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

Carlos Moreno-Yruela; Javier Garín; Jesús Orduna; Santiago Franco; Estefanía Quintero; Juan T López Navarrete; Beatriz E Diosdado; Belén Villacampa; Juan Casado; Raquel Andreu

doi:10.1021/acs.joc.5b02051

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

Carlos Moreno-Yruela, Javier Garín, Jesús Orduna, Santiago Franco, Estefanía Quintero, Juan T López Navarrete, Beatriz E Diosdado, Belén Villacampa, Juan Casado, Raquel Andreu

30 Citations (Scopus)

Abstract

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.

Original language	English
Journal	Journal of Organic Chemistry
Volume	80
Issue number	24
Pages (from-to)	12115-28
Number of pages	14
ISSN	0022-3263
DOIs	https://doi.org/10.1021/acs.joc.5b02051
Publication status	Published - 20 Nov 2015

Keywords

Journal Article
Research Support, Non-U.S. Gov't

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Moreno-Yruela, C., Garín, J., Orduna, J., Franco, S., Quintero, E., López Navarrete, J. T., Diosdado, B. E., Villacampa, B., Casado, J., & Andreu, R. (2015). D-π-A Compounds with Tunable Intramolecular Charge Transfer Achieved by Incorporation of Butenolide Nitriles as Acceptor Moieties. Journal of Organic Chemistry, 80(24), 12115-28. https://doi.org/10.1021/acs.joc.5b02051

Moreno-Yruela, C, Garín, J, Orduna, J, Franco, S, Quintero, E, López Navarrete, JT, Diosdado, BE, Villacampa, B, Casado, J & Andreu, R 2015, 'D-π-A Compounds with Tunable Intramolecular Charge Transfer Achieved by Incorporation of Butenolide Nitriles as Acceptor Moieties', Journal of Organic Chemistry, vol. 80, no. 24, pp. 12115-28. https://doi.org/10.1021/acs.joc.5b02051

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abstract = "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.",

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doi = "10.1021/acs.joc.5b02051",

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T1 - D-π-A Compounds with Tunable Intramolecular Charge Transfer Achieved by Incorporation of Butenolide Nitriles as Acceptor Moieties

AU - Moreno-Yruela, Carlos

AU - Garín, Javier

AU - Orduna, Jesús

AU - Franco, Santiago

AU - Quintero, Estefanía

AU - López Navarrete, Juan T

AU - Diosdado, Beatriz E

AU - Villacampa, Belén

AU - Casado, Juan

AU - Andreu, Raquel

PY - 2015/11/20

Y1 - 2015/11/20

N2 - 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.

AB - 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.

KW - Journal Article

KW - Research Support, Non-U.S. Gov't

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DO - 10.1021/acs.joc.5b02051

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JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 24

ER -

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

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