Second harmonic generation in pyrazoline derivatives of dibenzylideneacetones and chalcone: A combined experimental and theoretical approach

Araújo, Raiane Sodré de; Alcântara, Aline M.; Abegão, Luis M. G.; Souza, Yago Pereira de; Brandão-Silva, Antônio C.; Machado, R.; Rodrigues, José J.; Pliego, Josefredo R.; D’Errico, Francesco; Valle, Marcelo Siqueira; Alencar, Márcio A. R. C.

doi:10.1016/j.jphotochem.2019.112147

Cited by 18 publications

(10 citation statements)

References 69 publications

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“…In the crystals 2PANC and 3PANC, two adjacent molecules are organized into inversion dimers via a pair of bifurcated hydrogen bonds from the oxygen acceptor (O1) with R 2 1 (7) and R 2 2 (8) graph-set motifs (Figure 3, Table S3). The dimeric clusters in 2PANC are extended into one-dimensional linear chains, propagating along the [111] direction by the weak intermolecular interactions C9−H9A S4a).…”

Section: Resultsmentioning

confidence: 99%

“…Chalcone derivatives are found to exhibit noteworthy nonlinear optical (NLO) properties accompanied by an ultrafast (picosecond–femtosecond) response. − Owing to this, chalcones have been widely studied for their possible uses in frequency conversion, two-photon absorption (2PA) spectroscopy, optoelectronics, optical power limiting (OPL), and all-optical switching (AOS) applications. − The electron donors and acceptors with π-conjugated molecular systems (D−π–A type) were often used to design molecules for larger values of first and second hyperpolarizabilities (β and γ). ,, These molecular systems of the materials depict strong charge transfer characteristics between electron donor and acceptor groups, which usually enhance the NLO properties. Therefore, it is important to know the structure–property relationships of newly prepared chalcones.…”

Section: Introductionmentioning

confidence: 99%

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Ultrafast Nonlinear Optical and Structure–Property Relationship Studies of Pyridine-Based Anthracene Chalcones Using Z-Scan, Degenerate Four-Wave Mixing, and Computational Approaches

Maidur¹,

Patil

Katturi

et al. 2021

J. Phys. Chem. B

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The structural, thermal, linear, and femtosecond third-order nonlinear optical (NLO) properties of two pyridine-based anthracene chalcones, (2E)-1-(anthracen-9-yl)-3-(pyridin-2-yl)prop-2-en-1-one (2PANC) and (2E)-1-(anthracen-9-yl)-3-(pyridin-3-yl)prop-2-en-1-one (3PANC), were investigated. These two chalcones were synthesized following the Claisen–Schmidt condensation method. Optically transparent single crystals were achieved using a slow evaporation solution growth technique. The presence of functional groups in these molecules was established by Fourier transform infrared and NMR spectroscopic data. The detailed solid-state structure of both chalcones was determined from the single-crystal X-ray diffraction data. Both crystals crystallized in the centrosymmetric triclinic space group P1̅ with the nuance of unit cell parameters. The crystals (labeled as 2PANC and 3PANC) have been found to be transparent optically [in the entire visible spectral region] and were found to be thermally stable up to 169 and 194 °C, respectively. The intermolecular interactions were investigated using the Hirshfeld surface analysis, and the band structures (highest occupied molecular orbital–lowest unoccupied molecular orbital, excited-state energies, global chemical reactivity descriptors, and molecular electrostatic potentials) were studied using density functional theory (DFT) techniques. The ultrafast third-order NLO properties were investigated using (a) Z-scan and (b) degenerate four-wave mixing (DFWM) techniques using ∼50 fs pulses at 800 nm (1 kHz, ∼4 mJ) from a Ti:sapphire laser amplifier. Two-photon-assisted reverse saturable absorption, self-focusing nonlinear refraction, optical limiting, and optical switching behaviors were witnessed from the Z-scan data. 3PANC demonstrated a stronger two-photon absorption coefficient, while 2PANC depicted a stronger nonlinear refractive index among the two. The time-resolved DFWM data demonstrated that the decay times of 2PANC and 3PANC were ∼162 and ∼180 fs, respectively. The second hyperpolarizability (γ) values determined by DFT, Z-scan, and DFWM were found to be in good correlation (with a magnitude of ∼10–34 esu). The ultrafast third-order NLO response, significant NLO properties, and thermal stability of these chalcones brands them as potential candidates for optical power limiting and switching applications.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Ultrafast Nonlinear Optical and Structure–Property Relationship Studies of Pyridine-Based Anthracene Chalcones Using Z-Scan, Degenerate Four-Wave Mixing, and Computational Approaches

