Citation: ZHAO Min, ZHANG Yuan, WANG Lu. Second-Order Nonlinear Optical Properties of Organic Heteroaromatic Molecules with Carbazole Chromophores[J]. Acta Physico-Chimica Sinica, ;2011, 27(03): 584-588. doi: 10.3866/PKU.WHXB20110316 shu

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

1.
College of Chemistry and Chemical Engineering, Bohai University, Jinzhou 121000, Liaoning Province, P. R. China

Received Date: 7 October 2010
Available Online: 28 January 2011
Fund Project: 国家自然科学基金(20871022)资助项目 (20871022)

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 od transparency. All the compounds may have potential application in the development of NLO materials.
- Density functional theory,
- Carbazole,
- Second-order nonlinear optical property,
- Electronic spectrum
1. [1]
  
  (1) Geskin, V. M.; Lambert, C.; Bredas, J. L. J. Am. Chem. Soc. 2003, 125, 15651.
2. [2]
  (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. [3]
  (3) Humphrey, J. L.; Lott, K. M.; Wright, M. E.; Duciauskas, D. J. Phys. Chem. B 2005, 109, 21496.
4. [4]
  (4) Liu, C. G.; Qiu, Y. Q.; Su, Z. M.; Yang, G. C.; Sun, S. L. J. Phys. Chem. C 2008, 112, 7021.
5. [5]
  (5) Rao, V. P.; Jen, A. K. Y.; Wong, K. Y.; Drost, K. J. Tetrahedron Lett. 1993, 34, 1747.
6. [6]
  (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. [7]
  (7) Bai, H. T.; Lin, H. C.; Luh, T. Y. J. Org. Chem. 2010, 75, 4591.
8. [8]
  (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. [9]
  (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. [10]
  (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. [11]
  (11) Ma, J.; Li, S.; Jiang, Y. Macromolecules 2002, 35, 1109.
12. [12]
  (12) Dalton, L.; Davies, J.; Elan van, A.; Sullivan, P. J. Am. Chem. Soc. 2008, 130, 10565.
13. [13]
  (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. [14]
  (14) Qian, Y. Dyes Pigments 2008, 76, 277.
15. [15]
  (15) Albert, D. L.; Marks, T. J.; Ratner, M. A. J. Am. Chem. Soc. 1997, 119, 6575.
16. [16]
  (16) Luo, S. S.; Qiu, Y. Q.; Liu, X. D.; Liu, C. G.; Su, Z. M. Acta Phys. -Chim. Sin. 2009, 25, 1867.
17. [17]
  [罗姗姗, 仇永清, 刘晓东, 刘春光, 苏忠民. 物理化学学报, 2009, 25, 1867.]
18. [18]
  (17) Srinivas, K.; Sitha, S.; Rao, V. J.; Bhanuprakash, K. Opt. Mater. 2006, 28, 1006.
19. [19]
  (18) Milian, B.; Orti, E.; Hernandez, V.; Navarrete, J. T. L.; Otsubo, T. J. Phys. Chem. B 2003, 107, 12175.
20. [20]
  (19) Bo, D. S.; Ren, A. M.; Feng, J. K.; Yang, L. Chem. J. Chin. Univ. 2007, 28, 955.
21. [21]
  [薄冬生, 任爱民, 封继康, 杨丽. 高等学校化学学报, 2007, 28, 955.]
22. [22]
  (20) Thomas, K. R. J.; Lin, J. T.; Tao, Y. T.; Ko, C. W. J. Am. Chem. Soc. 2001, 123, 9404.
23. [23]
  (21) Hua, J. L.; Zhang, W.; Luo, J. D.; Qin, J. G.; Sheng, Y.; Lu, Z. H. J. Chem. Res. -S 2001, 10, 418.
24. [24]
  (22) Panthi, K.; Adhikari, R. M.; Kinstle, T. H. J. Phys. Chem. A 2010, 114, 4542.
25. [25]
  (23) Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
26. [26]
  (24) Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; et al. Gaussian 03, Revision C.02; Gaussian Inc.: Wallingford, CT, 2004.
27. [27]
  (25) Kanis, D. R.; Ratner, M. A.; Marks, T. J. Chem. Rev. 1994, 94, 195.
