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D-π-A compounds with tunable intramolecular charge transfer achieved by incorporation of butenolide nitriles as acceptor moieties

AuthorsMoreno-Yruela, Carlos; Garín, Javier; Orduna, Jesús ; Franco, Santiago; Quintero, Estefanía; López Navarrete, Juan T.; Diosdado, Beatriz E.; Villacampa, Belén; Casado, Juan; Andreu, Raquel
Issue Date2015
PublisherAmerican Chemical Society
CitationJournal of Organic Chemistry 80(24): 12115-12128 (2015)
AbstractChromophores 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.
Publisher version (URL)https://doi.org/10.1021/acs.joc.5b02051
Identifiersdoi: 10.1021/acs.joc.5b02051
issn: 0022-3263
e-issn: 1520-6904
Appears in Collections:(ICMA) Artículos
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