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Solvent and pH-sensitive Fluorescence Response of Alloxazine
Journal of Photochemistry and Photobiology A: Chemistry ( IF 4.3 ) Pub Date : 2020-09-06 , DOI: 10.1016/j.jphotochem.2020.112888
Madhushree Mal , Debabrata Mandal

The fluorescence response of Alloxazine was found to be sensitive to solvent properties like polarity and H-bonding capacity, which also played a significant role in controlling the incidence of Alloxazine – Isoalloxazine photo-tautomerization. The latter was strongly promoted in polar, protic solvents like alcohols, via an N(1)→N(10) excited state proton transfer mechanism involving Alloxazine : solvent (1:2) intermolecular H-bonded complexes, similar to that proposed earlier for 7,8-Dimethylalloxazine. Even for Alloxazine in aqueous solutions over a wide range of acid/base strengths from pH = 2 to pH = 13, the fluorescence was found to be always dominated by two emissive species, which were identified as the Alloxazine – Isoalloxazine couple, irrespective of the pH of the solution, and of the nature of the ionic equilibrium prevailing at that pH. The results in aqueous pH solutions could be explained by a mechanism where the photo-tautomerization was resolved into two independent dynamics involving deprotonation and protonation of the N(1) and N(10) atoms of Alloxazine, respectively.



中文翻译:

阿洛嗪的溶剂和pH敏感荧光响应

发现Alloxazine的荧光响应对溶剂性质(如极性和H键容量)敏感,这在控制Alloxazine – Isoalloxazine光互变异构的发生率中也起着重要作用。后者在极性质子溶剂(如醇)中通过N(1)→N(10)激发态质子转移机制(包括脲嘧啶:溶剂(1:2)分子间氢键结合的络合物)而得到了强烈促进,类似于先前提出的7,8-二甲基别恶嗪。即使在水溶液的酸/碱强度范围从pH = 2到pH = 13的水溶液中,Alloxazine的荧光也始终由两个发射物种占主导,这两个发光物种被确定为Alloxazine – Isoalloxazine对,无论溶液的pH值,以及该pH值下离子平衡的性质。

更新日期:2020-09-18
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