两种新颖的咔唑乙酰化衍生物的合成、表征、光谱性质与量子化学研究  

Synthesis,Characterization,Spectroscopy and Theoretical Calculation of Two Novel Carbazole Derivatives

作　　者：杨林[1] 赵祥华[2] 李遵云[3] 邓崇海[1] 邵国泉[1] 吴杰颖[2] 田玉鹏[2] 

机构地区：[1]合肥学院化学与材料工程系,安徽合肥230022 [2]安徽大学化学化工学院,安徽合肥230039 [3]中国科学技术大学化学物理系,安徽合肥230026

出　　处：《光谱学与光谱分析》2008年第4期883-886,共4页Spectroscopy and Spectral Analysis

基　　金：安徽省高校青年教师科研计划项目(2005jq1228);安徽省教育厅自然科学基金项目(2006KJ159B);合肥学院科研发展基金(07KY003ZR)资助

摘　　要：采用Friedel-Crafts亲电取代反应,合成了两种新颖的咔唑乙酰化衍生物[9-己基-3-乙酰基咔唑(3-acetyl-9-n-hexylcarbazole)(AHCZ)和9-己基-3,6-二乙酰基咔唑(3,6-diacetyl-9-n-hexylcarbazole)(DHCZ)]。通过元素分析、红外光谱、核磁共振谱、有机质谱等方法进行了结构表征。测定了这两种衍生物的紫外-可见光谱,并与咔唑(CZ)及9-己基咔唑(HCZ)进行了比较。AHCZ和DHCZ的吸收强度比CZ和HCZ有明显增强,归因于AHCZ和DHCZ具有大的π共轭体系。采用密度泛函理论(density functional theory,DFT),在B3LYP/6-31G*水平上对两种化合物基态结构进行优化,用含时密度泛函理论(TDDFT)在相同水平上计算了AHCZ和DHCZ的电子吸收光谱,并比较了理论计算结果与实验值。Two novel earbazole 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, 1 H NMR, MS and elemental analysis. UV-visible spectra of AHCZ and DHCZ were measured and compared with those of their precursors, 9-hexylearbazole（HCZ） and earbazole（CZ）. DHCZ and AHCZ exhibited strong absorption band, revealing the extent of 7r 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.

关 键 词：9-己基-3-乙酰基咔唑 9-己基-3 6-二乙酰基咔唑 电子吸收光谱 密度泛函理论 

分 类 号：O614.3[理学—无机化学]