28. [28]
  (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. [1]
  Hao XU , Ruopeng LI , Peixia YANG , Anmin LIU , Jie BAI . Regulation mechanism of halogen axial coordination atoms on the oxygen reduction activity of Fe-N₄ site: A density functional theory study. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 695-701. doi: 10.11862/CJIC.20240302
2. [2]
  Kaifu Zhang , Shan Gao , Bin Yang . Application of Theoretical Calculation with Fun Practice in Raman Spectroscopy Experimental Teaching. University Chemistry, 2025, 40(3): 62-67. doi: 10.12461/PKU.DXHX202404045
3. [3]
  Jie ZHAO , Sen LIU , Qikang YIN , Xiaoqing LU , Zhaojie WANG . Theoretical calculation of selective adsorption and separation of CO₂ by alkali metal modified naphthalene/naphthalenediyne. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 515-522. doi: 10.11862/CJIC.20230385
4. [4]
  Jie ZHAO , Huili ZHANG , Xiaoqing LU , Zhaojie WANG . Theoretical calculations of CO₂ capture and separation by functional groups modified 2D covalent organic framework. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 275-283. doi: 10.11862/CJIC.20240213
5. [5]
  Meifeng Zhu , Jin Cheng , Kai Huang , Cheng Lian , Shouhong Xu , Honglai Liu . Classical Density Functional Theory for Understanding Electrochemical Interface. University Chemistry, 2025, 40(3): 148-152. doi: 10.12461/PKU.DXHX202405166
6. [6]
  Yupeng TANG , Haiying YANG , Fan JIN , Nan LI . Hydrogen storage properties of C₆S₆Li₆: A density functional theory study. Chinese Journal of Inorganic Chemistry, 2025, 41(9): 1827-1839. doi: 10.11862/CJIC.20240460
7. [7]
  Yuai Duan , Xuanyu Gan , Yao Fu , Yingjie Cao , Hongliang Han , Zhanfang Ma . Application and Innovative Design of Digital Technology in the Preparation Experiment of Cis(Trans)-Diglycine Copper Complexes. University Chemistry, 2026, 41(1): 373-381. doi: 10.12461/PKU.DXHX202504048
8. [8]
  Zhiwen HUANG , Qi LIU , Jianping LANG . W/Cu/S cluster-based supramolecular macrocycles and their third-order nonlinear optical responses. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 79-87. doi: 10.11862/CJIC.20240184
9. [9]
  Yonghui ZHOU , Rujun HUANG , Dongchao YAO , Aiwei ZHANG , Yuhang SUN , Zhujun CHEN , Baisong ZHU , Youxuan ZHENG . Synthesis and photoelectric properties of fluorescence materials with electron donor-acceptor structures based on quinoxaline and pyridinopyrazine, carbazole, and diphenylamine derivatives. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 701-712. doi: 10.11862/CJIC.20230373
10. [10]
  Xiaohang JIN , Qi LIU , Jianping LANG . Room‑temperature solid‑state synthesis, structure, and third‑order nonlinear optical properties of phosphine‑ligand‑protected silver thiolate clusters. Chinese Journal of Inorganic Chemistry, 2025, 41(8): 1505-1512. doi: 10.11862/CJIC.20250125
11. [11]
  Yujie WANG , Laobang WANG , Zheng ZHANG , Qi LIU , Jianping LANG . Construction of W/Cu/S cluster-based supramolecular compounds via alkynyl/sulfur cycloaddition and their third-order nonlinear optical properties. Chinese Journal of Inorganic Chemistry, 2025, 41(10): 2069-2077. doi: 10.11862/CJIC.20250129
