Abstract
Chalcones have gained attention due to their wide range of biological activities, including anticancer, antimalarial, antimicrobial, antitubercular, antimutagenic, anti-inflammatory, and anti-diabetic effects, as well as their physical properties on nonlinear optical materials. This work describes the synthesis and extensive characterization of a new chalcone (2E)-3-(4-hydroxyphenyl)-1-(4-methylphenyl)prop-2-en-1-one. Single crystal X-ray diffraction and Hirshfeld surfaces were employed to analyze the molecular structure and supramolecular arrangement (stabilized primarily by O2–H2⋯O1 and C15–H15⋯O1 hydrogen bonds). The frontier molecular orbitals and molecular electrostatic potential maps were obtained to predict the chemical reactivity properties. The structured media supermolecule approach reaffirms its accuracy in gauging the dipole moment of crystals during their electric polarization processes. The significant shifts observed in molecular optical behaviors when placed within crystalline environments reinforce the impactful role of surroundings on both electrical and optical properties. This paper not only sheds light on the unique properties of the title compound but also underscores the potential applications of chalcones in both biological and material sciences.
Graphical abstract
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Abegão LMG, Santos FA, Fonseca RD et al (2020) Chalcone-based molecules: experimental and theoretical studies on the two-photon absorption and molecular first hyperpolarizability. Spectrochim Acta A Mol Biomol Spectrosc 227:117772. https://doi.org/10.1016/j.saa.2019.117772
Aditya Prasad A, Muthu K, Meenatchi V et al (2015) Optical, vibrational, NBO, first-order molecular hyperpolarizability and Hirshfeld surface analysis of a nonlinear optical chalcone. Spectrochim Acta A Mol Biomol Spectrosc 140:311–327. https://doi.org/10.1016/j.saa.2014.12.011
Aguiar ASN, dos Santos VD, Borges ID et al (2022) Bromine substitution effect on structure, reactivity, and linear and third-order nonlinear optical properties of 2,3-dimethoxybenzaldehyde. J Phys Chem A 126:7852–7863. https://doi.org/10.1021/acs.jpca.2c04658
Aguiar ASN, Dias PGM, Queiroz JE et al (2023) Insights on potential photoprotective activity of two butylchalcone derivatives: synthesis, spectroscopic characterization and molecular modeling. Photonics 10:228. https://doi.org/10.3390/photonics10030228
Al-Jaber NA, Bougasim ASA, Karah MMS (2012) Study of Michael addition on chalcones and or chalcone analogues. J Saudi Chem Soc 16:45–53. https://doi.org/10.1016/j.jscs.2010.10.017
Arshad MN, Al-Dies A-AM, Asiri AM et al (2017) Synthesis, crystal structures, spectroscopic and nonlinear optical properties of chalcone derivatives: a combined experimental and theoretical study. J Mol Struct 1141:142–156. https://doi.org/10.1016/j.molstruc.2017.03.090
Barbosa MR, Costa ISD, Lopes TO et al (2022) Theoretical model of polarization effects on third-order NLO properties of the stilbazolium derivative crystal. J Phys Chem A 126:8901–8909. https://doi.org/10.1021/acs.jpca.2c04214
Bauernschmitt R, Ahlrichs R (1996) Treatment of electronic excitations within the adiabatic approximation of time dependent density functional theory. Chem Phys Lett 256:454–464. https://doi.org/10.1016/0009-2614(96)00440-X
Bell AJ, Sejnowski TJ (1995) A nonlinear information maximization algorithm that performs blind separation. In Advances in Neural Information Processing Systems 7, G. Tesauro et al., eds., pp. 467-474. MIT Press, Cambridge, MA.
