Enhanced intramolecular charge transfer in new type donor-acceptor substituted perylenes

Aleksey A. Vasilev, Chen Li, Klaus Müllen, Kurt De Mey, I. Asselberghs, K. Clays, B. Champagne, S.E. Angelova, M.I. Spassova

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Here we report the facile synthesis and physical characterization of new type N-(2,6-diisopropylphenyl)-3,4-perylenedicarboximides (PMI) with alkyl-substituted quinoline-4(1H)-ylidenemethyl or acridine-9(10H)-ylidenemethyl units as strong donors in the 9-position. When compared to parent PMI, these perylene dyes, 9-((1-methylquinoline-4(1H)-ylidene)methyl)-PMI, 9-((1-benzylquinoline-4(1H)ylidene)methyl)-PMI, 9-((1-heptylquinoline-4(1H)- ylidene)methyl)-PMI, and 9-((10-methylacridine-9(10H)-ylidene)methyl)-PMI, show a pronounced bathochromic shift of their electronic absorption with solvatochromism because of their intramolecular charge transfer. The solvatochromic behavior of these dyes is further confirmed by second-order nonlinear optical experiments. Remarkably high second-order nonlinear optical values (β up to 1300 ± 50 × 10 esu at 880 nm in dichloromethane) are obtained by femtosecond hyper-Rayleigh scattering. The one-step synthesis together with the spectroscopic, solvatochromic, and nonlinear optical characteristics qualify these new types of perylene dyes as promising candidates for solvent polarity probes, photovoltaics, or nonlinear optical applications.
langue originaleAnglais
Pages (de - à)22711-22719
Nombre de pages9
journalJournal of physical chemistry. C
Volume116
Numéro de publication43
Les DOIs
étatPublié - 1 nov. 2012

Empreinte digitale

Perylene
Charge transfer
Coloring Agents
Dyes
dyes
charge transfer
Acridines
Rayleigh scattering
Methylene Chloride
quinoline
Dichloromethane
synthesis
polarity
probes
shift
electronics
Experiments

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Vasilev, A. A., Li, C., Müllen, K., De Mey, K., Asselberghs, I., Clays, K., ... Spassova, M. I. (2012). Enhanced intramolecular charge transfer in new type donor-acceptor substituted perylenes. Journal of physical chemistry. C, 116(43), 22711-22719. https://doi.org/10.1021/jp306848f
Vasilev, Aleksey A. ; Li, Chen ; Müllen, Klaus ; De Mey, Kurt ; Asselberghs, I. ; Clays, K. ; Champagne, B. ; Angelova, S.E. ; Spassova, M.I. / Enhanced intramolecular charge transfer in new type donor-acceptor substituted perylenes. Dans: Journal of physical chemistry. C. 2012 ; Vol 116, Numéro 43. p. 22711-22719.
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abstract = "Here we report the facile synthesis and physical characterization of new type N-(2,6-diisopropylphenyl)-3,4-perylenedicarboximides (PMI) with alkyl-substituted quinoline-4(1H)-ylidenemethyl or acridine-9(10H)-ylidenemethyl units as strong donors in the 9-position. When compared to parent PMI, these perylene dyes, 9-((1-methylquinoline-4(1H)-ylidene)methyl)-PMI, 9-((1-benzylquinoline-4(1H)ylidene)methyl)-PMI, 9-((1-heptylquinoline-4(1H)- ylidene)methyl)-PMI, and 9-((10-methylacridine-9(10H)-ylidene)methyl)-PMI, show a pronounced bathochromic shift of their electronic absorption with solvatochromism because of their intramolecular charge transfer. The solvatochromic behavior of these dyes is further confirmed by second-order nonlinear optical experiments. Remarkably high second-order nonlinear optical values (β up to 1300 ± 50 × 10 esu at 880 nm in dichloromethane) are obtained by femtosecond hyper-Rayleigh scattering. The one-step synthesis together with the spectroscopic, solvatochromic, and nonlinear optical characteristics qualify these new types of perylene dyes as promising candidates for solvent polarity probes, photovoltaics, or nonlinear optical applications.",
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Vasilev, AA, Li, C, Müllen, K, De Mey, K, Asselberghs, I, Clays, K, Champagne, B, Angelova, SE & Spassova, MI 2012, 'Enhanced intramolecular charge transfer in new type donor-acceptor substituted perylenes', Journal of physical chemistry. C, VOL. 116, Numéro 43, p. 22711-22719. https://doi.org/10.1021/jp306848f

