4 oth | |
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10.1016/j.molstruc.2017.11.012 doi GBV00000000000349.pica (DE-627)ELV043950434 (ELSEVIER)S0022-2860(17)31485-0 DE-627 ger DE-627 rakwb eng 540 VZ 35.21 bkl Yan, Zhiping verfasserin aut Time-resolved spectroscopic and density functional theory investigation of the influence of the leaving group on the generation of a binol quinone methide 2018transfer abstract 6 nicht spezifiziert zzz rdacontent nicht spezifiziert z rdamedia nicht spezifiziert zu rdacarrier Quinone methides are important reactive intermediates in photobiology and photochemistry, with little known regarding the photo-induces generation of reactive quinone methides species from relevant precursors in aqueous solutions. Here, the time-resolved spectroscopy methods including the transient absorption experiments and time-resolved Resonance Raman were employed to directly study the photophysics and photochemical processes of 6,6′-Bis(hydroxymethyl)-1,1′-binaphthyl-2,2′-diol (BQMP-a) in neat MeCN and 1:1 MeCN:H2O aqueous solutions. In aqueous solution, the intramolecular excited state proton transfer (ESIPT) process was observed where the water molecules help deliver the proton on the hydroxyl group to the naphthol ring within 125 ps in the singlet excited state of BQMP-a. This solvent mediated ESIPT will then lead to the leaving of the H2O group in 906 ps followed by the generation of the binol quinone methide (BQM-a) intermediate with a lifetime of 1.7 μs. As a result, the BQMP-a provides a different production rate of quinone methides compared with the 1,1′-(2,2′-Dihydroxy-1,1′-binaphthyl-6,6′-diyl) bis(N,N,N-trimethylmethanaminium) bromide system, which indicates the leaving group is an important factor in the generation of the reactive DNA alkylated intermediates. Quinone methides are important reactive intermediates in photobiology and photochemistry, with little known regarding the photo-induces generation of reactive quinone methides species from relevant precursors in aqueous solutions. Here, the time-resolved spectroscopy methods including the transient absorption experiments and time-resolved Resonance Raman were employed to directly study the photophysics and photochemical processes of 6,6′-Bis(hydroxymethyl)-1,1′-binaphthyl-2,2′-diol (BQMP-a) in neat MeCN and 1:1 MeCN:H2O aqueous solutions. In aqueous solution, the intramolecular excited state proton transfer (ESIPT) process was observed where the water molecules help deliver the proton on the hydroxyl group to the naphthol ring within 125 ps in the singlet excited state of BQMP-a. This solvent mediated ESIPT will then lead to the leaving of the H2O group in 906 ps followed by the generation of the binol quinone methide (BQM-a) intermediate with a lifetime of 1.7 μs. As a result, the BQMP-a provides a different production rate of quinone methides compared with the 1,1′-(2,2′-Dihydroxy-1,1′-binaphthyl-6,6′-diyl) bis(N,N,N-trimethylmethanaminium) bromide system, which indicates the leaving group is an important factor in the generation of the reactive DNA alkylated intermediates. DFT calculation Elsevier Quinone methide Elsevier Time-resolved spectroscopy Elsevier Time-resolved resonance Raman Elsevier Du, Lili oth Lan, Xin oth Zhang, Xiting oth Phillips, David Lee oth Enthalten in Elsevier Ali, Imran ELSEVIER Artificial neural network modelling of amido black dye sorption on iron composite nano material: Kinetics and thermodynamics studies 2017 New York, NY [u.a.] (DE-627)ELV005044758 volume:1172 year:2018 day:15 month:11 pages:102-107 extent:6 https://doi.org/10.1016/j.molstruc.2017.11.012 Volltext GBV_USEFLAG_U GBV_ELV SYSFLAG_U SSG-OLC-PHA 35.21 Lösungen Flüssigkeiten Physikalische Chemie VZ AR 1172 2018 15 1115 102-107 6 |
