Wang Jia, Zhao Yunfeng, Dou Chuandong, Sun Hui, Xu Peng, Ye Kaiqi, Zhang Jingying, Jiang Shimei, Li Fei, Wang Yue
Key Laboratory for Supramolecular Structure and Materials of Ministry of Education, College of Chemistry, Jilin University, Changchun 130012, People's Republic of China.
J Phys Chem B. 2007 May 17;111(19):5082-9. doi: 10.1021/jp068646m. Epub 2007 Apr 18.
The synthesis of two alkyl substituted quinacridone derivatives, N,N'-di(n-hexyl)-1,3,8,10-tetramethylquinacridone (1) and N,N'-di(n-hexyl)-2,9-di(t-butyl)quinacridone (2), and four dendritic quinacridone derivatives, N,N'-didendritic-1,3,8,10-tetramethylquinacridones (3-G1 and 3-G2) and N,N'-didendritic-2,9-di(tert-butyl)quinacridones (4-G1 and 4-G2) are reported. X-ray crystal structure and thermal analysis revealed that the quinacridone derivatives reported in this paper exhibit the evolution from crystalline phase to amorphous phase upon varying from alkyl substituted quinacridones to dendritic quinacridones. The concentration-dependent 1H NMR, UV-vis, and photoluminescence (PL) spectroscopic studies demonstrated the aggregation properties of the quinacridone derivatives in solution. For dendritic quinacridones with the sufficient shield of dendrons, the fluorescence concentration quenching can be significantly suppressed and emission intensity in concentrated solution and solid state could be greatly enhanced. Compound 4-G2 displays good solution process property and higher PL yield in concentrated solution, suggesting that it is a potential candidate for the fabrication of high-performance organic electroluminescent devices (OLEDs) on the basis of low-cost solution process technique.
报道了两种烷基取代喹吖啶酮衍生物，即N,N'-二（正己基）-1,3,8,10-四甲基喹吖啶酮（1）和N,N'-二（正己基）-2,9-二（叔丁基）喹吖啶酮（2），以及四种树枝状喹吖啶酮衍生物，即N,N'-二树枝状-1,3,8,10-四甲基喹吖啶酮（3-G1和3-G2）和N,N'-二树枝状-2,9-二（叔丁基）喹吖啶酮（4-G1和4-G2）的合成。X射线晶体结构和热分析表明，本文报道的喹吖啶酮衍生物在从烷基取代喹吖啶酮变为树枝状喹吖啶酮时呈现出从晶相到非晶相的演变。浓度依赖性的1H NMR、紫外可见光谱和光致发光（PL）光谱研究证明了喹吖啶酮衍生物在溶液中的聚集性质。对于具有足够树枝体屏蔽的树枝状喹吖啶酮，荧光浓度猝灭可得到显著抑制，浓溶液和固态下的发射强度可大大增强。化合物4-G2在浓溶液中显示出良好的溶液加工性能和较高的PL产率，表明它是基于低成本溶液加工技术制造高性能有机电致发光器件（OLED）的潜在候选物。
