Acid-base properties of 1-naphthol. Proton-induced fluorescence quenching

Harris, Chris; Selinger, B. K.

doi:10.1021/j100448a016

Cited by 108 publications

(58 citation statements)

References 3 publications

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“…Deprotonation occurs during the excited state lifetime of the molecule. This phenomenon correlates to the widely studied photophysics of 2-Naphthol [25,[67][68][69][70][71] where the molecule undergoes the ESPT process at high pH conditions, revealing emission of the Naptholate anion around 410 nm [67]. Observation of the emissions from both the deprotonated NpTP and NpTP-F − hinted at the fact that the excited state reaction is partially completed during the excited state lifetime [67].…”

Section: Absorption and Fluorescence Studiessupporting

confidence: 75%

Nuclear Magnetic Resonance Spectroscopy Investigations of Naphthalene-Based 1,2,3-Triazole Systems for Anion Sensing

et al. 2018

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Detailed Nuclear Magnetic Resonance (NMR) spectroscopy investigations on a novel naphthalene-substituted 1,2,3-triazole-based fluorescence sensor provided evidence for the "turn-on" detection of anions. The one-step, facile synthesis of the sensors was implemented using the "Click chemistry" approach in good yield. When investigated for selectivity and sensitivity against a series of anions (F − , Cl − , Br − , I − , H 2 PO 4 − , ClO 4 − , OAc − , and BF 4 − ), the sensor displayed the strongest fluorometric response for the fluoride anion. NMR and fluorescence spectroscopic studies validate a 1:1 binding stoichiometry between the sensor and the fluoride anion. Single crystal X-ray diffraction evidence revealed the structure of the sensor in the solid state.

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Section: Absorption and Fluorescence Studiessupporting

confidence: 75%

Nuclear Magnetic Resonance Spectroscopy Investigations of Naphthalene-Based 1,2,3-Triazole Systems for Anion Sensing

et al. 2018

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“…(1)), i.e., to the right in the region of DPEOH. A similar kind of behavior pK a has been observed for naphthols [1,2] 9-phenanthrol [5] and 3-hydroxybiphenyl [6].…”

Section: Effect Of Phsupporting

confidence: 76%

“…It has been observed that the fluorescence of neutral naphthols is quenched diabatically by H ϩ at a pH approximately between 0 and 1. Depending upon the lifetimes of the acid-base species as well as other rate constants the intersection of the two curves correspond to excited state equilibrium constant ( ) for 1-naph-* pK a thol [2] and ground state equilibrium constant (pK ) a for 2-naphthol [1]. In the case of 9-phenanthrol [5] no fluorescence quenching is observed and the deactivation of the excited state is only due to proton transfer.…”

Section: Introductionmentioning

confidence: 99%

Excited state proton transfer kinetics of 4-hydroxydiphenyl ether

Rajendiran

Swaminathan

1997

Int. J. Chem. Kinet.

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Fluorimetric titrations of 4-hydroxydiphenyl ether and its anion give stretched sigmoid curves with two inflection points. This reveals that the rates of excited state proton exchange are comparable to the rates of deactivation of the conjugate pair. These curves are analyzed using the lifetimes of the species. The excited state equilibrium constants determined from rate constants and by other methods are compared.

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“…Such nonradiative excited state quenching by nonadiabatic geminate proton recombination has already been reported for 1-naphthol. 70,71 In order to obtain additional support for the involvement of the 5-and 6-OH protons of DHICA oligomers in the excited state relaxation process we measured steady state fluorescence spectra of a highly purified sample of the 4,4′-dimer in MeOH and in 0.1 M NaOH (pH 13) ( Figure SI4). In MeOH solution we observe a fluorescence band at ∼350 nm, reminiscent of that for monomeric DHICA in MeOH.…”

Section: ■ Discussionmentioning

confidence: 99%

Superior Photoprotective Motifs and Mechanisms in Eumelanins Uncovered

et al. 2014

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Human pigmentation is a complex phenomenon commonly believed to serve a photoprotective function through the generation and strategic localization of black insoluble eumelanin biopolymers in sun exposed areas of the body. Despite compelling biomedical relevance to skin cancer and melanoma, eumelanin photoprotection is still an enigma: What makes this pigment so efficient in dissipating the excess energy brought by harmful UV-light as heat? Why has Nature selected 5,6-dihydroxyindole-2-carboxylic acid (DHICA) as the major building block of the pigment instead of the decarboxylated derivative (DHI)? By using pico-and femtosecond fluorescence spectroscopy we demonstrate herein that the excited state deactivation in DHICA oligomers is 3 orders of magnitude faster compared to DHI oligomers. This drastic effect is attributed to their specific structural patterns enabling multiple pathways of intra-and interunit proton transfer. The discovery that DHICA-based scaffolds specifically confer uniquely robust photoprotective properties to natural eumelanins settles a fundamental gap in the biology of human pigmentation and opens the doorway to attractive advances and applications.

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Acid-base properties of 1-naphthol. Proton-induced fluorescence quenching

Cited by 108 publications

References 3 publications

Nuclear Magnetic Resonance Spectroscopy Investigations of Naphthalene-Based 1,2,3-Triazole Systems for Anion Sensing

Nuclear Magnetic Resonance Spectroscopy Investigations of Naphthalene-Based 1,2,3-Triazole Systems for Anion Sensing

Excited state proton transfer kinetics of 4-hydroxydiphenyl ether

Superior Photoprotective Motifs and Mechanisms in Eumelanins Uncovered

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