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10.1016/j.molstruc.2017.11.012 doi GBV00000000000349.pica (DE-627)ELV043950434 (ELSEVIER)S0022-2860(17)31485-0 DE-627 ger DE-627 rakwb eng 540 VZ 35.21 bkl Yan, Zhiping verfasserin aut Time-resolved spectroscopic and density functional theory investigation of the influence of the leaving group on the generation of a binol quinone methide 2018transfer abstract 6 nicht spezifiziert zzz rdacontent nicht spezifiziert z rdamedia nicht spezifiziert zu rdacarrier Quinone methides are important reactive intermediates in photobiology and photochemistry, with little known regarding the photo-induces generation of reactive quinone methides species from relevant precursors in aqueous solutions. Here, the time-resolved spectroscopy methods including the transient absorption experiments and time-resolved Resonance Raman were employed to directly study the photophysics and photochemical processes of 6,6′-Bis(hydroxymethyl)-1,1′-binaphthyl-2,2′-diol (BQMP-a) in neat MeCN and 1:1 MeCN:H2O aqueous solutions. In aqueous solution, the intramolecular excited state proton transfer (ESIPT) process was observed where the water molecules help deliver the proton on the hydroxyl group to the naphthol ring within 125 ps in the singlet excited state of BQMP-a. This solvent mediated ESIPT will then lead to the leaving of the H2O group in 906 ps followed by the generation of the binol quinone methide (BQM-a) intermediate with a lifetime of 1.7 μs. As a result, the BQMP-a provides a different production rate of quinone methides compared with the 1,1′-(2,2′-Dihydroxy-1,1′-binaphthyl-6,6′-diyl) bis(N,N,N-trimethylmethanaminium) bromide system, which indicates the leaving group is an important factor in the generation of the reactive DNA alkylated intermediates. Quinone methides are important reactive intermediates in photobiology and photochemistry, with little known regarding the photo-induces generation of reactive quinone methides species from relevant precursors in aqueous solutions. Here, the time-resolved spectroscopy methods including the transient absorption experiments and time-resolved Resonance Raman were employed to directly study the photophysics and photochemical processes of 6,6′-Bis(hydroxymethyl)-1,1′-binaphthyl-2,2′-diol (BQMP-a) in neat MeCN and 1:1 MeCN:H2O aqueous solutions. In aqueous solution, the intramolecular excited state proton transfer (ESIPT) process was observed where the water molecules help deliver the proton on the hydroxyl group to the naphthol ring within 125 ps in the singlet excited state of BQMP-a. This solvent mediated ESIPT will then lead to the leaving of the H2O group in 906 ps followed by the generation of the binol quinone methide (BQM-a) intermediate with a lifetime of 1.7 μs. As a result, the BQMP-a provides a different production rate of quinone methides compared with the 1,1′-(2,2′-Dihydroxy-1,1′-binaphthyl-6,6′-diyl) bis(N,N,N-trimethylmethanaminium) bromide system, which indicates the leaving group is an important factor in the generation of the reactive DNA alkylated intermediates. DFT calculation Elsevier Quinone methide Elsevier Time-resolved spectroscopy Elsevier Time-resolved resonance Raman Elsevier Du, Lili oth Lan, Xin oth Zhang, Xiting oth Phillips, David Lee oth Enthalten in Elsevier Ali, Imran ELSEVIER Artificial neural network modelling of amido black dye sorption on iron composite nano material: Kinetics and thermodynamics studies 2017 New York, NY [u.a.] (DE-627)ELV005044758 volume:1172 year:2018 day:15 month:11 pages:102-107 extent:6 https://doi.org/10.1016/j.molstruc.2017.11.012 Volltext GBV_USEFLAG_U GBV_ELV SYSFLAG_U SSG-OLC-PHA 35.21 Lösungen Flüssigkeiten Physikalische Chemie VZ AR 1172 2018 15 1115 102-107 6 |
| allfields_unstemmed |
