Synthesis, Characterization, Spectroscopy and Theoretical Calculation of Two Novel Carbazole Derivatives
YANG Lin1,2,ZHAO Xiang-hua2,LI Zun-yun3,DENG Chong-hai1,2,SHAO Guo-quan1,WU Jie-ying2,TIAN Yu-peng2,4
1. Department of Chemistry and Materials Engineering, Hefei University, Hefei 230022, China 2. Department of Chemistry and Chemical Engineering, Anhui University, Hefei 230039, China 3. Department of Chemical Physics, University of Science and Technology of China, Hefei 230026, China 4. State Key Laboratory of Coordination Chemistry, Nanjing University, Nanjing 210093, China
Abstract：Two novel carbazole derivatives, 3-acetyl-9-n-hexylcarbazole(AHCZ) and 3,6- diacetyl-9-n-hexylcarbazole(DHCZ) were synthesized through Friedel-Crafts reaction. The compounds were characterized by IR spectra, 1H NMR, MS and elemental analysis. UV-visible spectra of AHCZ and DHCZ were measured and compared with those of their precursors, 9-hexylcarbazole(HCZ) and carbazole(CZ). DHCZ and AHCZ exhibited strong absorption band, revealing the extent of π conjugation in the system. TD-DFT method was performed to analyze the electronic absorption spectra of AHCZ and DHCZ, and the calculated excitation energies and oscillator strengths were compared with the experimental results.
Key words：3-acetyl-9-n-hexylcarbazole;3;6-diacetyl-9-n-hexylcarbazole;Electronic absorption spectra;Density functional theory
[1] Konig B, Pelka M, Zieg H, et al. J. Am. Chem. Soc., 1999, 121: 1681. [2] Boyde S, Strouse G F, Jones, et al. J. Am. Chem. Soc., 1989, 111: 7448. [3] Tamai N, Yamamaki T, Yamazaki I. J. Phys. Chem., 1987, 91:841. [4] Lippert Von E Z. Electrochem., 1957, 61: 962. [5] Baur J W, Alexander M D, Banach J M, et al. Chem. Mater., 1999, 11: 2899. [6] Demas J N, Crosby G A. J. Phys. Chem., 1971, 75: 991. [7] Ren Y, Yu X Q, Zhang D J, et al. J. Mater. Chem., 2002, 12: 3431. [8] Robinson M R, Bazan G C, ORegan M B. Chem. Comm., 2000, (17): 1645. [9] Bian Z Q, Wang K Z, Jin L P. Polyhedron, 2002, 21(3): 313. [10] Guan M, Bian Z Q, Li F Y, et al. New J. Chem., 2003, 27: 1731. [11] Huang L, Wang K Z, Huang C H, et al. J. Mater. Chem., 2001, 11: 790. [12] Jose M, Rodriguez-P, Virgil P. Macromolecules, 1986, 19: 55. [13] Yang J X, Tao X T, Yuan C X, et al. J. Am. Chem. Soc., 2005, 127: 3278. [14] DENG Chong-hai, HU Han-mei, WU Jie-ying, et al(邓崇海, 胡寒梅, 吴杰颖, 等). Chinese Journal of Synthetic Chemistry(合成化学), 2006, 14(3): 261. [15] Becke A D. J. Chem. Phys., 1993, 98: 5648. [16] Lee C, Yang W, Parrs R G. Phys. Rev. B, 1988, 37: 785. [17] Frisch M J, et al. Gaussian, Inc, Pittsburgh PA, 1998. [18] YU Qian , LUO Zong-ming, YANG Chi, et al(余 倩, 罗宗铭, 杨 迟, 等). Spectroscopy and Spectral Analysis(光谱学与光谱分析), 2004, 24(2): 162.