Briseno AL, Mannsfeld SCB, Reese C et al (2007) Perylenediimide nanowires and their use in fabricating field-effect transistors and complementary inverters. Nano Lett 7:2847–2853. https://doi.org/10.1021/nl071495u
Bruno IJ, Cole JC, Kessler M et al (2004) Retrieval of crystallographically-derived molecular geometry information. J Chem Inf Comput Sci 44:2133–2144. https://doi.org/10.1021/ci049780b
Castro AN, Almeida LR, Anjos MM et al (2016) Theoretical study on the third-order nonlinear optical properties and structural characterization of 3-acetyl-6-bromocoumarin. Chem Phys Lett 653:122–130. https://doi.org/10.1016/j.cplett.2016.04.070
Custodio J, Moreira C, Valverde C et al (2017) Hirshfeld surfaces and nonlinear optics on two conformers of a heterocyclic chalcone. J Braz Chem Soc. https://doi.org/10.21577/0103-5053.20170136
Custodio JMF, D’Oliveira GDC, Gotardo F et al (2021) Second-order nonlinear optical properties of two chalcone derivatives: insights from sum-over-states. Phys Chem Chem Phys 23:6128–6140. https://doi.org/10.1039/D0CP06469F
Custodio JMF, Fernandes FS, Vaz WF et al (2022) Relating the crystal structure and third-order nonlinear susceptibility of a new Neolignan derivative. J Mol Struct 1249:131566. https://doi.org/10.1016/j.molstruc.2021.131566
D’silva ED, Podagatlapalli GK, Venugopal Rao S, Dharmaprakash SM (2012) Study on third-order nonlinear optical properties of 4-methylsulfanyl chalcone derivatives using picosecond pulses. Mater Res Bull 47:3552–3557. https://doi.org/10.1016/j.materresbull.2012.06.063
Dennington R, Keith TA, Millam JM (2016) GaussView, Version 6, Roy Dennington, Todd A. Keith, and John M. Millam, Semichem Inc., Shawnee Mission, KS
Dolomanov OV, Bourhis LJ, Gildea RJ et al (2009) OLEX2: a complete structure solution, refinement and analysis program. J Appl Crystallogr 42:339–341. https://doi.org/10.1107/S0021889808042726
Domingo LR, Aurell MJ, Pérez P, Contreras R (2002) Quantitative characterization of the global electrophilicity power of common diene/dienophile pairs in Diels-Alder reactions. Tetrahedron 58:4417–4423. https://doi.org/10.1016/S0040-4020(02)00410-6
Frisch MJ, Trucks GW, Schlegel HB et al (2016) Gaussian 16, revision C.01. Gaussian Inc., Wallingford
Fukui K (1979) (1982) Role of frontier orbitals in chemical reactions. Science 218:747–754. https://doi.org/10.1126/science.218.4574.747
Guha S, Majumdar D, Bhattacharjee AK (1992) Molecular electrostatic potential: a tool for the prediction of the pharmacophoric pattern of drug molecules. J Mol Struct (theochem) 256:61–74. https://doi.org/10.1016/0166-1280(92)87158-V
Günter P (2000) Nonlinear optical effects and materials. Springer, Berlin Heidelberg, Berlin, Heidelberg
Gupta D, Jain D (2015) Chalcone derivatives as potential antifungal agents: Synthesis, and antifungal activity. J Adv Pharm Technol Res 6:114. https://doi.org/10.4103/2231-4040.161507
Hohenberg P, Kohn W (1964) Inhomogeneous electron gas. Phys Rev 136:B864. https://doi.org/10.1103/PhysRev.136.B864
Hussein HA (2023) A DFT study of structural-stability, Mulliken charges, MEP, FMO, and NLO properties of trans alkenyl substituted chalcones conformers: theoretical study. Struct Chem 34:2201–2223. https://doi.org/10.1007/s11224-023-02139-7
Iwan A, Sek D (2011) Polymers with triphenylamine units: photonic and electroactive materials. Prog Polym Sci 36:1277–1325. https://doi.org/10.1016/j.progpolymsci.2011.05.001
Jazbinsek M, Mutter L, Gunter P (2008) Photonic applications with the organic nonlinear optical crystal DAST. IEEE J Sel Top Quantum Electron 14:1298–1311. https://doi.org/10.1109/JSTQE.2008.921407
