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Synthesis of Bright Alkenyl‐1 H ‐1,2,4‐triazoles: A Theoretical and Photophysical Study
Author(s) -
Cebrián Cristina,
de Mata Muñoz Juan,
Strassert Cristian Alejandro,
Prieto Pilar,
DíazOrtiz Ángel,
De Cola Luisa,
de la Hoz Antonio
Publication year - 2014
Publication title -
chempluschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.801
H-Index - 61
ISSN - 2192-6506
DOI - 10.1002/cplu.201402153
Subject(s) - reactivity (psychology) , chemistry , excited state , silylation , density functional theory , solvent , sodium hydroxide , photochemistry , computational chemistry , combinatorial chemistry , organic chemistry , catalysis , medicine , physics , alternative medicine , pathology , nuclear physics
A sustainable synthesis of alkenyl‐1 H ‐1,2,4‐triazoles through the Hiyama reaction is reported, which employs water as solvent and sodium hydroxide to activate the silyl group under microwave irradiation, thereby leading to high product yields (51–93 %) in very short reaction times. Two substitution patterns were attained owing to the different reactivity of the third and fifth positions of the 1 H ‐1,2,4‐triazole unit, as evidenced by calculated condensed Fukui functions. Moreover, all compounds are good blue emitters ( Φ F up to 0.69) in THF solution, although they exhibit an optical behavior dependent on the substitution. Excited‐state theoretical investigations by the configuration interaction singles method and time‐dependent density functional theory were performed not only to support and elucidate the studied photophysical properties, but also to create a predictive model to reduce the cost and optimize the search for new blue emitters based on this class of alkenyl‐1 H ‐1,2,4‐triazoles.