Citation: SHI Yufang, SUN Jinyu, LIU Chengqi, ZHAO Minggen. Synthesis and Third-order Nonlinear Optical Property of 1-(Pyrene-1-yl)-3-(4-methoxyphenyl)acrylic Ketone[J]. Chinese Journal of Applied Chemistry, ;2016, 33(2): 149-154. doi: 10.11944/j.issn.1000-0518.2016.02.150216 shu

Synthesis and Third-order Nonlinear Optical Property of 1-(Pyrene-1-yl)-3-(4-methoxyphenyl)acrylic Ketone

1.
Shanxi Province Key Laboratory for Materials and ComputationalChemistry, Department of Chemistry, Xinzhou Teachers University, Xinzhou, Shanxi 034000, China

Corresponding author: ZHAO Minggen,
Received Date: 29 June 2015
Available Online: 13 November 2015
Fund Project:

A new nonlinear optical(NLO) organic material 1-(pyrene-1-yl)-3-(4-methoxyphenyl)acrylic ketone(PMPAK) was synthesized and characterized with ¹H NMR, IR, HR-MS and elemental analysis. The three order NLO properties of PMPAK was tested by 4f phase-coherent imaging system which utilized Nd:YAG-Laser System as the light source. The laser pulse was set at the wavelength of 450 nm with the pulse duration of 4 ns(FWHM), thus the relevant parameters were determined as: the nonlinear refractive index n₂=-1.84×10^-16 m²/W, the nonlinear absorption coefficient β=2.53×10^-9 m/W and the third-order nonlinear polarizability χ⁽³⁾=1.137×10^-10 esu.
- pyrene derivatives,
- Chalcone,
- (pyrene-yl)-(methoxyphenyl)acrylic ketone,
- synthesis,
- nonlinear optical properties
1. [1]
  [1] Hemaraju B C,Ahlam M A,Pushpa N,et al. Synthesis, Growth and Characterization of a New Promising Organic Nonlinear Optical Crystal: 4-Nitrophenyl Hydrazone[J]. Spectrochim Acta,Part A,2015,151(7):854-860.
2. [2]
  [2] SUN Jing,FAN Heliang,WANG Xinqiang,et al. Study on Optical Limiting Property of Organometallic Compound[J]. Chinese J Lasers,2009,36(9):2417-2421(in Chinese).孙晶,范贺良,王新强,等. 一种金属有机配合物的光限幅性质研究[J]. 中国激光,2009,36(9):2417-2421.
3. [3]
  [3] Prabhu A N,Jayarama A,Subrahmanya B K,et al. Growth, Characterization and Structural Investigation of a Novel Nonlinear Optical Crystal[J]. J Mol Struct,2013,1031(1):79-84.
4. [4]
  [4] Seung Koo Parka,Jung Yun Dob,Jung Jin Jua,et al. Nonlinear Optical Polymer Applicable for All-optical Wavelength Converters in Communications Bands Near 1.5 μm[J]. Mater Lett,2005,59:2872-2875.
5. [5]
  [5] Thangaraj M,Vinitha G,Sabari Girisun T C,et al. Third Order Nonlinear Optical Properties and Optical Limiting Behavior of Alkali Metal Complexes of p-Nitrophenol[J]. Opt Laser Technol,2015,73(5):130-134.
6. [6]
  [6] Bugaychuki S,Klimusheva G,Garbovskiy Y,et al. Nonlinear Optical Properties of Composites Based on Conductive Metal-alkanoate Liquid Crystals[J]. Opto-Electron Rev,2006,14(4):275-279.
7. [7]
  [7] Champagne B,Plaquet A,Pozzo J L,et al. Nonlinear Optical Molecular Switches as Selective Cation Sensors[J]. J Am Chem Soc,2012,134(5):8101-8103.
8. [8]
  [8] Qin Z B,Wen Y Q,Shang Y L,et al. Study of an Organic Nonlinear Optical Material for Nanoscale Data Sorage by Scanning Tunneling Microscope[J]. Appl Phys A,2007,87(1):277-280.
9. [9]
  [9] Wang L,Fang Q,Lu Q,et al. Octupolar(C₃ and S₄) Symmetric Cyclized Indole Derivatives:Syntheses, Structures, and NLO Properties[J]. Org Lett,2015,17(8):4164-4167.
10. [10]
  [10] Oudar J L. Optical Nonlinearities of Conjugated Molecules. Stilbene Derivatives and Highly Polar Aromatic Compounds[J]. J Chem Phys,1977,67(2): 446-457.
11. [11]
  [11] Harrison W T A,Yathirajan H S,Anilkumar H G,et al. 1-(4-Fluoro phen yl)-3-(4-methoxy phen yl)prop-2-en-1-one[J]. Acta Crystallogr E,2006,62:o3251-o3253.
12. [12]
  [12] Harrison W T A,Yathirajan H S,Sarojini B K,et al. 2-Bromo-1-chlorophenyl-3-(4-methoxy phen yl)prop-2-en-1-one[J]. Acta Crystallogr E,2006,62:o1578-o1579.
13. [13]
  [13] Harrison W T A,Ashalatha B V,Narayana B,et al. (2E)-1-(3-Bromo-2-thienyl)-3-(4-nitrophenyl)prop-2-en-1-one[J]. Acta Crystallogr E,2007,63:o4183.
14. [14]
  [14] LIU Yuting,Fu Quejun,Yin Dawei,et al. The New Research Development of Functional Ferrocene Material[J]. New Chem Mater,2009,37(3):27-29(in Chinese).刘玉婷,傅雀军,尹大为,等. 含二茂铁功能材料的最新研究进展[J]. 化工新型材料,2009,37(3):27-29.
15. [15]
  [15] Nakano M,Kishi R,Yoneda K,et al. Third-Order Nonlinear Optical Properties of Open-Shell Supermolecular Systems Composed of Acetylene Linked Phenalenyl Radicals[J]. J Phys Chem A,2011,115(31):8767-8777.
16. [16]
  [16] SHENG Ning. Synthesis and Third-order Nonlinear Optical Property of Novel Pyrene Derivatives[J]. J Jining Univ,2013,34(3):9-10,15(in Chinese).盛宁. 芘衍生物的三阶非线性光学性质研究[J]. 济宁学院学报,2013,34(3):9-10,15.
17. [17]
  [17] Weng J N,Mei Q B,Ling Q D,et al. A New Colorimetric and Fluorescent Ratiometric Sensor for Hg²⁺ Based on 4-Pyren-1-yl-pyrimidine[J]. Tetrahedron,2012,68(1):3129-3134.
18. [18]
  [18] Beck A D. Density Functional Thermochemistry.Ⅲ.The Role of Exact Exchange[J]. J Chem Phys,1993,98(7):5648-5659.
19. [19]
  [19] Lee C,Yang W,Parr R G. Development of the Colle-Salvetti Correlation-energy Formula into a Functional of the Electron Density[J]. Phys Rev B,1988,37(2):785-791.
20. [20]
  [20] Frisch M J,Trucks G W,Schlegel H B,et al. Gaussian 03,Revision A.l,Gaussian,Inc.,Pittsburgh PA,2009.
21. [21]
  [21] Shui M,Jin X,Yang J Y,et al. Third-Order Nonlinearity Measurements of PbPc(CP)₄/DMF[J]. J Opt,2010,12(9):582-591.
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