10.1016/j.molstruc.2017.11.012 doi GBV00000000000349.pica (DE-627)ELV043950434 (ELSEVIER)S0022-2860(17)31485-0 DE-627 ger DE-627 rakwb eng 540 VZ 35.21 bkl Yan, Zhiping verfasserin aut Time-resolved spectroscopic and density functional theory investigation of the influence of the leaving group on the generation of a binol quinone methide 2018transfer abstract 6 nicht spezifiziert zzz rdacontent nicht spezifiziert z rdamedia nicht spezifiziert zu rdacarrier Quinone methides are important reactive intermediates in photobiology and photochemistry, with little known regarding the photo-induces generation of reactive quinone methides species from relevant precursors in aqueous solutions. Here, the time-resolved spectroscopy methods including the transient absorption experiments and time-resolved Resonance Raman were employed to directly study the photophysics and photochemical processes of 6,6′-Bis(hydroxymethyl)-1,1′-binaphthyl-2,2′-diol (BQMP-a) in neat MeCN and 1:1 MeCN:H2O aqueous solutions. In aqueous solution, the intramolecular excited state proton transfer (ESIPT) process was observed where the water molecules help deliver the proton on the hydroxyl group to the naphthol ring within 125 ps in the singlet excited state of BQMP-a. This solvent mediated ESIPT will then lead to the leaving of the H2O group in 906 ps followed by the generation of the binol quinone methide (BQM-a) intermediate with a lifetime of 1.7 μs. As a result, the BQMP-a provides a different production rate of quinone methides compared with the 1,1′-(2,2′-Dihydroxy-1,1′-binaphthyl-6,6′-diyl) bis(N,N,N-trimethylmethanaminium) bromide system, which indicates the leaving group is an important factor in the generation of the reactive DNA alkylated intermediates. Quinone methides are important reactive intermediates in photobiology and photochemistry, with little known regarding the photo-induces generation of reactive quinone methides species from relevant precursors in aqueous solutions. Here, the time-resolved spectroscopy methods including the transient absorption experiments and time-resolved Resonance Raman were employed to directly study the photophysics and photochemical processes of 6,6′-Bis(hydroxymethyl)-1,1′-binaphthyl-2,2′-diol (BQMP-a) in neat MeCN and 1:1 MeCN:H2O aqueous solutions. In aqueous solution, the intramolecular excited state proton transfer (ESIPT) process was observed where the water molecules help deliver the proton on the hydroxyl group to the naphthol ring within 125 ps in the singlet excited state of BQMP-a. This solvent mediated ESIPT will then lead to the leaving of the H2O group in 906 ps followed by the generation of the binol quinone methide (BQM-a) intermediate with a lifetime of 1.7 μs. As a result, the BQMP-a provides a different production rate of quinone methides compared with the 1,1′-(2,2′-Dihydroxy-1,1′-binaphthyl-6,6′-diyl) bis(N,N,N-trimethylmethanaminium) bromide system, which indicates the leaving group is an important factor in the generation of the reactive DNA alkylated intermediates. DFT calculation Elsevier Quinone methide Elsevier Time-resolved spectroscopy Elsevier Time-resolved resonance Raman Elsevier Du, Lili oth Lan, Xin oth Zhang, Xiting oth Phillips, David Lee oth Enthalten in Elsevier Ali, Imran ELSEVIER Artificial neural network modelling of amido black dye sorption on iron composite nano material: Kinetics and thermodynamics studies 2017 New York, NY [u.a.] (DE-627)ELV005044758 volume:1172 year:2018 day:15 month:11 pages:102-107 extent:6 https://doi.org/10.1016/j.molstruc.2017.11.012 Volltext GBV_USEFLAG_U GBV_ELV SYSFLAG_U SSG-OLC-PHA 35.21 Lösungen Flüssigkeiten Physikalische Chemie VZ AR 1172 2018 15 1115 102-107 6 |
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10.1016/j.molstruc.2017.11.012 doi GBV00000000000349.pica (DE-627)ELV043950434 (ELSEVIER)S0022-2860(17)31485-0 DE-627 ger DE-627 rakwb eng 540 VZ 35.21 bkl Yan, Zhiping verfasserin aut Time-resolved spectroscopic and density functional theory investigation of the influence of the leaving group on the generation of a binol quinone methide 2018transfer abstract 6 nicht spezifiziert zzz rdacontent nicht spezifiziert z rdamedia nicht spezifiziert zu rdacarrier Quinone methides are important reactive intermediates in photobiology and photochemistry, with little known regarding the photo-induces generation of reactive quinone methides species from relevant precursors in aqueous solutions. Here, the time-resolved spectroscopy methods including the transient absorption experiments