Maidur¹,

Patil

Katturi

et al. 2021

J. Phys. Chem. B

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“…The simple chalcone was synthesized from acetophenone and benzaldehyde using NaOH as a catalyst. DBA or DBA‐OCH 3 or chalcones was then treated with phenylhydrazine followed by subsequent addition of H 2 SO 4 and was allowed to stir for 5 h giving the required product with 52 % and 95 % yield, respectively [75] . (Scheme 18)…”

Section: Chemistry Of Chalcone Derived Pyrazoline Derivativesmentioning

confidence: 99%

“…The synthesized compounds were experimentally and theoretically proven to have good potential for application in electronic devices based on second‐order nonlinear responses [75] …”

Section: Chemistry Of Chalcone Derived Pyrazoline Derivativesmentioning

confidence: 99%

An Overview on Synthesis and Biological Activity of Chalcone Derived Pyrazolines

2021

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Chalcones are α, β unsaturated aromatic ketones having enone moiety and exhibit a wide array of pharmaceutical and biological activities. Chalcones possess a wide range of biological activities such as anticancer, antituberculosis, antidiabetic, antioxidant, anti‐inflammatory, antimicrobial, and antimalarial. Nitrogen‐containing heterocyclic compounds are an extremely important class of organic compounds with a broad spectrum of pharmaceutical activities. Pyrazolines are N‐ heterocyclic compounds that exhibit a wide range of pharmaceutical activities and are synthesized from chalcone with enhanced biological activity. The present study summarizes the chemistry of various chalcone‐based pyrazolines and their derivatives with the available data till 2021.

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“…Chalcones, also known as α, β-unsaturated ketones, are present in an extensive range of optical applications, such as second harmonic generation [ 8 , 9 , 10 , 11 , 12 , 13 ], holographic recording technology [ 14 ], and photorefractive polymers [ 15 ], to name a few. In addition, owing to the intrinsic structural flexibility, functionality, and electron mobility of chalcones, modulation of third-order nonlinearities has been explored [ 1 , 2 , 4 , 16 , 17 ].…”

Section: Introductionmentioning

confidence: 99%

Two-Photon Absorption and Multiphoton Excited Fluorescence of Acetamide-Chalcone Derivatives: The Role of Dimethylamine Group on the Nonlinear Optical and Photophysical Properties

et al. 2023

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This work studied the effect of different electron-withdrawing and electron-donating groups on the linear and nonlinear optical properties of acetamide-chalcone derivatives. The results showed that the addition of the dimethylamine group led to a large fluorescence emission (71% of fluorescence quantum yield in DMSO solution) that can be triggered by two and three-photon excitations, which is essential for biological applications. Furthermore, dimethylamine also red-shifts the lower energy state by approximately 90 nm, increasing the two-photon absorption cross-section of the lower energy band by more than 100% compared with the other studied compounds. All compounds presented two-electronic states observed through one and two-photon absorption spectroscopy and confirmed by Quantum Chemistry Calculations (QCCs). QCC results were also used to model the experimental two-photon absorption cross-sectional spectrum by the Sum-Over-States (SOS) approach, revealing a dependence between the coupling of the ground state with the first excited state and the transition dipole moment between these states.

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Second harmonic generation in pyrazoline derivatives of dibenzylideneacetones and chalcone: A combined experimental and theoretical approach

Cited by 18 publications

References 69 publications

Ultrafast Nonlinear Optical and Structure–Property Relationship Studies of Pyridine-Based Anthracene Chalcones Using Z-Scan, Degenerate Four-Wave Mixing, and Computational Approaches

Ultrafast Nonlinear Optical and Structure–Property Relationship Studies of Pyridine-Based Anthracene Chalcones Using Z-Scan, Degenerate Four-Wave Mixing, and Computational Approaches

An Overview on Synthesis and Biological Activity of Chalcone Derived Pyrazolines

Two-Photon Absorption and Multiphoton Excited Fluorescence of Acetamide-Chalcone Derivatives: The Role of Dimethylamine Group on the Nonlinear Optical and Photophysical Properties

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