Bromo-and chloro-derivatives of dibenzylideneacetone: Experimental and theoretical study of the first molecular hyperpolarizability and two-photon absorption

Santos, Francisco A.; Abegão, Luis M. G.; Fonseca, Ruben D.; Alcântara, Aline M.; Mendonça, Cleber Renato; Valle, Marcelo Siqueira; Alencar, Márcio A. R. C.; Kamada, Kei; Boni, Leonardo De; Rodrigues, José J.

doi:10.1016/j.jphotochem.2018.10.012

Cited by 18 publications

(11 citation statements)

References 44 publications

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“…From comparison with the theoretical and experimental results, a good agreement was observed for the dynamic first molecular hyperpolarizability, in particular when it is taken into account the experimental error (20%) in HRS measurement. In fact, the comparison between the measured βHRS values of the studied compounds with similar ones reported previously, such as chalcones derivatives [28], oxazoles dyes [29], and dibenzylideneacetones derivatives with different substituents [49], reveals the potential of using the current compounds as frequency converters. For example, the reported βHRS value of a compound from the same molecular structure family (1E,4E)-1,5-bis(4-bromophenyl)penta-1,4-dien-3-one was 25 × 10 −30 •cm 4 •statvolt −1 [49], which is, two times lower than the value obtained for the 4-DMDBA.…”

Section: First Molecular Hyperpolarizabilitysupporting

confidence: 74%

“…In fact, the comparison between the measured βHRS values of the studied compounds with similar ones reported previously, such as chalcones derivatives [28], oxazoles dyes [29], and dibenzylideneacetones derivatives with different substituents [49], reveals the potential of using the current compounds as frequency converters. For example, the reported βHRS value of a compound from the same molecular structure family (1E,4E)-1,5-bis(4-bromophenyl)penta-1,4-dien-3-one was 25 × 10 −30 •cm 4 •statvolt −1 [49], which is, two times lower than the value obtained for the 4-DMDBA. Another example, an oxazole derivative 4-((5-phenyloxazol-2-yl)ethynyl)benzonitrile [29], with a longer π-electron backbone length presented a value of 45 × 10 −30 •cm 4 •statvolt −1 , which still is lower than the 4-DMDBA.…”

Section: First Molecular Hyperpolarizabilitysupporting

confidence: 74%

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Nonlinear Optical Study in a Set of Dibenzylideneacetone Derivatives with Potential for Optical Frequency Conversion

et al. 2020

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The search for advanced optical materials, in particular, materials with nonlinear optical responses, has, in the last years, experienced substantial growth due to their vast applications in the photonics field. One of those applications is ultra-fast optical frequency conversion, in the optics communications field. Organic compounds have emerged as promising candidates for raw materials to develop nonlinear optical devices, such as optical converters, due to their intrinsic ultra-fast electronic responses. Also, the easy tailoring of organic molecular structures makes organic materials much more appealing than the inorganic ones. In this work, we have performed a linear and nonlinear optical characterization of a set of dibenzylideneacetone derivatives. The nonlinear optical responses investigated correspond to second- and third-order nonlinear processes, namely, first electronic molecular hyperpolarizability and two-photon absorption cross-section, respectively. The value of the first electronic molecular hyperpolarizability, up to 52 cm4·statvolt−1, could be considered a robust value when compared to the short-sized π-electron backbone length of the studied compounds. Such results suggest that these compounds exhibit the potential to be used as optical frequency converters. Quantum chemical calculations were used to predict the theoretical value of the first molecular hyperpolarizability, as well as to simulate the one- and two-photon absorption spectra for all compounds.

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Section: First Molecular Hyperpolarizabilitysupporting

confidence: 74%

Section: First Molecular Hyperpolarizabilitysupporting

confidence: 74%

Nonlinear Optical Study in a Set of Dibenzylideneacetone Derivatives with Potential for Optical Frequency Conversion

et al. 2020

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“…All compounds showed values for the rst molecular hyperpolarizability higher than the standard sample. As mentioned elsewhere, [43][44][45] centrosymmetrical molecular structures should have an extremely low second-order nonlinear optical signal. Consequently, it was expected that the compounds investigated in this work, which have a low centrosymmetric structure nature, present signicant HRS signal, such as the compound 16c which presented a value three times higher than the reference compound.…”

Section: Discussionmentioning

confidence: 79%

First molecular electronic hyperpolarizability of series of π-conjugated oxazole dyes in solution: an experimental and theoretical study

et al. 2019

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“…However, most of these investigations are purely computational and report predictions of these properties obtained by means of quantum simulations. , One of the few experimental works performed to measure two-photon absorption as well as second hyperpolarizability (γ) by four-wave mixing spectroscopy deals with only one investigated organic dye . Only more recently, several research works have reported both two-photon absorption and first hyperpolarizability (β) obtained either computationally , or by a joint computational and experimental effort , in a series of organic systems. It is noteworthy that in all of these studies, the molecular dye exhibiting the largest two-photon absorption of the series never matched the one exhibiting the largest hyperpolarizability.…”

Section: Introductionmentioning

confidence: 99%

Uncovering Structure–Property Relationships in Push–Pull Chromophores: A Promising Route to Large Hyperpolarizability and Two-Photon Absorption

et al. 2020

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In this investigation, we report the first hyperpolarizabilities and two-photon absorption cross sections of a large series of 12 push–pull cationic chromophores. All of these dyes show a dipolar acceptor+–π–donor structure, where the nature of the donor and acceptor units and π-bridge was synthetically tuned to allow insightful comparisons among the molecules. The hyperpolarizability was obtained through a solvatochromic method, by exploiting the rare negative solvatochromism exhibited by the investigated compounds. The two-photon absorption cross sections were determined through two-photon excited fluorescence measurements by means of a tunable nanosecond laser system for sample excitation. The nonlinear optical properties were discussed relatively to the photoinduced intramolecular charge transfer occurring in these donor–acceptor systems, investigated by femtosecond transient absorption experiments. We found a strong increase in hyperpolarizability upon increasing the molecular conjugation. Unexpectedly, the hyperpolarizability is almost unaffected by an increase in donor/acceptor strength and intramolecular charge transfer degree. Differently, the two-photon absorption cross sections of these dyes are enhanced by an increase in both molecular conjugation and intramolecular charge transfer efficiency. Several recent literature works have reported at the same time scattered information about the hyperpolarizability and two-photon absorption of small organic molecules. Our investigation is, to the best of our knowledge, the first attempt to uncover detailed structure–property relationships for these two nonlinear optical properties. Our results represent a promising route to achieve large hyperpolarizability and two-photon absorption in push–pull dyes and may drive the design of new efficient nonlinear optical materials.

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Bromo-and chloro-derivatives of dibenzylideneacetone: Experimental and theoretical study of the first molecular hyperpolarizability and two-photon absorption

Cited by 18 publications

References 44 publications

Nonlinear Optical Study in a Set of Dibenzylideneacetone Derivatives with Potential for Optical Frequency Conversion

Nonlinear Optical Study in a Set of Dibenzylideneacetone Derivatives with Potential for Optical Frequency Conversion

First molecular electronic hyperpolarizability of series of π-conjugated oxazole dyes in solution: an experimental and theoretical study

Uncovering Structure–Property Relationships in Push–Pull Chromophores: A Promising Route to Large Hyperpolarizability and Two-Photon Absorption

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