and time-resolved Resonance Raman were employed to directly study the photophysics and photochemical processes of 6,6′-Bis(hydroxymethyl)-1,1′-binaphthyl-2,2′-diol (BQMP-a) in neat MeCN and 1:1 MeCN:H2O aqueous solutions. In aqueous solution, the intramolecular excited state proton transfer (ESIPT) process was observed where the water molecules help deliver the proton on the hydroxyl group to the naphthol ring within 125 ps in the singlet excited state of BQMP-a. This solvent mediated ESIPT will then lead to the leaving of the H2O group in 906 ps followed by the generation of the binol quinone methide (BQM-a) intermediate with a lifetime of 1.7 μs. As a result, the BQMP-a provides a different production rate of quinone methides compared with the 1,1′-(2,2′-Dihydroxy-1,1′-binaphthyl-6,6′-diyl) bis(N,N,N-trimethylmethanaminium) bromide system, which indicates the leaving group is an important factor in the generation of the reactive DNA alkylated intermediates. Quinone methides are important reactive intermediates in photobiology and photochemistry, with little known regarding the photo-induces generation of reactive quinone methides species from relevant precursors in aqueous solutions. Here, the time-resolved spectroscopy methods including the transient absorption experiments and time-resolved Resonance Raman were employed to directly study the photophysics and photochemical processes of 6,6′-Bis(hydroxymethyl)-1,1′-binaphthyl-2,2′-diol (BQMP-a) in neat MeCN and 1:1 MeCN:H2O aqueous solutions. In aqueous solution, the intramolecular excited state proton transfer (ESIPT) process was observed where the water molecules help deliver the proton on the hydroxyl group to the naphthol ring within 125 ps in the singlet excited state of BQMP-a. This solvent mediated ESIPT will then lead to the leaving of the H2O group in 906 ps followed by the generation of the binol quinone methide (BQM-a) intermediate with a lifetime of 1.7 μs. As a result, the BQMP-a provides a different production rate of quinone methides compared with the 1,1′-(2,2′-Dihydroxy-1,1′-binaphthyl-6,6′-diyl) bis(N,N,N-trimethylmethanaminium) bromide system, which indicates the leaving group is an important factor in the generation of the reactive DNA alkylated intermediates. DFT calculation Elsevier Quinone methide Elsevier Time-resolved spectroscopy Elsevier Time-resolved resonance Raman Elsevier Du, Lili oth Lan, Xin oth Zhang, Xiting oth Phillips, David Lee oth Enthalten in Elsevier Ali, Imran ELSEVIER Artificial neural network modelling of amido black dye sorption on iron composite nano material: Kinetics and thermodynamics studies 2017 New York, NY [u.a.] (DE-627)ELV005044758 volume:1172 year:2018 day:15 month:11 pages:102-107 extent:6 https://doi.org/10.1016/j.molstruc.2017.11.012 Volltext GBV_USEFLAG_U GBV_ELV SYSFLAG_U SSG-OLC-PHA 35.21 Lösungen Flüssigkeiten Physikalische Chemie VZ AR 1172 2018 15 1115 102-107 6 |
| allfieldsSound |
10.1016/j.molstruc.2017.11.012 doi GBV00000000000349.pica (DE-627)ELV043950434 (ELSEVIER)S0022-2860(17)31485-0 DE-627 ger DE-627 rakwb eng 540 VZ 35.21 bkl Yan, Zhiping verfasserin aut Time-resolved spectroscopic and density functional theory investigation of the influence of the leaving group on the generation of a binol quinone methide 2018transfer abstract 6 nicht spezifiziert zzz rdacontent nicht spezifiziert z rdamedia nicht spezifiziert zu rdacarrier Quinone methides are important reactive intermediates in photobiology and photochemistry, with little known regarding the photo-induces generation of reactive quinone methides species from relevant precursors in aqueous solutions. Here, the time-resolved spectroscopy methods including the transient absorption experiments and time-resolved Resonance Raman were employed to directly study the photophysics and photochemical processes of 6,6′-Bis(hydroxymethyl)-1,1′-binaphthyl-2,2′-diol (BQMP-a) in neat MeCN and 1:1 MeCN:H2O aqueous solutions. In aqueous solution, the intramolecular excited state proton transfer (ESIPT) process