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Naresh, P., Mahesha, Vinuth Raj, T. N., Naveen, S., Deepa Urs, M. V., Sunitha, K., Subham Kumar, V., Lokanath, N. K., Ganguly, S., Panda, J., Banerjee, D. 
ORCID: https://orcid.org/0000-0003-4066-8112 and Venugopal Rao, S.
(2025)
Design, crystal insights, and non-linear optical properties of a novel methoxy-substituted thiophene chalcone:A theoretical and experimental approach.
Journal of Molecular Structure, 1333.
pp. 1-12.
ISSN 0022-2860
Abstract
A comprehensive study was conducted to investigate the supramolecular assembly, molecular structural characteristics, and a quantitative evaluation of the non-covalent interaction energies of a halogenated chalcone molecule. By exposing the reaction mixture to ultrasonic irradiation at room temperature, the compound (E)-1-(5-bromothiophen-2-yl)-3-(3,4-dimethoxyphenyl)prop‑2-en-1-one was synthesized. The slow evaporation method was used to achieve crystallization, which made it easier to analyze the supramolecular, physicochemical, and structural properties using single-crystal X-ray diffraction and DFT studies. Additionally, mass spectrometry, nuclear magnetic resonance (NMR), and Fourier-transform infrared (FTIR) spectroscopy were used to analyze the structural arrangements of the synthesized molecule. The molecule, which possesses a chalcone group, has a trans configuration because of the C6=C7 double bond, according to the crystal structure analysis. A petite dihedral angle of 5.11° between the phenyl and thiophene rings confirmed the molecule's planarity. The investigation of supramolecular characteristics highlighted the importance of weak C[sbnd]H-O hydrogen bonds, which entail the carbonyl group and substituted dimethoxy moiety as hydrogen bond acceptors. Furthermore, it was discovered that the C-Br-O-C and C[sbnd]H-π interactions were significant. The electrostatic, polarization, dispersion, and repulsive energy components that contribute to the paired molecular interaction energies were also quantitatively analyzed. The DFT approach measured the molecule's HOMO-LUMO energy band gap to be 3.4779 eV. The title molecule and a similar chalcone-thiophene derivative, (2E)-1-(5-bromothiophen-2-yl)-3-(4-methoxyphenyl)prop‑2-en-1-one (1,897,986), which was taken from the Cambridge Structural Database, were compared. This investigation was conducted to determine how various substituents affected the 3,4-dimethoxy-benzaldehyde's phenyl ring.
| Item Type: | Article |
|---|---|
| Additional Information: | Data availability The data that has been used is confidential. Acknowledgements The authors are grateful to the National Single Crystal Diffractometer Facility, Department of Studies in Physics, University of Mysore, Manasagangotri, Mysuru for providing the X-ray intensity data and JAIN (Deemed-to-be University) for sanctioning the funds under the minor project JU/MRP/SET/7/2022. The authors additionally acknowledge Prof. D. B. Ramachary of the University of Hyderabad’s, School of Chemistry for his assistance in crystallizing the compound as well as Prof. B. V. R. Tata Rao of GITAM University for his ongoing support in conducting the z-scan. |
| Uncontrolled Keywords: | chalcone,dft studies,energy framework,hirshfeld surface analysis,nci-rdg,x-ray diffraction,analytical chemistry,spectroscopy,organic chemistry,inorganic chemistry ,/dk/atira/pure/subjectarea/asjc/1600/1602 |
| Faculty \ School: | Faculty of Science > School of Chemistry, Pharmacy and Pharmacology |
| Related URLs: | |
| Depositing User: | LivePure Connector |
| Date Deposited: | 04 Sep 2026 12:53 |
| Last Modified: | 09 Sep 2026 16:47 |
| URI: | https://ueaeprints.uea.ac.uk/id/eprint/104427 |
| DOI: | 10.1016/j.molstruc.2025.141737 |
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