Synthesis and Third-Order Nonlinear Optical Properties of Fluorinated Aromatic Chalcone Derivatives

doi:10.19894/j.issn.1000-0518.240208

Chinese Journal of Applied Chemistry ›› 2025, Vol. 42 ›› Issue (1): 86-94.DOI: 10.19894/j.issn.1000-0518.240208

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Synthesis and Third-Order Nonlinear Optical Properties of Fluorinated Aromatic Chalcone Derivatives

Gui-Lin WANG¹, Jian-Feng HAO², Yu-Fang SHI¹(), Ying-Jin WANG¹, Ming-Gen ZHAO¹

^1.Key Laboratory of Materials and Computational Chemistry，Department of Chemistry，Xinzhou Normal University，Xinzhou 034000，China
^2.Road Traffic Safety Education Center，Xinzhou City Public Security Bureau，Xinzhou 034000，China

Received:2024-07-11 Accepted:2024-10-31 Published:2025-01-01 Online:2025-01-24
Contact: Yu-Fang SHI
About author:yfshi868@163.com
Supported by:
the Project of Science and Technology Bureau of Xinzhou City, Shanxi Province(20230511)

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Abstract

Abstract:

Four novel chalcone derivatives were synthesized： 1-（2，3-difluorophenyl）-3-（3-chloro thiophene-2-yl）-2-propene-1-ketone （0208#）， 1-（2，4-difluorophenyl）-3-（5-phenylthiophene-2-yl）-2-propene-1-ketone （0809#）， 1-（2，3-difluorophenyl）-3-（5-phenylthiophene-2-yl）-2-propene-1-ketone （0808#）， 1-（2，6-difluorophenyl）-3-（5-phenylthiophene-2-yl）-2-propene-1-ketone （0812#）. The structures and properties of the compounds were characterized by ¹H NMR， ¹³C NMR， liquid chromatography-mass spectrometry， ultraviolet-visible spectrum （UV-Vis） absorption spectrum， fluorescence emission （EM） spectrum and Z-scanning technique. The energy and polarizability of the highest occupied molecular orbitals （HOMO） and the lowest unoccupied molecular orbital （LUMO） of the four compounds were obtained by density functional theory， and significant intramolecular charge transfer was found from orbital electron cloud images. The combination of large π-conjugation and charge transfer makes the four aryl chalcone derivatives exhibit good nonlinear optical properties. They can be used as useful candidates for nonlinear absorption （NLA） and have potential applications.

Key words: Chalcone derivatives, Theoretical calculation, Optical properties

CLC Number:

O625.4

Gui-Lin WANG, Jian-Feng HAO, Yu-Fang SHI, Ying-Jin WANG, Ming-Gen ZHAO. Synthesis and Third-Order Nonlinear Optical Properties of Fluorinated Aromatic Chalcone Derivatives[J]. Chinese Journal of Applied Chemistry, 2025, 42(1): 86-94.

Figures/Tables 6

Fig.1 Synthetic route of 1-（2，3-difluorophenyl）-3-（3-chlorothiophene-2-yl）-2-propene-1-ketone

Fig.2 Synthetic route of three fluorinated aromatic chalcone derivatives

Fig.3 UV-Vis absorption spectra （A） and fluorescence emission spectra （B） of four compounds （1.0×10-5 mol/L）

Table 1 Molecular orbital energy and polarization of four compounds

Compounds	E_HOMO/eV	E_LUMO/eV	ΔE_LUMO-HOMO/eV	α（polarization）/a.u.
0208#	-6.83	-2.76	4.07	199.14
0809#	-6.13	-2.81	3.32	325.85
0808#	-6.12	-2.77	3.35	299.96
0812#	-6.13	-2.73	3.40	295.17

Table 2 Third-order nonlinear optical absorption and refraction of four compounds

Compounds	Pulse width/ps	λ/nm	Absorption coefficient 10¹³β/（m·W^-1）	Refraction coefficient 10¹⁹γ/esu
0208#	20	532	1.7	1.2
0809#	20	532	2.5	1.8
0808#	20	532	2.3	1.6
0812#	20	532	2.2	1.4

Fig.4 Z-scan curves of four compounds（left： open-aperture； right： closed-aperture）

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Synthesis and Third-Order Nonlinear Optical Properties of Fluorinated Aromatic Chalcone Derivatives

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