Enhanced intramolecular charge transfer in new type donor-acceptor substituted perylenes. / Vasilev, Aleksey A.; Li, Chen; Müllen, Klaus; De Mey, Kurt; Asselberghs, I.; Clays, K.; Champagne, B.; Angelova, S.E.; Spassova, M.I.

Dans: Journal of physical chemistry. C, Vol 116, Numéro 43, 01.11.2012, p. 22711-22719.

Résultats de recherche: Contribution à un journal/une revueArticle

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T1 - Enhanced intramolecular charge transfer in new type donor-acceptor substituted perylenes

AU - Vasilev, Aleksey A.

AU - Li, Chen

AU - Müllen, Klaus

AU - De Mey, Kurt

AU - Asselberghs, I.

AU - Clays, K.

AU - Champagne, B.

AU - Angelova, S.E.

AU - Spassova, M.I.

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N2 - Here we report the facile synthesis and physical characterization of new type N-(2,6-diisopropylphenyl)-3,4-perylenedicarboximides (PMI) with alkyl-substituted quinoline-4(1H)-ylidenemethyl or acridine-9(10H)-ylidenemethyl units as strong donors in the 9-position. When compared to parent PMI, these perylene dyes, 9-((1-methylquinoline-4(1H)-ylidene)methyl)-PMI, 9-((1-benzylquinoline-4(1H)ylidene)methyl)-PMI, 9-((1-heptylquinoline-4(1H)- ylidene)methyl)-PMI, and 9-((10-methylacridine-9(10H)-ylidene)methyl)-PMI, show a pronounced bathochromic shift of their electronic absorption with solvatochromism because of their intramolecular charge transfer. The solvatochromic behavior of these dyes is further confirmed by second-order nonlinear optical experiments. Remarkably high second-order nonlinear optical values (β up to 1300 ± 50 × 10 esu at 880 nm in dichloromethane) are obtained by femtosecond hyper-Rayleigh scattering. The one-step synthesis together with the spectroscopic, solvatochromic, and nonlinear optical characteristics qualify these new types of perylene dyes as promising candidates for solvent polarity probes, photovoltaics, or nonlinear optical applications.

AB - Here we report the facile synthesis and physical characterization of new type N-(2,6-diisopropylphenyl)-3,4-perylenedicarboximides (PMI) with alkyl-substituted quinoline-4(1H)-ylidenemethyl or acridine-9(10H)-ylidenemethyl units as strong donors in the 9-position. When compared to parent PMI, these perylene dyes, 9-((1-methylquinoline-4(1H)-ylidene)methyl)-PMI, 9-((1-benzylquinoline-4(1H)ylidene)methyl)-PMI, 9-((1-heptylquinoline-4(1H)- ylidene)methyl)-PMI, and 9-((10-methylacridine-9(10H)-ylidene)methyl)-PMI, show a pronounced bathochromic shift of their electronic absorption with solvatochromism because of their intramolecular charge transfer. The solvatochromic behavior of these dyes is further confirmed by second-order nonlinear optical experiments. Remarkably high second-order nonlinear optical values (β up to 1300 ± 50 × 10 esu at 880 nm in dichloromethane) are obtained by femtosecond hyper-Rayleigh scattering. The one-step synthesis together with the spectroscopic, solvatochromic, and nonlinear optical characteristics qualify these new types of perylene dyes as promising candidates for solvent polarity probes, photovoltaics, or nonlinear optical applications.

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Vasilev AA, Li C, Müllen K, De Mey K, Asselberghs I, Clays K et al. Enhanced intramolecular charge transfer in new type donor-acceptor substituted perylenes. Journal of physical chemistry. C. 2012 nov. 1;116(43):22711-22719. https://doi.org/10.1021/jp306848f