Ultrafast excited-state proton transfer in 1-naphthol

Webb, S. P.; Yeh, Sung-Wei; Philips, Laura A.; Tolbert, Margaret A.; Clark, J. H.

doi:10.1021/ja00335a093

Cited by 60 publications

(54 citation statements)

References 8 publications

(9 reference statements)

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“…13,25 The neutral emission of 1-naphthol in water is too low to be observed due to the extremely short lifetime. On addition of BSA, the peak of neutral emission emerged with a maximum at 354 nm ( [BSA] ) 1) and that of the anion form was also enhanced.…”

Section: Resultsmentioning

confidence: 99%

Binding of the Environmental Pollutant Naphthol to Bovine Serum Albumin

Guan

et al. 2007

Biomacromolecules

137

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The interactions between naphthol and bovine serum albumin (BSA) were investigated by spectroscopy. Our results prove the formation of complex between naphthol and BSA. Hydrophobic interaction dominates in the association reaction. The isomers stack with the aromatic residues in their binding sites with different geometries. Effects of BSA on the excited-state proton transfer and fluorescence spectra of the isomers indicate the different characters of their binding sites. 1-Naphthol inserts deeply into a hydrophobic cavity whereas 2-naphthol is in a basic environment on the surface of BSA. Naphthol statically quenches the fluorescence of BSA in a concentration-dependent manner positively deviating from the linear Stern-Volmer equation. Naphthol binds near Trp-134 in the subdomain IA of the native BSA and is accessible to Trp-212 when BSA is unfolded by naphthol. The folding pattern of the main chain is altered at high naphthol concentration as revealed by the change in the secondary structure. The binding of 1-naphthol is more cooperative than that of 2-naphthol. The extent of cooperativity was estimated by the Hill equation.

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Section: Resultsmentioning

confidence: 99%

Binding of the Environmental Pollutant Naphthol to Bovine Serum Albumin

Guan

et al. 2007

Biomacromolecules

137

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“…9,18,19 This shows that the deprotonation of 1-naphthol is slowed by a factor of 20 on binding to CTAB. The lifetime of the decay of the anion emission is found to be 19 ( 0.5 ns which is nearly two times longer than the lifetime of the anion in water (8 ns).…”

Section: Steady-state Emission Spectramentioning

confidence: 92%

Excited-State Proton Transfer of 1-Naphthol in Micelles

1998

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The fast deprotonation of 1-naphthol, which occurs in 35 ps in aqueous solution, is studied in neutral (triton X 100, reduced, TX-100R), cationic (cetyl trimethylammonium bromide, CTAB), and anionic (sodium dodecyl sulfate, SDS) micelles. Drastically different effects on the proton transfer process and the relative emission intensities of the neutral form (360 nm) and the anion (460 nm) are observed in the three micelles. The intensities of the anion and the neutral emission of 1-naphthol exhibit a break around the reported critical micellar concentration (cmc) of the three micelles. Above cmc, intensity of the neutral emission is enhanced by a factor of nearly 90, 66, and 20 in 20 mM TX-100R, 200 mM SDS, and 96 mM CTAB, respectively. The anion emission is enhanced for CTAB and TX-100R, while for SDS its intensity decreases, compared to water. In CTAB, the rise time of the 460 nm emission (600 ( 100 ps) is similar to the lifetime of decay at 360 nm. However, for TX-100R and SDS, the rise time of the anion emission (at 460 nm) is found to be faster than the decay of the neutral emission (at 360 nm). This indicates that in TX-100R and SDS, there is no parental relation between the normal and the anion emission and they originate from the probe, 1-naphthol molecules, at distinctly different locations. The rise times at 460 nm are 1.8 ( 0.1 ns and 600 ( 100 ps for TX-100R and SDS, respectively, while the corresponding decay times at 360 nm are 2.5 ( 0.1 ns and 1.8 ( 0.1 ns.

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“…Previous studies indicated that the frequency of the C-O stretch mode appears in the 1400-1600 cm À1 range assigned to a ππ* nature triplet state and in the 1200-1400 cm À1 region as a typical nπ* nature triplet state. [29][30][31][32][33] As illustrated above, the C-O stretching frequency for 3 SPF is located at 1413 cm À1 , and this indicates the 3 SPF possesses a ππ* electronic configuration. Inspection of Fig.…”

Section: Nanosecond-tr 3 Study In Mecnmentioning

confidence: 99%

Time‐resolved spectroscopic and density functional theory investigation of the photochemistry of suprofen

Zhu

Xue

et al. 2014

J Raman Spectroscopy

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The photochemistry of suprofen (SPF) was investigated by femtosecond transient absorption (fs-TA), resonance Raman (RR) and nanosecond time-resolved resonance Raman (ns-TR 3 ) spectroscopic methods to gain additional information so as to better elucidate the possible photochemical reaction mechanism of suprofen in several different solvents. In neat acetonitrile (MeCN), the fs-TA and ns-TR 3 experimental data indicated that the lowest lying excited singlet state S 1 (nπ*) underwent an efficient intersystem crossing process (ISC) to the excited triplet state T 3 (ππ*), followed by an internal conversion (IC) process to T 1 (ππ*). In the aqueous solution, a triplet biradical species ( 3 ETK-1) was obtained as the product of a decarboxylation process from triplet suprofen anion ( 3 SPF À ) and the reaction rate of the decarboxylation process was determined by the concentration of H 2 O. A protonation process for 3 ETK-1 leads to formation of a neutral species ( 3 ETK-3) that was directly observed by ns-TR 3 spectra, then this 3 ETK-3 species decayed via ISC process to generate final product.

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Ultrafast excited-state proton transfer in 1-naphthol

Cited by 60 publications

References 8 publications

Binding of the Environmental Pollutant Naphthol to Bovine Serum Albumin

Binding of the Environmental Pollutant Naphthol to Bovine Serum Albumin

Excited-State Proton Transfer of 1-Naphthol in Micelles

Time‐resolved spectroscopic and density functional theory investigation of the photochemistry of suprofen

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