四苯乙烯衍生物的合成及聚集诱导发光性质

Synthesis and Aggregation-Induced Emission Properties of Tetraphenylethylene Derivatives

以2,2'-联吡啶(Bpy)为母体,通过Suzuki偶联反应在其5位和5'位引入了四苯乙烯(TPE)基团,设计合成了5-四苯乙烯-2,2'-联吡啶(Bpy-1TPE)和5,5'-二四苯乙烯-2,2'-联吡啶(Bpy-2TPE)两个具有聚集诱导发光(AIE)性质的荧光分子。经1HNMR、13CNMR及EA对目标产物进行了结构测试,并考察了其紫外-可见吸收、荧光发射、AIE、压致变色性以及结构与性质之间的构效关系。结果表明:相对于具有1个四苯乙烯单元的Bpy-1TPE,含2个四苯乙烯单元的Bpy-2TPE共轭体系更大且电荷呈对称分布,能隙宽度较低,其在二氯甲烷溶液中的最大发射峰由483 nm红移至490 nm。Bpy-2TPE表现出明显的AIE性质和压致变色性质,其固体样品经研磨后最大发射波长可由485 nm红移至500 nm。

Two kinds of compounds bearing tetraphenylethylene （TPE） moiety and possessing aggregation-induced emission （ AIE ） active, 5-（ 4-（ 1,2,2-triphenylvinyl ） phenyl ） -2,2＇-bipyridine （Bpy-ITPE） and 5,5 ＇-bis （ 4-（ 1,2,2-triphenylvinyl ） phenyl ） -2,2＇-bipyridine （ Bpy-2TPE ）, were synthesized via Suzuki coupling reaction of 4- （1,2,2-triphenylvinyl） phenylboronic acid with 5-bromo- 2,2＇-bipyridine and 5,5＇-dibromo-2,2＇-bipyridine, respectively. 1HNMR and IZCNMR spectra and elemental analysis were employed to confirm the structure of the targeted products. Their UV-vis absorption, fluorescence, AIE, piezochromic properties and structure-property correlation were investigated. Compared with Bpy-1TPE, Bpy-2TPE containing two TPE units has a larger conjugation and a symmetrical charge distribution, which exhibits a lower energy gap width. A red-shift of the emission from 483 nm to 490 nm in CH2C12 was observed. Bpy-2TPE also shows obvious AIE and piezochromic properties. The maximum emission of its solid sample displayed a red-shift from 485 to 500 nm after grinding.