John Kiran A, Mithun A, Shivarama Holla B et al (2007) Nonlinear optical studies of 1–3-diaryl-propenones containing 4-methylthiophenyl moieties. Opt Commun 269:235–240. https://doi.org/10.1016/j.optcom.2006.07.073
Kaya İ, Yıldırım M, Avcı A (2010) Synthesis and characterization of fluorescent polyphenol species derived from methyl substituted aminopyridine based Schiff bases: the effect of substituent position on optical, electrical, electrochemical, and fluorescence properties. Synth Met 160:911–920. https://doi.org/10.1016/j.synthmet.2010.01.044
Kohn W, Sham LJ (1965) Self-consistent equations including exchange and correlation effects. Phys Rev 140:A1133–A1138. https://doi.org/10.1103/PhysRev.140.A1133
Kong L-Y, Li Z-W, Okamura T et al (2005) Synthesis, structure and optical limiting property of CoII, MnII and CdII complexes with di-Schiff base and reduced di-Schiff base ligands. Chem Phys Lett 416:176–181. https://doi.org/10.1016/j.cplett.2005.09.074
Li Y, Evans JNS (1995) The Fukui function: a key concept linking frontier molecular orbital theory and the hard-soft-acid-base principle. J Am Chem Soc 117:7756–7759. https://doi.org/10.1021/ja00134a021
Marenich AV, Cramer CJ, Truhlar DG (2009) Universal solvation model based on solute electron density and on a continuum model of the solvent defined by the bulk dielectric constant and atomic surface tensions. J Phys Chem B 113:6378–6396. https://doi.org/10.1021/jp810292n
McKinnon JJ, Jayatilaka D, Spackman MA (2007) Towards quantitative analysis of intermolecular interactions with Hirshfeld surfaces. Chem Commun. https://doi.org/10.1039/b704980c
Mellado M, Madrid A, Martınez U, Mella J, Salas CO (2018) Hansch’s analysis application to chalcone synthesis by Claisen–Schmidt reaction based in DFT methodology. Chem Pap 72:703–709. https://doi.org/10.1007/s11696-017-0316-3
Menezes AP, Jayarama A, Ng SW (2015) Crucial role of molecular planarity on the second order nonlinear optical property of pyridine based chalcone single crystals. J Mol Struct 1088:85–94. https://doi.org/10.1016/j.molstruc.2015.02.011
Muhammad S, Al-Sehemi AG, Su Z et al (2017) First principles study for the key electronic, optical and nonlinear optical properties of novel donor-acceptor chalcones. J Mol Graph Model 72:58–69. https://doi.org/10.1016/j.jmgm.2016.12.009
Murthy PK, Sheena Mary Y, Shyma Mary Y et al (2017) Synthesis, crystal structure analysis, spectral investigations, DFT computations and molecular dynamics and docking study of 4-benzyl-5-oxomorpholine-3-carbamide, a potential bioactive agent. J Mol Struct 1134:25–39. https://doi.org/10.1016/j.molstruc.2016.12.037
Niu H-J, Huang Y-D, Bai X-D, Li X (2004) Novel poly-Schiff bases containing 4,4′-diamino-triphenylamine as hole transport material for organic electronic device. Mater Lett 58:2979–2983. https://doi.org/10.1016/j.matlet.2004.05.007
Noviany HO, Mohamad S (2015) Synthesis and biological evaluation of 2′-hydroxy-retro-chalcone derivatives as antituberculosis agent. J Chem Pharm Res 6:114–117
Omar S, Mohd S, Ajmal Khan M et al (2020) A comprehensive study on molecular geometry, optical, HOMO-LUMO, and nonlinear properties of 1,3-diphenyl-2-propen-1-ones chalcone and its derivatives for optoelectronic applications: a computational approach. Optik (stuttg) 204:164172. https://doi.org/10.1016/j.ijleo.2020.164172
Parr RG, Szentpály LV, Liu S (1999) Electrophilicity index. J Am Chem Soc 121:1922–1924. https://doi.org/10.1021/ja983494x
Pearson RG (1992) The electronic chemical potential and chemical hardness. J Mol Struct (theochem) 255:261–270. https://doi.org/10.1016/0166-1280(92)85014-C
Pearson RG (2005) Chemical hardness and density functional theory. J Chem Sci 117:369–377. https://doi.org/10.1007/BF02708340