was observed where the water molecules help deliver the proton on the hydroxyl group to the naphthol ring within 125 ps in the singlet excited state of BQMP-a. This solvent mediated ESIPT will then lead to the leaving of the H2O group in 906 ps followed by the generation of the binol quinone methide (BQM-a) intermediate with a lifetime of 1.7 μs. As a result, the BQMP-a provides a different production rate of quinone methides compared with the 1,1′-(2,2′-Dihydroxy-1,1′-binaphthyl-6,6′-diyl) bis(N,N,N-trimethylmethanaminium) bromide system, which indicates the leaving group is an important factor in the generation of the reactive DNA alkylated intermediates. Quinone methides are important reactive intermediates in photobiology and photochemistry, with little known regarding the photo-induces generation of reactive quinone methides species from relevant precursors in aqueous solutions. Here, the time-resolved spectroscopy methods including the transient absorption experiments and time-resolved Resonance Raman were employed to directly study the photophysics and photochemical processes of 6,6′-Bis(hydroxymethyl)-1,1′-binaphthyl-2,2′-diol (BQMP-a) in neat MeCN and 1:1 MeCN:H2O aqueous solutions. In aqueous solution, the intramolecular excited state proton transfer (ESIPT) process was observed where the water molecules help deliver the proton on the hydroxyl group to the naphthol ring within 125 ps in the singlet excited state of BQMP-a. This solvent mediated ESIPT will then lead to the leaving of the H2O group in 906 ps followed by the generation of the binol quinone methide (BQM-a) intermediate with a lifetime of 1.7 μs. As a result, the BQMP-a provides a different production rate of quinone methides compared with the 1,1′-(2,2′-Dihydroxy-1,1′-binaphthyl-6,6′-diyl) bis(N,N,N-trimethylmethanaminium) bromide system, which indicates the leaving group is an important factor in the generation of the reactive DNA alkylated intermediates. DFT calculation Elsevier Quinone methide Elsevier Time-resolved spectroscopy Elsevier Time-resolved resonance Raman Elsevier Du, Lili oth Lan, Xin oth Zhang, Xiting oth Phillips, David Lee oth Enthalten in Elsevier Ali, Imran ELSEVIER Artificial neural network modelling of amido black dye sorption on iron composite nano material: Kinetics and thermodynamics studies 2017 New York, NY [u.a.] (DE-627)ELV005044758 volume:1172 year:2018 day:15 month:11 pages:102-107 extent:6 https://doi.org/10.1016/j.molstruc.2017.11.012 Volltext GBV_USEFLAG_U GBV_ELV SYSFLAG_U SSG-OLC-PHA 35.21 Lösungen Flüssigkeiten Physikalische Chemie VZ AR 1172 2018 15 1115 102-107 6 |
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Enthalten in Artificial neural network modelling of amido black dye sorption on iron composite nano material: Kinetics and thermodynamics studies New York, NY [u.a.] volume:1172 year:2018 day:15 month:11 pages:102-107 extent:6 |
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Enthalten in Artificial neural network modelling of amido black dye sorption on iron composite nano material: Kinetics and thermodynamics studies New York, NY [u.a.] volume:1172 year:2018 day:15 month:11 pages:102-107 extent:6 |
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Artificial neural network modelling of amido black dye sorption on iron composite nano material: Kinetics and thermodynamics studies |
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time-resolved spectroscopic and density functional theory investigation of the influence of the leaving group on the generation of a binol quinone methide |
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Time-resolved spectroscopic and density functional theory investigation of the influence of the leaving group on the generation of a binol quinone methide |
| abstract |
