含咔唑生色团的有机芳香杂环分子的二阶非线性光学性质

doi:10.3866/PKU.WHXB20110316

Abstract

Abstract:

Density functional theory (DFT) B3LYP/6-31G^* method was used to optimize the geometrical structures of a series of heteroaromatic molecules with carbazole chromophores. The second-order nonlinear optical (NLO) properties and electronic spectra were then studied by finite field (FF) and time-dependent DFT (TD-DFT) methods at the 6-311G^** level. The results showed that the polarizability α and the second-order NLO coefficient β values of all molecules were influenced greatly by the change of the push-pull electronic ability of the carbazole substituent groups and the introduction of heteroaromatic. When the pull electronic nitro and the push electronic hydroxyl were linked by carbazole substituent groups respectively and the furan heterocycle was introduced, the β values decreased (blue-shifted) with an increase in the maximum absorption wavelengths λ_max of the molecules. The “nonlinear-transparency tradeoff” conflict was avoided because of the high second-order NLO responses and good transparency. All the compounds may have potential application in the development of NLO materials.

Key words: Density functional theory, Carbazole, Second-order nonlinear optical property, Electronic spectrum

MSC2000:

O641

ZHAO Min, ZHANG Yuan, WANG Lu. Second-Order Nonlinear Optical Properties of Organic Heteroaromatic Molecules with Carbazole Chromophores[J].Acta Phys. -Chim. Sin., 2011, 27(03): 584-588.

References

(1) Geskin, V. M.; Lambert, C.; Bredas, J. L. J. Am. Chem. Soc. 2003, 125, 15651.
(2) Andreu, R.; Blesa, M. J.; Carrasquer, L.; Garin, J.; Orduna, J.; Villacampa, B.; Alcala, R.; Casado, J.; Delgado, M. C. R.; Navarrete, J. T. L.; Allain, M. J. Am. Chem. Soc. 2005, 127, 8835.
(3) Humphrey, J. L.; Lott, K. M.; Wright, M. E.; Duciauskas, D. J. Phys. Chem. B 2005, 109, 21496.
(4) Liu, C. G.; Qiu, Y. Q.; Su, Z. M.; Yang, G. C.; Sun, S. L. J. Phys. Chem. C 2008, 112, 7021.
(5) Rao, V. P.; Jen, A. K. Y.; Wong, K. Y.; Drost, K. J. Tetrahedron Lett. 1993, 34, 1747.
(6) Hsu, C. C.; Shu, C. F.; Huang, T. H.; Wang, C. H.; Lin, J. L.; Wang, Y. K.; Zang, Y. L. Chem. Phys. Lett. 1997, 274, 466.
(7) Bai, H. T.; Lin, H. C.; Luh, T. Y. J. Org. Chem. 2010, 75, 4591.
(8) Umeyama, T.; Takamatsu, T.; Tezuka, N.; Matano, Y.; Araki, Y.; Wada, T.; Yoshikawa, O.; Sagawa, T.; Yoshikawa, S.; Imahori, H. J. Phys. Chem. C 2009, 113, 10798.
(9) Li, Q. Q.; Lu, C. G.; Zhu, J.; Fu, E. Q.; Zhong, C.; Li, S. Y.; Cui, Y. P.; Qin, J. G.; Li, Z. J. Phys. Chem. B 2008, 112, 4545.
(10) Christopher, R. M.; Brian, J. M.; Lawrence, C. N.; Michael, A. M.; Eric L, H.; Benjamin A, B. J. Org. Chem. 2004, 69, 8239.
(11) Ma, J.; Li, S.; Jiang, Y. Macromolecules 2002, 35, 1109.
(12) Dalton, L.; Davies, J.; Elangovan, A.; Sullivan, P. J. Am. Chem. Soc. 2008, 130, 10565.
(13) Song, N. H.; Ma, X. H.; Liang, R.; Yang, F.; Zhao, Z. H.; Zhang, A. X.; Zhou, Q. F.; Zhang, J. P. J. Mater. Chem. 2008, 18, 1756.
(14) Qian, Y. Dyes Pigments 2008, 76, 277.
(15) Albert, D. L.; Marks, T. J.; Ratner, M. A. J. Am. Chem. Soc. 1997, 119, 6575.
(16) Luo, S. S.; Qiu, Y. Q.; Liu, X. D.; Liu, C. G.; Su, Z. M. Acta Phys. -Chim. Sin. 2009, 25, 1867.
[罗姗姗, 仇永清, 刘晓东, 刘春光, 苏忠民. 物理化学学报, 2009, 25, 1867.]
(17) Srinivas, K.; Sitha, S.; Rao, V. J.; Bhanuprakash, K. Opt. Mater. 2006, 28, 1006.
(18) Milian, B.; Orti, E.; Hernandez, V.; Navarrete, J. T. L.; Otsubo, T. J. Phys. Chem. B 2003, 107, 12175.
(19) Bo, D. S.; Ren, A. M.; Feng, J. K.; Yang, L. Chem. J. Chin. Univ. 2007, 28, 955.
[薄冬生, 任爱民, 封继康, 杨丽. 高等学校化学学报, 2007, 28, 955.]
(20) Thomas, K. R. J.; Lin, J. T.; Tao, Y. T.; Ko, C. W. J. Am. Chem. Soc. 2001, 123, 9404.
(21) Hua, J. L.; Zhang, W.; Luo, J. D.; Qin, J. G.; Sheng, Y.; Lu, Z. H. J. Chem. Res. -S 2001, 10, 418.
(22) Panthi, K.; Adhikari, R. M.; Kinstle, T. H. J. Phys. Chem. A 2010, 114, 4542.
(23) Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
(24) Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; et al. Gaussian 03, Revision C.02; Gaussian Inc.: Wallingford, CT, 2004.
(25) Kanis, D. R.; Ratner, M. A.; Marks, T. J. Chem. Rev. 1994, 94, 195.
(26) Radovic, L. R.; Karra, M.; Skokova, K.; Thrower, P. A.; Carta, G.; Cincotti, A.; Tretiak, S.; Chernyak, V.; Mukamel, S. J. Chem. Phys. Lett. 1998, 287, 75.