Pérez P, Domingo LR, José Aurell M, Contreras R (2003) Quantitative characterization of the global electrophilicity pattern of some reagents involved in 1,3-dipolar cycloaddition reactions. Tetrahedron 59:3117–3125. https://doi.org/10.1016/S0040-4020(03)00374-0
Polisseni C, Major KD, Boissier S et al (2016) Stable, single-photon emitter in a thin organic crystal for application to quantum-photonic devices. Opt Express 24:5615. https://doi.org/10.1364/OE.24.005615
Politzer P, Murray JS (2002) The fundamental nature and role of the electrostatic potential in atoms and molecules. Theor Chem Acc 108:134–142. https://doi.org/10.1007/s00214-002-0363-9
Poojith N, Rani NU, Potla KM et al (2021) An analysis of structural, spectroscopic, quantum chemical and in silico studies of ethyl 3-[(pyridin-2-yl)amino]propanoate: a potential thrombin inhibitor. J Mol Struct 1226:129378. https://doi.org/10.1016/j.molstruc.2020.129378
Prabhu AN, Upadhyaya V, Jayarama A, Bhat KS (2016) Third-order NLO property of thienyl chalcone derivative: physicochemical analysis and crystal structure determination. Mol Cryst Liq Cryst 637:76–86. https://doi.org/10.1080/15421406.2016.1177921
Puschmann H, Dolomanov O, Bourhis L et al (2011) Olex2—a complete package for molecular crystallography. Acta Crystallogr 67:C593. https://doi.org/10.1107/S0108767311084996
Safari J, Gandomi-Ravandi S (2014) Structure, synthesis and application of azines: a historical perspective. RSC Adv 4:46224–46249. https://doi.org/10.1039/C4RA04870A
Sallum LO, Valverde C, Andrade IL et al (2022) Molecular modeling and nonlinear optical properties of new isostructural halogenated dihydroquinolinones. New J Chem 46:14192–14204. https://doi.org/10.1039/d2nj00501h
Sheikhshoaie I, Fabian W (2006) Quantum chemical study on the electronic structure and second-order nonlinear optical properties of salen-type Schiff bases. Dyes Pigm 70:91–98. https://doi.org/10.1016/j.dyepig.2005.04.011
Sheldrick GM (2008) A short history of SHELX. Acta Crystallogr A 64:112–122. https://doi.org/10.1107/S0108767307043930
Sheldrick GM et al (2015) Crystal structure refinement with SHELXL. Acta Crystallogr C Struct Chem 71:3–8. https://doi.org/10.1107/S2053229614024218
Shettigar S, Chandrasekharan K, Umesh G et al (2006) Studies on nonlinear optical parameters of bis-chalcone derivatives doped polymer. Polymer (guildf) 47:3565–3567. https://doi.org/10.1016/j.polymer.2006.03.062
Shettigar S, Umesh G, Chandrasekharan K et al (2008) Studies on third-order nonlinear optical properties of chalcone derivatives in polymer host. Opt Mater (amst) 30:1297–1303. https://doi.org/10.1016/j.optmat.2007.06.008
Spackman MA, Jayatilaka D (2009) Hirshfeld surface analysis. CrystEngComm 11:19–32. https://doi.org/10.1039/B818330A
Spackman MA, McKinnon JJ (2002) Fingerprinting intermolecular interactions in molecular crystals. CrystEngComm 4:378–392. https://doi.org/10.1039/b203191b
Spackman PR, Turner MJ, McKinnon JJ et al (2021) CrystalExplorer: a program for Hirshfeld surface analysis, visualization and quantitative analysis of molecular crystals. J Appl Crystallogr 54:1006–1011. https://doi.org/10.1107/S1600576721002910
Sun W, McKerns MM, Lawson CM et al (2000) Solvent effect on the third-order nonlinearity and optical limiting ability of a stilbazolium-like dye, p 280
Tan L, Jiang W, Jiang L et al (2009) Single crystalline microribbons of perylo[1,12-b, c, d]selenophene for high performance transistors. Appl Phys Lett 94:153306. https://doi.org/10.1063/1.3120769
Valverde C, Vinhal RS, Naves LFN et al (2022) Remarkable nonlinear properties of a novel quinolidone derivative: joint synthesis and molecular modeling. Molecules 27:2379. https://doi.org/10.3390/molecules27082379
