磺化四苯乙烯荧光染料的合成及其发光性能

Synthesis and luminescent properties of sulfonated tetraphenylethylene fluorescent dyes

为了开发在蛋白质纤维上可应用的新型荧光染料,选用具有聚集诱导发光效应(Aggregation-induced emission,AIE)的四苯乙烯(Tetraphenylethylene,TPE)为原料,以浓硫酸和氯磺酸为磺化试剂合成了四磺化四苯乙烯(TPE-4S)和一磺化四苯乙烯(TPE-1S)荧光染料,探究其聚集诱导发光效应,并研究其对蛋白质纤维的上染性能,分析荧光染料在纤维上的发光性能。结果表明:TPE-4S和TPE-1S具有聚集诱导发光效应。两种荧光染料与酸性染料相似可上染蛋白质纤维,磺酸基的数量影响其在纤维上的最大上染量,TPE-4S在羊毛上的最大上染量可达7.0%;由于染料分子与纤维上氨基的离子键作用,使得上染纤维上的磺化四苯乙烯分子具有发光性能。与普通荧光染料相比,TPE-4S在上染量为5.0%时,发生荧光淬灭,TPE-1S在上染量为6.0%时仍然不会发生荧光淬灭。具有聚集诱导效应的荧光染料能有效克服发光材料荧光淬灭的问题。

In order to develop the new fluorescent dyes that can be applied to protein fibers,tetrasulfonated tetraphenylethylene(TPE-4S)and monosulfonated tetraphenylene(TPE-1S)fluorescent dyes with aggregation-induced emission(AIE)are synthesized from tetraphenylethylene(TPE)using concentrated sulfuric acid and chlorosulfonic acid as sulfonation reagents.Besides,the AIE was investigated,and the dyeing properties on protein fibers were also studied,while the luminescence properties of fluorescent dyes on fibers were analyzed.The results show that TPE-4S and TPE-1S have aggregation-induced emission effect.In addition,the two fluorescent dyes can dye protein fibers similar to acid dyes.The number of sulfonic acid groups affects the maximum dyeing uptake on the fibers,and the maximum dye uptake of TPE-4S on wool can reach 7.0%.Due to the ionic bond between the dye molecules and the amino groups on the fiber,the sulfonated tetrastyrene molecules on the dyed fibers have luminescent properties.Compared with ordinary fluorescent dyes,TPE-4S has fluorescence quenching when the dye uptake is 5.0%,but TPE-1S still does not have fluorescence quenching when the dye uptake is 6.0%,which provides fluorescent dyes with aggregation-induced emission effect can effectively overcome the problem of fluorescence quenching of luminescent materials.