[1]	Xingang Fei, Haiyan Tan, Bei Cheng, Bicheng Zhu, Liuyang Zhang. 2D/2D Black Phosphorus/g-C₃N₄ S-Scheme Heterojunction Photocatalysts for CO₂ Reduction Investigated using DFT Calculations [J]. Acta Phys. -Chim. Sin., 2021, 37(6): 2010027-0.
[2]	Yunfei Wang, Jianhua Liu, Mei Yu, Jinyan Zhong, Qisen Zhou, Junming Qiu, Xiaoliang Zhang. SnO₂ Surface Halogenation to Improve Photovoltaic Performance of Perovskite Solar Cells [J]. Acta Phys. -Chim. Sin., 2021, 37(3): 2006030-0.
[3]	Xuezhu Xiao, Xiaofang Cao, Dongbo Zhao, Chunying Rong, Shubin Liu. Quantification of Molecular Basicity for Amines: a Combined Conceptual Density Functional Theory and Information-Theoretic Approach Study [J]. Acta Physico-Chimica Sinica, 2020, 36(11): 1906034-0.
[4]	Zhichao Huang,Yazhong Dai,Xiaojie Wen,Dan Liu,Yuxuan Lin,Zhen Xu,Jian Pei,Kai Wu. Conformational Switching of Verdazyl Radicals on Au(111) [J]. Acta Physico-Chimica Sinica, 2020, 36(1): 1907043-0.
[5]	Dan WANG,Xunlei DING,Henglu LIAO,Jiayu DAI. Methane Activation on (Au/Ag)₁-Doped Vanadium Oxide Clusters [J]. Acta Physico-Chimica Sinica, 2019, 35(9): 1005-1013.
[6]	Qiang CHEN,Li-Xue JIANG,Hai-Fang LI,Jiao-Jiao CHEN,Yan-Xia ZHAO,Sheng-Gui HE. Thermal Activation of Methane by Diatomic Vanadium Boride Cations [J]. Acta Physico-Chimica Sinica, 2019, 35(9): 1014-1020.
[7]	Mengru HAN,Yanan ZHOU,Xuan ZHOU,Wei CHU. Tunable Reactivity of MNi₁₂ (M = Fe, Co, Cu, Zn) Nanoparticles Supported on Graphitic Carbon Nitride in Methanation [J]. Acta Physico-Chimica Sinica, 2019, 35(8): 850-857.
[8]	Yue ZHAO,Jiatong CUI,Jichuang HU,Jiabi MA. Reactivities of VO_1–4⁺ Toward n-C_mH_2m+2 (m = 3, 5, 7) as Functions of Oxygen Content and Carbon Chain Length [J]. Acta Phys. -Chim. Sin., 2019, 35(5): 531-538.
[9]	Martínez GONZÁLEZ Marco,Carlos CÁRDENAS,Juan I. RODRÍGUEZ,Shubin LIU,Farnaz HEIDAR-ZADEH,Ramón Alain MIRANDA-QUINTANA,Paul W. AYERS. Quantitative Electrophilicity Measures [J]. Acta Phys. -Chim. Sin., 2018, 34(6): 662-674.
[10]	Paul W. AYERS,Mel LEVY. Levy Constrained Search in Fock Space: An Alternative Approach to Noninteger Electron Number [J]. Acta Phys. -Chim. Sin., 2018, 34(6): 625-630.
[11]	Tian LU,Qinxue CHEN. Revealing Molecular Electronic Structure via Analysis of Valence Electron Density [J]. Acta Phys. -Chim. Sin., 2018, 34(5): 503-513.
[12]	Farnaz HEIDAR-ZADEH,Paul W. AYERS. Generalized Hirshfeld Partitioning with Oriented and Promoted Proatoms [J]. Acta Phys. -Chim. Sin., 2018, 34(5): 514-518.
[13]	Yueqi YIN,Mengxu JIANG,Chunguang LIU. DFT Study of POM-Supported Single Atom Catalyst (M₁/POM, M = Ni, Pd, Pt, Cu, Ag, Au, POM = [PW₁₂O₄₀]^3-) for Activation of Nitrogen Molecules [J]. Acta Phys. -Chim. Sin., 2018, 34(3): 270-277.
[14]	Fanhua YIN,Kai TAN. Density Functional Theory Study on the Formation Mechanism of Isolated-Pentagon-Rule C₁₀₀(417)Cl₂₈ [J]. Acta Phys. -Chim. Sin., 2018, 34(3): 256-262.
[15]	Robert C MORRISON. Fukui Functions for the Temporary Anion Resonance States of Be^-, Mg^-, and Ca^- [J]. Acta Phys. -Chim. Sin., 2018, 34(3): 263-269.

Second-Order Nonlinear Optical Properties of Organic Heteroaromatic Molecules with Carbazole Chromophores

PDF

Like

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Metrics

Comments

Recommended 0