Vaz WF, Custodio JMF, Silveira RG et al (2016) Synthesis, characterization, and third-order nonlinear optical properties of a new neolignane analogue. RSC Adv 6:79215–79227. https://doi.org/10.1039/C6RA14961H
Weinstein H, Osman R, Green JP, Topiol S (1981) Electrostatic potentials as descriptors of molecular reactivity: the basis for some successful predictions of biological activity. Chemical applications of atomic and molecular electrostatic potentials. Springer, US, Boston, MA, pp 309–334
Winter C, Caetano JN, Araújo ABC et al (2016) Activated carbons for chalcone production: Claisen–Schmidt condensation reaction. Chem Eng J 303:604–610. https://doi.org/10.1016/j.cej.2016.06.058
Yanai T, Tew DP, Handy NC (2004a) A new hybrid exchange–correlation functional using the Coulomb-attenuating method (CAM-B3LYP). Chem Phys Lett 393:51–57. https://doi.org/10.1016/j.cplett.2004.06.011
Yanai T, Tew DP, Handy NC (2004b) A new hybrid exchange-correlation functional using the Coulomb-attenuating method (CAM-B3LYP). Chem Phys Lett 393:51–57. https://doi.org/10.1016/j.cplett.2004.06.011
Zhang J, Lu T (2021) Efficient evaluation of electrostatic potential with computerized optimized code. Phys Chem Chem Phys 23:20323. https://doi.org/10.1039/D1CP02805G
Zhang G, Musgrave CB (2007) Comparison of DFT methods for molecular orbital eigenvalue calculations. J Phys Chem A 111:1554–1561. https://doi.org/10.1021/jp061633o
Zhang L, Pavlica E, Zhong X et al (2017) Fast-response photonic device based on organic-crystal heterojunctions assembled into a vertical-yet-open asymmetric architecture. Adv Mater 29:1605760. https://doi.org/10.1002/adma.201605760
Acknowledgements
The authors are grateful for the financial support of the Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq), Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES), Fundação Nacional de Desenvolvimento do Ensino Superior Particular (FUNADESP), and Fundação de Amparo à Pesquisa de Goiás (FAPEG), Brazil. Research developed with the support of the Centro de Computação de Alto Desempenho da Universidade Estadual de Goiás (UEG) and Centro de Análises, Inovação e Tecnologia da UEG (CAiTec).
Author information
Authors and Affiliations
Contributions
Luiz B. Costa, Loides O. Sallum, and Jean M. F. Custodio were responsible for analyzing the crystalline state; Cristiane A. F. E. Santos and Clodoaldo Valverde were responsible for the calculations and analyses of nonlinear optical properties; Jaqueline E. Queiroz and Gilberto L. B. Aquino synthesized and elucidated the compound; Antônio S. N. Aguiar and Ademir J. Camargo were responsible for molecular modeling calculations, analysis of chemical reactivity descriptors, and electronic transitions of the compound; Hamilton B. Napolitano, Ademir J. Camargo, Clodoaldo Valverde, and Antônio S. N. Aguiar were responsible for reviewing and editing the draft. All authors have read and agreed to the final version of the manuscript.
Corresponding authors
Ethics declarations
Conflict of interest
The authors declare no competing interests.
Additional information
Publisher's Note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Supplementary Information
Below is the link to the electronic supplementary material.
Rights and permissions
Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.
About this article
Cite this article
Costa, L.B., Santos, C.A.F.E., Queiroz, J.E. et al. Synthesis, characterization, and supramolecular analysis of a novel chalcone derivative: exploring nonlinear optical applications. Rend. Fis. Acc. Lincei 35, 131–147 (2024). https://doi.org/10.1007/s12210-024-01238-9
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s12210-024-01238-9