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 Citationer (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.

Originalsprog	Engelsk
Tidsskrift	Journal of Organic Chemistry
Vol/bind	80
Udgave nummer	24
Sider (fra-til)	12115-28
Antal sider	14
ISSN	0022-3263
DOI	https://doi.org/10.1021/acs.joc.5b02051
Status	Udgivet - 20 nov. 2015

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10.1021/acs.joc.5b02051

Citationsformater

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, bind 80, nr. 24, s. 12115-28. https://doi.org/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",

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

U2 - 10.1021/acs.joc.5b02051

DO - 10.1021/acs.joc.5b02051

M3 - Journal article

C2 - 26588012

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VL - 80

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EP - 12128

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

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ER -

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

Abstract

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