Synthesis, characterization and nonlinear optical properties of symmetrically substituted dibenzylideneacetone derivatives

Reddy, N. Sunil Kumar; Badam, Rajashekar; Sattibabu, Romala; Molli, Muralikrishna; Muthukumar, V. Sai; Sai, S. Siva Sankara; Rao, G. Nageswara

doi:10.1016/j.cplett.2014.10.043

Cited by 33 publications

(5 citation statements)

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“…In such applications, organic NLO materials are more promising than inorganic materials (Boyd, 2003;Bosshard et al, 2001). Among the studied organic NLO materials, chalcone derivatives are attractive for their future use in NLO device functions like frequency conversion and optical limiting (Sunil Kumar Reddy et al, 2014;; Ramkumar et al, 2013; D'silva et al, 2012a; Kiran et al, 2010). The presence of a carbonyl group, a ISSN 1600-5767 # 2018 International Union of Crystallography long conjugated chain and various donor/acceptor substituents to two aromatic rings makes chalcone derivatives potential materials for NLO applications.…”

Section: Introductionmentioning

confidence: 99%

“…The C O group was always the acceptor. In this way, a number of acentric chalcone crystals exhibiting high nonlinear optical susceptibilities and transparent in the blue spectral region have been synthesized (Sunil Kumar Reddy et al, 2014;Ramkumar et al, 2013Ramkumar et al, , 2015D'silva et al, 2012a,b;Kiran et al, 2010;Goto et al, 1990;Zhao et al, 2000;Shkir et al, 2015;Gu et al, 2009;Gu, Ji, Patil, Dharmaprakash & Wang, 2008).…”

Section: Introductionmentioning

confidence: 99%

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Crystal growth and characterization of second- and third-order nonlinear optical chalcone derivative: (2E)-3-(5-bromo-2-thienyl)-1-(4-nitrophenyl)prop-2-en-1-one

et al. 2018

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Crystal growth and characterization of second-and third-order nonlinear optical chalcone derivative: (2E)-3-(5-bromo-2-thienyl)-1-(4-nitrophenyl)prop-2-en-1-one Experimental and computational studies of linear and nonlinear optical (NLO) properties of (2E)-3-(5-bromo-2-thienyl)-1-(4-nitrophenyl)prop-2-en-1-one (5B2SNC) single crystals are reported. Good-quality and large-sized single crystals of 5B2SNC were successfully grown and characterized by powder X-ray diffraction and high-resolution X-ray diffractometry techniques. 5B2SNC was found to crystallize in the monoclinic noncentrosymmetric space group Cc and possesses moderately good crystalline perfection. The linear optical properties were investigated using the absorption spectrum, which reveals a direct optical band gap of 3.1 eV. The thermal stability was studied with thermogravimetric analysis/differential thermal analysis. The powder second harmonic generation efficiency was evaluated by the Kurtz and Perry method, and 5B2SNC was found to be 26 times more efficient than urea standard. Third-order NLO properties were studied by the z-scan technique with a femtosecond laser. The second hyperpolarizability was obtained to be $1.45 Â 10 À31 e.s.u. The molecule reveals a strong reverse saturation absorption and negative nonlinear refraction. The molecule exhibited good optical limiting properties, and its limiting threshold was measured to be $3.2 mJ cm À2 . In addition, static electric dipole moments, linear polarizabilities, and first-and second-order hyperpolarizabilities were calculated by density functional theory (DFT). Highest occupied molecular orbital/lowest unoccupied molecular orbital band gaps were also evaluated by DFT calculations. The experimental and theoretical results showed that 5B2SNC exhibits excellent second-and third-order nonlinear optical properties.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Crystal growth and characterization of second- and third-order nonlinear optical chalcone derivative: (2E)-3-(5-bromo-2-thienyl)-1-(4-nitrophenyl)prop-2-en-1-one

et al. 2018

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“…Preparation of (1E,4E)-1,5-dip-tolylpenta-1,4-dien-3-one (3). 56 4-Methylbenzaldehyde 1 (4 ml, 33.8 mmol) and acetone 2 (1.27 ml, 17.2 mmol) were combined with ethanol (10 ml) and stirred for 15 min at room temperature. A solution of 10% aq.…”

Section: Discussionmentioning

confidence: 99%

Highly enantioselective asymmetric Henry reaction catalyzed by novel chiral phase transfer catalysts derived from cinchona alkaloids

2016

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A new type of di-site chiral phase transfer catalyst has been designed and synthesized from cinchona alkaloids as a chiral precursor. The prepared catalysts are applied in the asymmetric Henry reaction to a wide range of aldehydes using mild concentrations of a base and solvent and under room-temperature conditions. Under the optimized reaction conditions, the highest chemical yields up to 99% along with an excellent enantiomeric excess (ee) up to 99% were obtained using the prepared cinchona alkaloid based chiral phase transfer catalysts.

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“…Previous works, both experimental and theoretical, have shown that dibenzylideneacetone derivatives have second-and third-order nonlinear optical properties of promising magnitude for photonic applications, such as optical frequency converters, optical switching, and optical limiting [19][20][21][22][23]. These compounds stand out for their high synthetic versatility, which allows new structures to be obtained and can serve as channels for the optimization of nonlinear optical properties.…”

Section: Introductionmentioning

confidence: 99%

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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Synthesis, characterization and nonlinear optical properties of symmetrically substituted dibenzylideneacetone derivatives

Cited by 33 publications

References 42 publications

Crystal growth and characterization of second- and third-order nonlinear optical chalcone derivative: (2E)-3-(5-bromo-2-thienyl)-1-(4-nitrophenyl)prop-2-en-1-one

Crystal growth and characterization of second- and third-order nonlinear optical chalcone derivative: (2E)-3-(5-bromo-2-thienyl)-1-(4-nitrophenyl)prop-2-en-1-one

Highly enantioselective asymmetric Henry reaction catalyzed by novel chiral phase transfer catalysts derived from cinchona alkaloids

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

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