Quinone methides are important reactive intermediates in photobiology and photochemistry, with little known regarding the photo-induces generation of reactive quinone methides species from relevant precursors in aqueous solutions. Here, the time-resolved spectroscopy methods including the transient absorption experiments and time-resolved Resonance Raman were employed to directly study the photophysics and photochemical processes of 6,6′-Bis(hydroxymethyl)-1,1′-binaphthyl-2,2′-diol (BQMP-a) in neat MeCN and 1:1 MeCN:H2O aqueous solutions. In aqueous solution, the intramolecular excited state proton transfer (ESIPT) process was observed where the water molecules help deliver the proton on the hydroxyl group to the naphthol ring within 125 ps in the singlet excited state of BQMP-a. This solvent mediated ESIPT will then lead to the leaving of the H2O group in 906 ps followed by the generation of the binol quinone methide (BQM-a) intermediate with a lifetime of 1.7 μs. As a result, the BQMP-a provides a different production rate of quinone methides compared with the 1,1′-(2,2′-Dihydroxy-1,1′-binaphthyl-6,6′-diyl) bis(N,N,N-trimethylmethanaminium) bromide system, which indicates the leaving group is an important factor in the generation of the reactive DNA alkylated intermediates. |
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Quinone methides are important reactive intermediates in photobiology and photochemistry, with little known regarding the photo-induces generation of reactive quinone methides species from relevant precursors in aqueous solutions. Here, the time-resolved spectroscopy methods including the transient absorption experiments and time-resolved Resonance Raman were employed to directly study the photophysics and photochemical processes of 6,6′-Bis(hydroxymethyl)-1,1′-binaphthyl-2,2′-diol (BQMP-a) in neat MeCN and 1:1 MeCN:H2O aqueous solutions. In aqueous solution, the intramolecular excited state proton transfer (ESIPT) process was observed where the water molecules help deliver the proton on the hydroxyl group to the naphthol ring within 125 ps in the singlet excited state of BQMP-a. This solvent mediated ESIPT will then lead to the leaving of the H2O group in 906 ps followed by the generation of the binol quinone methide (BQM-a) intermediate with a lifetime of 1.7 μs. As a result, the BQMP-a provides a different production rate of quinone methides compared with the 1,1′-(2,2′-Dihydroxy-1,1′-binaphthyl-6,6′-diyl) bis(N,N,N-trimethylmethanaminium) bromide system, which indicates the leaving group is an important factor in the generation of the reactive DNA alkylated intermediates. |
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Quinone methides are important reactive intermediates in photobiology and photochemistry, with little known regarding the photo-induces generation of reactive quinone methides species from relevant precursors in aqueous solutions. Here, the time-resolved spectroscopy methods including the transient absorption experiments and time-resolved Resonance Raman were employed to directly study the photophysics and photochemical processes of 6,6′-Bis(hydroxymethyl)-1,1′-binaphthyl-2,2′-diol (BQMP-a) in neat MeCN and 1:1 MeCN:H2O aqueous solutions. In aqueous solution, the intramolecular excited state proton transfer (ESIPT) process was observed where the water molecules help deliver the proton on the hydroxyl group to the naphthol ring within 125 ps in the singlet excited state of BQMP-a. This solvent mediated ESIPT will then lead to the leaving of the H2O group in 906 ps followed by the generation of the binol quinone methide (BQM-a) intermediate with a lifetime of 1.7 μs. As a result, the BQMP-a provides a different production rate of quinone methides compared with the 1,1′-(2,2′-Dihydroxy-1,1′-binaphthyl-6,6′-diyl) bis(N,N,N-trimethylmethanaminium) bromide system, which indicates the leaving group is an important factor in the generation of the reactive DNA alkylated intermediates. |
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Time-resolved spectroscopic and density functional theory investigation of the influence of the leaving group on the generation of a binol quinone methide |
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