Self-assembly of fluorescent functional materials has attracted increasing interest in the fabrication of optoelectronic and biological nanodevices. Tetraphenylethene (TPE) is a typical dye molecule with aggregation-induced-emission (AIE) characteristics. Melding TPE carrying triple-bond functionality with diazide-containing biphenyl through “click” chemistry generates AIE-active luminogens [1,1′-biphenyl]-4,4′-diyl bis(6-(4-(4-(1,2,2-triphenylvinyl)phenyl)-1H-1,2,3-triazol-1-yl) hexanoate) [1(5)] and [1,1′-biphenyl]-4,4′-diyl bis(11-(4-(4-(1,2,2-triphenylvinyl)phenyl)-1H-1,2,3-triazol-1-yl) undecanoate) [1(10)] with solid state efficiencies up to unity. Slow addition of dilute THF solutions of 1(m) (m = 5, 10) into nonsolvents such as n-hexane and water yields self-assembled white wooly solids. TEM and SEM observations reveal the (helical) nanofibrous structure of the aggregates. Upon cooling from their concentrated hot solutions, 1(m) readily precipitate. Meanwhile, they can also form gels at high concentrations. Both precipitates and gels of 1(m) exhibit structures similar to those of the aggregates formed in nonsolvents. These results indicate that 1(m) can facilely self-assemble into high emission efficiency (helical) nanofibers, thus paving the way for their optoelectronic and biological applications.
荧光功能材料的自组装在光电和
生物纳米器件的制造中引起了越来越多的关注。四苯基
乙烯(TPE)是一种典型的
染料分子,具有聚集诱导发射(AIE)特性。通过 "点击 "
化学反应,将具有三键功能的 TPE 与含有重
氮化物的
联苯结合在一起,产生了具有 AIE 活性的发光体 [1,1′-
联苯]-4,4′-二基双(6-(4-(4-(1,2,2-三苯基
乙烯基)苯基)-1H-1、1(5)]和[1,1′-
联苯]-4,4′-二基双(11-(4-(4-(1,2,2-三苯基
乙烯基)苯基)-
1H-1,2,3-三唑-1-基)
十一烷酸酯)[1(10)],固态效率可达一倍。将 1(m)(m = 5,10)的稀 THF 溶液缓慢加入
正己烷和
水等非溶剂中,会产生自组装的白色毛状固体。
TEM 和
SEM 观察结果表明,聚集体具有(螺旋状)纳米纤维结构。从浓热溶液中冷却后,1(m) 很容易沉淀。同时,它们也能在高浓度下形成凝胶。1(m) 的沉淀物和凝胶都表现出与在非溶剂中形成的聚集体相似的结构。这些结果表明,1(m) 可以很容易地自组装成高发射效率(螺旋状)纳米纤维,从而为其光电和
生物应用铺平了道路。