Wang Zexin, Li Renfu, Chen Li, Zhai Xin, Liu Wei, Lin Xiang, Chen Liwei, Chen Nannan, Sun Shitao, Li Zhenli, Hao Jinle, Chen Xueyuan, Lin Bin, Xie Lijun
Fujian Provincial Key Laboratory of Screening for Novel Microbial Products, Fujian Institute of Microbiology, Fuzhou, China.
Department of Medicinal Chemistry, School of Pharmaceutical Engineering, Shenyang Pharmaceutical University, Shenyang, China.
Front Chem. 2022 Jan 20;9:823519. doi: 10.3389/fchem.2021.823519. eCollection 2021.
Aggregation-induced emission (AIE) has attracted much attention in the past 2 decades. To develop novel AIE-active materials, ACQ-to-AIE transformation regioisomerization is one of the most straightforward method. However, most of the reported ACQ-to-AIE transformations are achieved by migrating bulky units. In this work, a facile conversion was realized by migrating a small pyrrolidinyl group from - to -position on the rofecoxib scaffold. As a result, a pair of new isomers named and exhibited AIE behavior and ACQ activity, respectively. Moreover, also showed solvatochromic, mechanochromic, and acidochromic properties with reversible multi-stimulus behavior. Single crystal X-ray analysis of revealed that the molecular conformation and its packing mode were responsible for the AIE emission behavior. Further investigation indicated that showed high lipid droplets staining selectivity. Taken together, the current work not only provides a new design philosophy for achieving ACQ-to-AIE conversion by migrating a small pyrrolidinyl group but also presents a promising candidate for potential applications such as in security ink, optical recording and biological applications.
聚集诱导发光（AIE）在过去二十年中备受关注。为了开发新型AIE活性材料，从聚集猝灭（ACQ）到AIE的转化区域异构化是最直接的方法之一。然而，大多数已报道的从ACQ到AIE的转化是通过迁移庞大基团实现的。在这项工作中，通过将一个小的吡咯烷基从罗非昔布支架上的一个位置迁移到另一个位置实现了一种简便的转化。结果，一对名为 和 的新异构体分别表现出AIE行为和ACQ活性。此外， 还表现出溶剂致变色、机械致变色和酸致变色特性以及可逆的多刺激行为。对 的单晶X射线分析表明，分子构象及其堆积模式是AIE发射行为的原因。进一步研究表明， 表现出高的脂滴染色选择性。综上所述，当前工作不仅为通过迁移小的吡咯烷基实现从ACQ到AIE的转化提供了一种新的设计理念，而且还为安全墨水、光学记录和生物应用等潜在应用提供了一个有前景的候选物。