12. [12]
  Shantao Zhang , TianAo Hou , Yandong Wang , Zhimin Fang , Yu Wu , Haolin Wang , Tao Chen , Shuang Chen , Wenhua Zhang , Shengzhong (Frank) Liu , Shangfeng Yang . π-Conjugation-extended dinaphthocarbazole phosphonic acid as a hole-selective layer for inverted perovskite solar cells. Acta Physico-Chimica Sinica, 2026, 42(3): 100194-0. doi: 10.1016/j.actphy.2025.100194
13. [13]
  Maitri Bhattacharjee , Rekha Boruah Smriti , R. N. Dutta Purkayastha , Waldemar Maniukiewicz , Shubhamoy Chowdhury , Debasish Maiti , Tamanna Akhtar . Synthesis, structural characterization, bio-activity, and density functional theory calculation on Cu(Ⅱ) complexes with hydrazone-based Schiff base ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1409-1422. doi: 10.11862/CJIC.20240007
14. [14]
  Weina Wang , Lixia Feng , Fengyi Liu , Wenliang Wang . Computational Chemistry Experiments in Facilitating the Study of Organic Reaction Mechanism: A Case Study of Electrophilic Addition of HCl to Asymmetric Alkenes. University Chemistry, 2025, 40(3): 206-214. doi: 10.12461/PKU.DXHX202407022
15. [15]
  Zhengkun QIN , Zicong PAN , Hui TIAN , Wanyi ZHANG , Mingxing SONG . A series of iridium(Ⅲ) complexes with fluorophenyl isoquinoline ligand and low-efficiency roll-off properties: A density functional theory study. Chinese Journal of Inorganic Chemistry, 2025, 41(6): 1235-1244. doi: 10.11862/CJIC.20240429
16. [16]
  Tongqi Ye , Yanqing Wang , Qi Wang , Huaiping Cong , Xianghua Kong , Yuewen Ye . Reform of Classical Thermodynamics Curriculum from the Perspective of Computational Chemistry. University Chemistry, 2025, 40(7): 387-392. doi: 10.12461/PKU.DXHX202409128
17. [17]
  Wei Sun , Yongjing Wang , Kun Xiang , Saishuai Bai , Haitao Wang , Jing Zou , Arramel , Jizhou Jiang . CoP Decorated on Ti₃C₂T_x MXene Nanocomposites as Robust Electrocatalyst for Hydrogen Evolution Reaction. Acta Physico-Chimica Sinica, 2024, 40(8): 2308015-0. doi: 10.3866/PKU.WHXB202308015
18. [18]
  Xiaochen Zhang , Fei Yu , Jie Ma . Cutting-Edge Applications of Multi-Angle Numerical Simulations for Capacitive Deionization. Acta Physico-Chimica Sinica, 2024, 40(11): 2311026-0. doi: 10.3866/PKU.WHXB202311026
19. [19]
  Xinwan Zhao , Yue Cao , Minjun Lei , Zhiliang Jin , Tsubaki Noritatsu . Constructing S-scheme heterojunctions by integrating covalent organic frameworks with transition metal sulfides for efficient noble-metal-free photocatalytic hydrogen evolution. Acta Physico-Chimica Sinica, 2025, 41(12): 100152-0. doi: 10.1016/j.actphy.2025.100152
20. [20]
  Haifeng ZHENG , Xingzhe GUO , Yunwei WEI , Xinfang WANG , Huimin QI , Yuting YAN , Jie ZHANG , Bingwen LI . Post-synthetic modification strategy to construct Co-MOF composites for boosting oxygen evolution reaction activity. Chinese Journal of Inorganic Chemistry, 2026, 42(1): 193-202. doi: 10.11862/CJIC.20250029

Get Citation

PDF

XML

Metrics

PDF Downloads(1080)
Abstract views(3558)
HTML views(119)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142