Synthesis, supramolecular structures and luminescent properties of quinacridone derivatives bearing carbazole groups  

作　　者：ZHAO GuoLi FAN Yan HUO Cheng BIAN Hang SONG WeiFeng ZHANG JingYing WANG Yue 

机构地区：[1]State Key Laboratory of Supramolecular Structure and Materials, College of Chemistry, Jilin University, Changchun 130012, China

出　　处：《Chinese Science Bulletin》2009年第10期1677-1684,共8页

基　　金：Supported by the National Natural Science Foundation of China (Grant Nos. 50773027 and 5073302);National High Technology Research and Development Program of China (Grant No. 2006AA03A162)

摘　　要：The syntheses of three carbazyl-containing quinacridone derivatives, N,N’-di((N-carbazyl)-n-butyl) quinacridone (DCBQA), N,N’-di((N-carbazyl)-n-hexyl)quinacridone (DCHQA) and N,N’-di((N-carbazyl)-n-octyl)quinacridone (DCOQA), are reported, and the photoluminescent (PL) characteristics are pre- sented. The single crystal X-ray structures of DCBQA, DCHQA and DCOQA are investigated. The crystal of DCBQA is characterized by intermolecular π…π interactions between quinacridone cores and carbazole moieties resulting in the formation of DCBQA molecule layer, in which every quinacridone core is surrounded by four carbazole groups. In DCHQA crystal, molecules assemble into two kinds of oriented columns based on intermolecular π…π interactions between quinacridone cores. The DCOQA crystal displays intermolecular CH…π and hydrogen bonding interactions feature. In DCOQA solid, every quinacridone core is sandwiched by two alkyl chains from two adjacent DCOQA molecules and simultaneously linked together with two other quinacridone cores by hydrogen bonding interactions. The PL spectra of the three compounds in solution exhibit concentration-dependent properties and their PL quantum causes decrease with the increasing concentration.The syntheses of three carbazyl-containing quinacridone derivatives, N,N＇-di（（N-carbazyl）-n-butyl） quinacridone （DCBQA）, N,N＇-di（（N-carbazyl）-n-hexyl）quinacridone （DCHQA） and N,N＇-di（（N-carbazyl）-n-octyl）quinacridone （DCOQA）, are reported, and the photoluminescent （PL） characteristics are presented. The single crystal X-ray structures of DCBQA, DCHQA and DCOQA are investigated. The crystal of DCBQA is characterized by intermolecular TT TT interactions between quinacridone cores and carbazole moieties resulting in the formation of DCBQA molecule layer, in which every quinacridone core is surrounded by four carbazole groups. In DCHQA crystal, molecules assemble into two kinds of oriented columns based on intermolecular TT TT interactions between quinacridone cores. The DCOQA crystal displays intermolecular CH TT and hydrogen bonding interactions feature. In DCOQA solid, every quinacridone core is sandwiched by two alkyl chains from two adjacent DCOQA molecules and simultaneously linked together,with two other quinacridone cores by hydrogen bonding interactions. The PL spectra of the three compounds in solution exhibit concentration-dependent properties and their PL quantum causes decrease with the increasing concentration.

关 键 词：吖啶酮衍生物 超分子结构 发光性能 合成 咔唑 氢键相互作用 喹吖啶酮 浓度依赖性 

分 类 号：TQ253.26[化学工程—有机化工] S562.01[农业科学—作物学]