Exploiting Activated Alkyne Chemistry for the Synthesis of Tailored Amphiphilic Janus Dendrimers with Aggregation‐Induced Emission and Their Assemblies for Cell Imaging

Amphiphilic Janus dendrimers (AJDs) are a promising class of macromolecules capable of self-assembling into well-defined nanostructures. In this study, AJDs were synthesized employing, for the first time, the activated alkyne-hydroxyl "click" chemistry approach, enabling the construction of dendritic architectures under mild conditions. The AJDs were functionalized with a π-extended tetraphenylethylene (TPE) derivative, imparting aggregation-induced emission (AIE) property. These AJDs self-assembled into fluorescent nanostructures, including micelles and dendrimersomes, with tunable dimensions. The AIE-active assemblies demonstrated strong photoluminescence upon formation and were characterized by narrow size distributions. Cytotoxicity and cellular uptake studies using Chinese Hamster Ovary K1 (CHO-K1) cells revealed excellent biocompatibility and efficient cellular internalization, confirming their potential for live-cell imaging. Importantly, the extended π-conjugation of the TPE derivative facilitated excitation at longer wavelengths, compatible with conventional confocal microscopy. This work showcases the versatility of activated alkyne-hydroxyl "click" chemistry in dendrimer synthesis and highlights the potential of these AJD-based nanostructures in nanomedicine, particularly for imaging and diagnostic applications.