State Key Laboratory of Supramolecular Structure and Materials, College of Chemistry, Jilin University, Changchun 130012, PR China.
Langmuir. 2010 May 4;26(9):6838-44. doi: 10.1021/la904727t.
Three functionalized 9,10-distyrylanthracene (DSA) derivatives, namely, 9,10-bis(4-hydroxystyryl)anthracene (2), 9,10-bis{4-[2-(diethylamino)ethoxy]styryl}anthracene (4), and 9,10-bis{4-[2-(N,N,N-triethylammonium)ethoxy]styryl}anthracene dibromide (5), were synthesized and their fluorescence properties were investigated. The three DSA derivatives possess a typical aggregation-induced emission (AIE) property (i.e., they are nonluminescent in dilute solutions but are efficiently fluorescent as induced by molecular aggregation). Different AIE properties were tuned through molecular structure control. Dye 2 is a phenol-moiety-containing compound, which shows aggregation at pH values smaller than 10, resulting in a high fluorescence intensity. Thus, dye 2 has a pK(a) of 9.94. 4 is an amine-containing compound that starts to aggregate at slightly basic conditions, resulting in a pK(a) of 6.90. Dye 5 is an ammonium-salt-containing compound. Because it is very soluble in water, this compound has no AIE phenomenon but can interact strongly with protein or DNA to amplify its emission. Therefore, 5 is a fluorescent turn "on" biological probe for protein and DNA detection and it is also selective, which works for native BSA and ct DNA but not their denatured forms. Therefore, we not only developed a few new compounds showing the AIE phenomena but also controlled the AIE through environmental stimulation and demonstrated that the new AIE molecules are suitable for pH and biomacromolecule sensing.
三种功能化的 9,10-二芳基蒽（DSA）衍生物，即 9,10-双（4-羟苯乙烯基）蒽（2）、9,10-双{4-[2-（二乙氨基）乙氧基]苯乙烯基}蒽（4）和 9,10-双{4-[2-（N,N,N-三乙铵）乙氧基]苯乙烯基}蒽二溴化物（5），被合成并研究了它们的荧光性质。这三种 DSA 衍生物具有典型的聚集诱导发光（AIE）性质（即，它们在稀溶液中是非发光的，但在分子聚集诱导下则具有高效荧光）。通过分子结构控制，调节了不同的 AIE 性质。染料 2 是一种含有酚部分的化合物，在 pH 值小于 10 时会发生聚集，导致荧光强度很高。因此，染料 2 的 pK(a)为 9.94。4 是一种含有胺部分的化合物，在略碱性条件下开始聚集，导致 pK(a)为 6.90。染料 5 是一种含有铵盐的化合物。由于它在水中非常溶解，因此该化合物没有 AIE 现象，但可以与蛋白质或 DNA 强烈相互作用，从而增强其发射。因此，5 是一种荧光“开启”的蛋白质和 DNA 检测生物探针，它具有选择性，可用于天然 BSA 和 ctDNA 的检测，但不能用于其变性形式的检测。因此，我们不仅开发了几种显示 AIE 现象的新化合物，还通过环境刺激来控制 AIE，并证明了新的 AIE 分子适用于 pH 值和生物大分子的检测。
