Recently, various AIE-based materials with new characteristics and functions have been developing for different fields. Many chiral polymers are attracting the research interests for the new multifunctional materials in biomedicine, chiral recognition, etc. In this work, novel AIE copolymers with chirality activity were successfully fabricated for the first time. Firstly, a new fluorescent monomer (R)-THM with AIE effect and chirality activity was firstly synthesized by Suzuki reaction and enzymatic transesterification reaction. The quantum yield of (R)-THM increased to 0.643 from 0.100 of its substrate TBP with remarkable red-shift of emission spectra, which was consistent with their quantum chemical calculations of HOMO and LUMO situations, and its specific optical rotation ${[\alpha ]}_D^{25°C}$ was about −9.67°. Subsequently, a series of chiral AIE copolymers of PEG-(R)-THM1 and PEG-(R)-THM2 were prepared via RAFT polymerization of (R)-THM and PEGMA with different feeding ratios. Their molecular weights were about 2.0 × 10⁴ g/mol with narrow polydispersity index (PDI), and the kinetics analysis presented a pseudo-first-order linear procedure. For the molar 24.2%–32.3% feeding ratio of (R)-THM, the actual fraction of (R)-THM in the copolymers PEG-(R)-THM1 and PEG-(R)-THM2 was respectively about 22.3% and 30.2%, and the ${[\alpha ]}_D^{25°C}$ value of copolymers PEG-(R)-THM1 and PEG-(R)-THM2 was about −2.51° and −3.74°. The amphiphilic structure of the obtained PEG-(R)-THM make them be easily dispersed in water solution and tend to self-assemble into fluorescent organic nanoparticles (FONs) with 100–150 nm diameter by TEM, and their maximum emission wavelength presented at 495 nm with obvious AIE effect. Moreover, the PEG-(R)-THM FONs had good biological compatibility, desirable low cytotoxicity and good cells absorption effect, which showed the great potential in bioimaging application.

近来，已经针对不同领域开发了具有新特性和功能的各种基于AIE的材料。在生物医学，手性识别等方面，许多手性聚合物吸引了新型多功能材料的研究兴趣。在这项工作中，首次成功制备了具有手性活性的新型AIE共聚物。首先，通过铃木反应和酶促酯交换反应，合成了具有AIE作用和手性活性的新型荧光单体（R）-THM。（R）-THM的量子产率从其底物TBP的0.100增加到0.643，具有明显的发射光谱红移，这与它们对HOMO和LUMO态的量子化学计算及其比旋光度一致${[\alpha ]}_d^{25°C}$大约为-9.67°。随后，通过不同进料比的（R）-THM和PEGMA的RAFT聚合反应，制备了一系列PEG-（R）-THM1和PEG-（R）-THM2的手性AIE共聚物。它们的分子量约为2.0×10 ⁴  g / mol，具有窄的多分散指数（PDI），动力学分析显示为拟一级线性程序。对于（R）-THM的24.2％–32.3％摩尔进料比，在共聚物PEG-（R）-THM1和PEG-（R）-THM2中的（R）-THM实际分数分别约为22.3％和30.2％，${[\alpha ]}_d^{25°C}$共聚物PEG-（R）-THM1和PEG-（R）-THM2的值约为-2.51°和-3.74°。所得PEG-（R）-THM的两亲结构使其易于分散在水溶液中，并倾向于通过TEM自组装成直径为100-150 nm的荧光有机纳米粒子（FON），其最大发射波长为495 nm具有明显的AIE效应。此外，PEG-（THM）FONs具有良好的生物相容性，理想的低细胞毒性和良好的细胞吸收作用，显示出在生物成像应用中的巨大潜力。