The Cyclic Hydrogen-Bonded 6-Azaindole Trimer and its Prominent Excited-State Triple-Proton-Transfer Reaction.
Angew Chem Int Ed Engl
; 57(18): 5020-5024, 2018 04 23.
Article
em En
| MEDLINE
| ID: mdl-29468788
ABSTRACT
The compound 6-azaindole undergoes self-assembly by formation of N(1)-Hâ
â
â
N(6) hydrogen bonds (H bonds), forming a cyclic, triply H-bonded trimer. The formation phenomenon is visualized by scanning tunneling microscopy. Remarkably, the H-bonded trimer undergoes excited-state triple proton transfer (ESTPT), resulting in a proton-transfer tautomer emission maximized at 435â
nm (325â
nm of the normal emission) in cyclohexane. Computational approaches affirm the thermodynamically favorable H-bonded trimer formation and the associated ESTPT reaction. Thus, nearly half a century after Michael Kasha discovered the double H-bonded dimer of 7-azaindole and its associated excited-state double-proton-transfer reaction, the triply H-bonded trimer formation of 6-azaindole and its ESTPT reaction are demonstrated.
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Coleções:
01-internacional
Base de dados:
MEDLINE
Idioma:
En
Ano de publicação:
2018
Tipo de documento:
Article