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• W2049303205 abstract "Lumichrome photophysical properties at different pH were characterized by UV–vis spectroscopy and steady-state and time-resolved fluorescence techniques, in four forms of protonation/deprotonation: neutral form, two monoanions, and dianion. The excited-state lifetimes of these forms of lumichrome were measured and discussed. The results were compared to those obtained for similar forms of alloxazine and/or isoalloxazine, and also to those of 1-methyl- and 3-methyllumichrome and 1,3-dimethyllumichrome. The absorption, emission, and synchronous spectra of lumichrome, 1-methyl- and 3-methyllumichrome, and 1,3-dimethyllumichrome at different pH were measured and used in discussion of fluorescence of neutral and deprotonated forms of lumichrome. The analysis of steady-state and time-resolved spectra and the DFT calculations both predict that the N(1) monoanion and the N(1,3) dianion of lumichrome have predominantly isoalloxazinic structures. Additionally, we confirmed that neutral lumichrome exists in its alloxazinic form only, in both the ground and the excited state. We also confirmed the existence and the alloxazinic structure of a second N(3) monoanion. The estimated values of pKa = 8.2 are for the equilibrium between neutral lumichrome and alloxazinic and isoalloxazinic monoanions, with proton dissociation from N(1)–H and N(3)–H groups proceeding at the almost the same pH, while the second value pKa = 11.4 refers to the formation of the isoalloxazinic dianion in the ground state." @default.
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• W2049303205 date "2012-07-10" @default.
• W2049303205 modified "2023-10-01" @default.
• W2049303205 title "Acid–Base Equilibriums of Lumichrome and its 1-Methyl, 3-Methyl, and 1,3-Dimethyl Derivatives" @default.
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• W2049303205 doi "https://doi.org/10.1021/jp300522h" @default.
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