D−π–A Compounds with Tunable Intramolecular Charge Transfer Achieved by Incorporation of Butenolide Nitriles as Acceptor Moieties

D−π–A Compounds with Tunable Intramolecular Charge Transfer Achieved by Incorporation of Butenolide Nitriles as Acceptor Moieties

Chromophores where a polyenic spacer separates a 4H-pyranylidene or benzothiazolylidene donor and three different butenolide nitriles have been synthesized and characterized. The role of 2­(5H)-furanones as acceptor units on the polarization and the second-order nonlinear (NLO) properties has been s...

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Veröffentlicht in:Journal of organic chemistry 2015-12, Vol.80 (24), p.12115-12128
Hauptverfasser: Moreno-Yruela, Carlos, Garín, Javier, Orduna, Jesús, Franco, Santiago, Quintero, Estefanía, López Navarrete, Juan T, Diosdado, Beatriz E, Villacampa, Belén, Casado, Juan, Andreu, Raquel
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container_end_page 12128
container_issue 24
container_start_page 12115
container_title Journal of organic chemistry
container_volume 80
creator Moreno-Yruela, Carlos
Garín, Javier
Orduna, Jesús
Franco, Santiago
Quintero, Estefanía
López Navarrete, Juan T
Diosdado, Beatriz E
Villacampa, Belén
Casado, Juan
Andreu, Raquel
description Chromophores where a polyenic spacer separates a 4H-pyranylidene or benzothiazolylidene donor and three different butenolide nitriles have been synthesized and characterized. The role of 2­(5H)-furanones as acceptor units on the polarization and the second-order nonlinear (NLO) properties has been studied. Thus, their incorporation gives rise to moderately polarized structures with NLO responses that compare favorably to those of related compounds featuring more efficient electron-withdrawing moieties. Derivatives of the proaromatic butenolide PhFu show the best nonlinearities. Benzothiazolylidene-containing chromophores present less alternated structures than their pyranylidene analogues, and, unlike most merocyanines, the degree of charge transfer does not decrease on lengthening the π-bridge.
doi_str_mv 10.1021/acs.joc.5b02051
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title D−π–A Compounds with Tunable Intramolecular Charge Transfer Achieved by Incorporation of Butenolide Nitriles as Acceptor Moieties
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