双枝[1,3,4]-噁二唑衍生物的合成与荧光性质

Synthesis and Fluorescence Properties of Bisbranched 1,3,4-Oxadiazole Derivatives

通过Wittig反应和Heck反应合成了三个双枝噁二唑衍生物:N-{{{3,5-二-[5-(4-叔丁基苯基)-1,3,4-噁二唑-2]-苯基}-E-乙烯基}-4-苯基}二苯胺(BBOD-2),N,N-双{{{3,5-二-[5-(4-叔丁基苯基)-1,3,4-噁二唑-2]-苯基}-E-乙烯基}-4-苯基}苯胺(BBOD-3),N,N,N-三{4-{2-{3,5-二-[5-(4-叔丁基苯基)-1,3,4-噁二唑-2]-苯基}-E-乙烯基}苯基}胺(BBOD-4).化合物结构经过红外光谱、核磁共振谱、质谱和熔点确证,测定了它们在不同溶剂中的紫外光谱和单光子荧光光谱.BBOD-1,BBOD-2,BBOD-3,BBOD-4在二氯甲烷中的最大吸收峰分别位于295,390,398和408nm;最大发射峰分别为360,486,483和487nm.讨论了Stokes位移与溶剂极性的关系.

Three novel bisbranched oxadiazole derivatives, N- { 4- { 2- { 3,5-di[5-（4-tert-butylphenyl）- 1,3,4- oxadiazol-2-yl]phenyl }-E-vinyl } phenyl }-diphenylamine （BBOD-2）, N,N-di{ 4- { 2- { 3,5-di[5-（4-tert-buty- phenyl）-1,3,4-oxadiazol-2-yl]phenyl}-E-vinyl}phenyl}aniline （BBOD-3） and N,N,N-tris{4-{2-{3,5-di[5-（4- tert-butylphenyl）- 1,3,4-oxadiazol-2-yl]phenyl } -E-vinyl } phenyl } amine （BBOD-4）, were synthesized through Wittig and Heck reactions. Their structures were characterized by IR, ^1H NMR, MS and melting points. A detailed spectrum study of these molecules, including absorption and fluorescence in different solvents, was conducted. The maximum absorption peaks in dichloromethane were at 390 nm for BBOD-2, 398 nm for BBOD-3 and 408 nm for BBOD-4, respectively. The maximum emission wavelengths were at 486 nm for BBOD-2, 483 nm for BBOD-3 and 487 nm for BBOD-4 in dichloromethane, respectively. The relationship of Stokes shift with solvent polarity was discussed.