Citation: WANG Kun-Peng, WANG Chang-Sheng. Effect of Substituents on the Optical Properties of 3(5)-(9-Anthryl) Pyrazole[J]. Acta Physico-Chimica Sinica, ;2011, 27(03): 589-594. doi: 10.3866/PKU.WHXB20110303 shu

Effect of Substituents on the Optical Properties of 3(5)-(9-Anthryl) Pyrazole

1.
School of Chemistry and Chemical Engineering, Liaoning Normal University, Dalian 116029, Liaoning Province, P. R. China

Received Date: 29 October 2010
Available Online: 18 January 2011
Fund Project: 国家自然科学基金(20973088) (20973088)辽宁省高校创新团队基金(2007T091, 2008T106)资助项目 (2007T091, 2008T106)

The ground state (S₀) structures of 3(5)-(9-anthryl) pyrazole and its derivatives were obtained using the density functional theory (DFT) B3LYP/6-31G(d) method. The first singlet excited state (S₁) structures were optimized using the singlet-excitation configuration interaction (CIS)/6-31G(d) method. The absorption and emission spectra were then evaluated using the time-dependent density functional theory (TD-DFT) B3LYP method with the 6-311++G(d,p) basis set. Our calculation results reveal that for all the derivatives (electron-withdrawing groups or electron-donating groups) the calculated absorption and fluorescence emission wavelength values all show red shifts compared with the parent 3(5)-(9-anthryl) pyrazole. We also find that compared with the parent 3(5)-(9-anthryl) pyrazole, the derivatives with ―R=―BH₂, ―CCl₃, ―CHO, ―NH₂ are od candidates for longer absorption wavelength materials and for longer fluorescence emission wavelength materials.
- Absorption spectrum,
- Fluorescence emission spectrum,
- 3(5)-(9-Anthryl) pyrazole,
- Excited state
1. [1]
  
  (1) Mizukami, S.; Houjou, H.; Sugaya, K.; Koyama, E.; Tokuhisa, H.; Sasaki, T.; Kanesato, M. Chem. Mater. 2005, 17, 50.
2. [2]
  (2) Bader, M. M.; Custelcean, R.; Ward, M. D. Chem. Mater. 2003, 15, 616.
3. [3]
  (3) Wakamiya, A.; Ide, T.; Yamaguchi, S. J. Am. Chem. Soc. 2005, 127, 14859.
4. [4]
  (4) Murata, H.; Kafafi, Z. H.; Uchida, M. Appl. Phys. Lett. 2002, 80, 189.
5. [5]
  (5) Chen, J.; Law, C. C. W.; Lam, J. W. Y.; Dong, Y.; Lo, S. M. F.; Williams, I. D.; Zhu, D.; Tang, B. Z. Chem. Mater. 2003, 15, 1535.
6. [6]
  (6) Sapochak, L. S.; Benincasa, F. E.; Schofield, R. S.; Baker, J. L.; Riccio, K. K. C.; Fogarty, D.; Kohlmann, H.; Ferris, K. F.; Burrows, P. E. J. Am. Chem. Soc. 2002, 124, 6119.
7. [7]
  (7) Brinkmann, M.; Gadret, G.; Muccini, M.; Taliani, C.; Masciocchi, N.; Sironi. A. J. Am. Chem. Soc. 2000, 122, 5147.
8. [8]
  (8) Halls, M. D.; Schlegel, H. B. Chem. Mater. 2001, 13, 2632.
9. [9]
  (9) Geng, W. T.; Oda, M.; Nara, J.; Kondo, H.; Ohno, T. J. Phys. Chem. B 2008, 112, 2795.
10. [10]
  (10) Shi, L.; Hong, B.; Guan, W.; Wu, Z.; Su, Z. J. Phys. Chem. A 2010, 114, 6559.
11. [11]
  (11) Hu, B.; Gahungu, G.; Zhang, J. J. Phys. Chem. A 2007, 111, 4965.
12. [12]
  (12) Sun, M.; Niu, B.; Zhang, J. Theor. Chem. Acc. 2008, 119, 489.
13. [13]
  (13) Fan, Y.; Zhao, Y.; Ye, L.; Li, B.; Yang, G.; Wang, Y. Crystal Growth & Design 2009, 9, 1421.
14. [14]
  (14) Fan, Y.; Song, W.; Yu, D.; Ye, K.; Zhang, J.; Wang, Y. CrystEngComm 2009, 11, 1716.
15. [15]
  (15) Gaal, M.; Gadermaier, C.; Plank, H.; Moderegger, E.; Pogantsch,A.; Leising, G.; List, E. J. W. Adv. Mater. 2003, 15, 1165.
16. [16]
  (16) Zhao, Y.; Gao, H.; Fan, Y.; Zhuo, T.; Su, Z.; Liu, Y.; Wang, Y. Adv. Mater. 2009, 21, 3165.
17. [17]
  (17) Gustafsson, G.; Cao, Y.; Treacy, G. M.; Klavetter, F.; Colaneri, N.; Heeger, A. J. Nature 1992, 357, 477.
18. [18]
  (18) Chen, Y.; Au, J.; Kazlas, P.; Ritenour, A.; Gates, H.; McCreary, M. Nature 2003, 423, 136.
19. [19]
  (19) Rakow, N. A; Suslick, K. S. Nature 2000, 406, 710.
20. [20]
  (20) Zhang, H.; Zhang, Z.; Ye, K.; Zhang, J.; Wang, Y. Adv. Mater. 2006, 18, 2369.
21. [21]
  (21) Gao, L.; Lu, N.; Hao, J.; Hu, W.; Wang, W.; Wu, Y.; Wang, Y.; Chi, L. Langmuir 2008, 24, 12745.
22. [22]
  (22) Gao, L.; Lu, N.; Hao, J.; Hu, W.; Shi, G.; Wang, Y.; Chi, L. Langmuir 2009, 25, 3894.
23. [23]
  (23) Stephens, P. J.; Devlin, F. J.; Chabalowski, C. F.; Frisch, M. J. J. Phys. Chem. 1994, 98, 11623.
24. [24]
  (24) Foresman, J. B.; Head- rdon, M.; Pople, J. A.; Frisch, M. J. J. Phys. Chem. 1992, 96, 135.
25. [25]
  (25) Cancès, E.; Mennucci, B.; Tomasi, J. J. Chem. Phys. 1997, 107, 3032.
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沈阳化工大学材料科学与工程学院沈阳 110142