It is shown that 4-methyl-7-(4-hydroxyphenyl)-[1,2,4]-triazolo[3,2-c][1,2,4]triazole exhibits a rich photoinduced protolytic behavior: Förster cycle shows that the protonated nitrogen of the triazolo-triazole ring is a weak photoacid, with DeltapKa=-3; furthermore, at moderately basic pH its deprotonated monoanion exhibits a long distance water mediated phototautomerism, in which the hydroxyl group releases a proton to solvent and a basic nitrogen of the triazolo-triazole fused ring, different from that protonated in the neutral species, is protonated by the solvent.
Phototautomerism of triazolo-triazole scaffold / Capobianco, Amedeo; Di Donato, Mariangela; Caruso, Tonino; Centore, Roberto; Lapini, Andrea; Manfredi, Carla; Velardo, Amalia; Volino, Sabato; Peluso, Andrea. - In: JOURNAL OF MOLECULAR STRUCTURE. - ISSN 0022-2860. - 1203:(2020), p. 127368. [10.1016/j.molstruc.2019.127368]
Phototautomerism of triazolo-triazole scaffold
Roberto Centore
;Carla Manfredi;Sabato Volino;
2020
Abstract
It is shown that 4-methyl-7-(4-hydroxyphenyl)-[1,2,4]-triazolo[3,2-c][1,2,4]triazole exhibits a rich photoinduced protolytic behavior: Förster cycle shows that the protonated nitrogen of the triazolo-triazole ring is a weak photoacid, with DeltapKa=-3; furthermore, at moderately basic pH its deprotonated monoanion exhibits a long distance water mediated phototautomerism, in which the hydroxyl group releases a proton to solvent and a basic nitrogen of the triazolo-triazole fused ring, different from that protonated in the neutral species, is protonated by the solvent.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
