New AIE Emitters from the Unexpected Boron Tribromide/Boron Trichloride-mediated Cyclization Reaction and Application for Fluorescence Imaging of Lipid Droplets

IF 13.7 Q1 CHEMISTRY, MULTIDISCIPLINARY

Aggregate (Hoboken, N.J.) Pub Date : 2025-01-22 DOI:10.1002/agt2.735

Yichen Hu, Xin Gao, Junlong Ma, Zhichun Shangguan, Liangliang Chen, Guanxin Zhang, Xi-Sha Zhang, Cheng Li, Yanbang Li, Deqing Zhang

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Abstract

The aberrant behavior of lipid droplets (LDs) is often indicative of cellular dysfunction, which may contribute to the development of a range of diseases, particularly metabolic dysfunction-associated steatotic liver disease (MASLD) and atherosclerosis (AS). Consequently, there is an urgent need to develop fluorescence probes targeting LDs to monitor the progression of disease. In this study, an unanticipated one-pot boron tribromide (BBr₃)/boron trichloride (BCl₃)-promoted cyclization reaction was discovered, yielding a bromo-/chloro-substituted triphenylamine (TPA) derivative (TPA-Br/TPA-Cl). TPA-Br was successfully transformed into new TPA-containing donor-acceptor (D–A) molecules which show typical aggregation induced emission (AIE) property. Among these new AIE emitters, TPA-N shows the most promising LDs targeting specificity, lowest toxicity and best photo-stability. Ex vivo studies further demonstrate that TPA-N can be used to fluorescence image fatty liver and AS plaque quickly and effectively.

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意想不到的三溴化硼/三氯化硼介导环化反应的新型AIE发射体及其在脂滴荧光成像中的应用

脂滴（ld）的异常行为通常表明细胞功能障碍，这可能导致一系列疾病的发展，特别是代谢功能障碍相关的脂肪变性肝病（MASLD）和动脉粥样硬化（AS）。因此，迫切需要开发针对ld的荧光探针来监测疾病的进展。在这项研究中，发现了一个意想不到的一锅三溴化硼（BBr₃）/三氯化硼（BCl₃）促进的环化反应，生成了一个溴/氯取代三苯胺（TPA）衍生物（TPA- br /TPA- cl）。TPA-Br成功转化为新的含tpa的供体-受体（D-A）分子，具有典型的聚集诱导发射（AIE）性质。在这些新的AIE发射体中，TPA-N表现出最有希望的ld靶向特异性、最低的毒性和光稳定性。离体研究进一步证明TPA-N可以快速有效地对脂肪肝和AS斑块进行荧光成像。

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