Synthesis of Bright Alkenyl-1H-1,2,4-triazoles: A Theoretical and Photophysical Study

Cebrián, C.; Mata Muñoz, J.; Strassert, C. A.; Prieto, P.; Díaz-Ortiz, Á.; De Cola, L.; Hoz, A.

Abstract

Abstract A sustainable synthesis of alkenyl-1H-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 1H-1,2,4-triazole unit, as evidenced by calculated condensed Fukui functions. Moreover, all compounds are good blue emitters (ΦF 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-1H-1,2,4-triazoles.