含咔唑和偶氮苯的乙炔衍生物的合成

摘要

A acetylene derivative containing carbazole and azobenzene groups,namely,(E) -1 -(4- (4-(3-ethyny1-9 H-carbazo1-9-yl )butoxy) phenyl) -2- (4-nitrophenyl) diazene 3 (C3o H24 N4 O3,Mr =488.53) was synthesized via Sonagashira coupling reaction and Nalkylation reaction,and its structure was characterized by IR,1H NMR,13C NMR,element analysis and single-crystal X-ray diffraction.The crystal crystallizes in monoclinic system,space group P21/c with a =9.238 (3 ),b =28.240 (8 ),c =9.783 (3 )(A),β =94.253 (3) °,V=2545.2(13)(A)3,Z=4,Dc =1.275 g/cm3,F(000) =1024,μ=0.084 mm-1,R=0.0748 and wR=0.2021 for 1750observed reflections with Ⅰ＞2σ(Ⅰ).Structural analysis showed the azobenzene group of the title compound presented a trans form with torsion angle of 178.0(4)° and two phenyl groups were connected into a rigid co-plane with dihedral angle of 7.1 (2)°.The carbazole plane in 3 had a dihedral angel about 86.2 (2) ° with phenyl group,which meaned the azobenzene rigid co-plane was nearly perpendicular to the carbazole plane.Upon excitation at 557 nm for 3,a strong orange emission with the maximum wavelength at 592 nm was observed.%采用Sonagashira偶联反应和N-烷基化反应合成了含有咔唑和偶氮苯的乙炔衍生物:3-乙炔基-9-(4-[4-(硝基)苯基偶氮苯]氧)亚丁基咔唑3.其结构通过IR,1H NMR,13C NMR,元素分析和X-射线单晶衍射法测定.标题化合物属单斜晶系,P21/c空间群；a=9.238(3),b=28.240(8),c=9.783(3)(A),β=94.253(3)°,V=2545.2( 13 )(A)3,Z=4.结构分析证实化合物中的偶氮苯基团采取反式构型,扭转角为178.0(4)°,两个苯环的二面角为7.1(2)°.咔唑平面与偶氮苯刚性面几乎垂直,所成二面角为86.2(2)°.当用557 nm波长光激发,化合物在592 nm波长处表现出强的橙光发射.