A New Isostructural Halogenated Chalcone with Optical Properties

Overview

Journal J Mol Model

Publisher Springer

Specialty Molecular Biology

Date 2021 Jan 27

PMID 33502611

Citations 2

Authors

Gabriela S Ludovico

Itallo H S Barros

Loide O Sallum

Rosa S Lima

Clodoaldo Valverde

Ademir J Camargo

Basilio Baseia

Hamilton B Napolitano

Affiliations

Soon will be listed here.

Abstract

Chalcones are organic compounds that present a number of properties. This study presents a comprehensive structural description of a new derivative of a chlorine-substituted chalcone in comparison with a bromine chalcone. Also, supermolecule and sum-over-state approach were used to describe the optical properties of these structures regarding the substitution of the bromine by the chlorine atom. In addition, the electrical properties, dipole moment, linear polarizability, and second IDRI hyperpolarizability were calculated. The linear refractive index and the third-order nonlinear macroscopic susceptibility were evaluated as a function of the applied electric field frequency. Furthermore, the quantum mechanics calculations that were implemented at the M06-2X/6-311++G(d,p) level of the theory for these isostructural chalcones indicate that the change in halogen atoms does not cause meaningful changes in their conformation. Finally, we can postulate that side-to-side and the antiparallel interactions are the interaction forces that drive the crystal growth for new isostructural chalcones. The NLO properties showed title compounds that are good candidates for use as NLO materials.

Citing Articles

Synthesis and Anti-gastric Cancer Activity by Targeting FGFR1 Pathway of Novel Asymmetric Bis-chalcone Compounds.

Nian C, Gan X, Liu Q, Wu Y, Kong M, Zhang P Curr Med Chem. 2024; 31(39):6521-6541.

PMID: 38847254 DOI: 10.2174/0109298673298420240530093525.

Remarkable Nonlinear Properties of a Novel Quinolidone Derivative: Joint Synthesis and Molecular Modeling.

Valverde C, Vinhal R, Naves L, Custodio J, Baseia B, Oliveira H Molecules. 2022; 27(8).

PMID: 35458577 PMC: 9028933. DOI: 10.3390/molecules27082379.

References

Won S, Liu C, Tsao L, Weng J, Ko H, Wang J . Synthetic chalcones as potential anti-inflammatory and cancer chemopreventive agents. Eur J Med Chem. 2005; 40(1):103-12. DOI: 10.1016/j.ejmech.2004.09.006. View

Nowakowska Z . A review of anti-infective and anti-inflammatory chalcones. Eur J Med Chem. 2006; 42(2):125-37. DOI: 10.1016/j.ejmech.2006.09.019. View

Salvi R, Cerqueira-Coutinho C, Ricci-Junior E, Santos S, Pinto S, Bernardes E . Diagnosing lung cancer using etoposide microparticles labeled with Tc. Artif Cells Nanomed Biotechnol. 2017; 46(2):341-345. DOI: 10.1080/21691401.2017.1307848. View

Luo M, Liang F, Song Y, Zhao D, Xu F, Ye N . MBOF (M = Ca, Sr): Two Noncentrosymmetric Alkaline Earth Fluorooxoborates as Promising Next-Generation Deep-Ultraviolet Nonlinear Optical Materials. J Am Chem Soc. 2018; 140(11):3884-3887. DOI: 10.1021/jacs.8b01263. View

Shi G, Wang Y, Zhang F, Zhang B, Yang Z, Hou X . Finding the Next Deep-Ultraviolet Nonlinear Optical Material: NHBOF. J Am Chem Soc. 2017; 139(31):10645-10648. DOI: 10.1021/jacs.7b05943. View

Martin A, Britton J, Easun T, Blake A, Lewis W, Schroder M . Hirshfeld Surface Investigation of Structure-Directing Interactions within Dipicolinic Acid Derivatives. Cryst Growth Des. 2015; 15(4):1697-1706. PMC: 4386464. DOI: 10.1021/cg5016934. View

Grabowski S . What is the covalency of hydrogen bonding?. Chem Rev. 2011; 111(4):2597-625. DOI: 10.1021/cr800346f. View

Lu T, Chen F . Multiwfn: a multifunctional wavefunction analyzer. J Comput Chem. 2011; 33(5):580-92. DOI: 10.1002/jcc.22885. View

Custodio J, Ternavisk R, Ferreira C, Figueredo A, Aquino G, Napolitano H . Using the Supermolecule Approach To Predict the Nonlinear Optics Potential of a Novel Asymmetric Azine. J Phys Chem A. 2018; 123(1):153-162. DOI: 10.1021/acs.jpca.8b07872. View

10.

Fonseca T, Sabino J, Castro M, Georg H . A theoretical investigation of electric properties of L-arginine phosphate monohydrate including environment polarization effects. J Chem Phys. 2010; 133(14):144103. DOI: 10.1063/1.3501237. View

11.

Santos O, Fonseca T, Sabino J, Georg H, Castro M . Polarization effects on the electric properties of urea and thiourea molecules in solid phase. J Chem Phys. 2015; 143(23):234503. DOI: 10.1063/1.4937481. View

12.

Kongsted J, Osted A, Mikkelsen K, Christiansen O . Second harmonic generation second hyperpolarizability of water calculated using the combined coupled cluster dielectric continuum or different molecular mechanics methods. J Chem Phys. 2004; 120(8):3787-98. DOI: 10.1063/1.1642593. View

13.

Perez-Moreno J, Clays K, Kuzyk M . A new dipole-free sum-over-states expression for the second hyperpolarizability. J Chem Phys. 2008; 128(8):084109. DOI: 10.1063/1.2834198. View

14.

Castet F, Rodriguez V, Pozzo J, Ducasse L, Plaquet A, Champagne B . Design and characterization of molecular nonlinear optical switches. Acc Chem Res. 2013; 46(11):2656-65. DOI: 10.1021/ar4000955. View

15.

Coe J, Paterson M . Approaching exact hyperpolarizabilities via sum-over-states Monte Carlo configuration interaction. J Chem Phys. 2014; 141(12):124118. DOI: 10.1063/1.4896229. View

16.

Tonnele C, Champagne B, Muccioli L, Castet F . Second-order nonlinear optical properties of Stenhouse photoswitches: insights from density functional theory. Phys Chem Chem Phys. 2018; 20(43):27658-27667. DOI: 10.1039/c8cp05843a. View

17.

Rtibi E, Abderrabba M, Ayadi S, Champagne B . Theoretical Assessment of the Second-Order Nonlinear Optical Responses of Lindqvist-Type Organoimido Polyoxometalates. Inorg Chem. 2019; 58(16):11210-11219. DOI: 10.1021/acs.inorgchem.9b01857. View