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In this study, AJDs were synthesized employing, for the first time, the activated alkyne\u2010hydroxyl \u201cclick\u201d chemistry approach, enabling the construction of dendritic architectures under mild conditions. The AJDs were functionalized with a \u03c0\u2010extended tetraphenylethylene (TPE) derivative, imparting aggregation\u2010induced emission (AIE) property. These AJDs self\u2010assembled into fluorescent nanostructures, including micelles and dendrimersomes, with tunable dimensions. The AIE\u2010active assemblies demonstrated strong photoluminescence upon formation and were characterized by narrow size distributions. Cytotoxicity and cellular uptake studies using Chinese Hamster Ovary K1 (CHO\u2010K1) cells revealed excellent biocompatibility and efficient cellular internalization, confirming their potential for live\u2010cell imaging. Importantly, the extended \u03c0\u2010conjugation of the TPE derivative facilitated excitation at longer wavelengths, compatible with conventional confocal microscopy. This work showcases the versatility of activated alkyne\u2010hydroxyl \u201cclick\u201d chemistry in dendrimer synthesis and highlights the potential of these AJD\u2010based nanostructures in nanomedicine, particularly for imaging and diagnostic applications.<\/jats:p>","DOI":"10.1002\/chem.202500385","type":"journal-article","created":{"date-parts":[[2025,4,22]],"date-time":"2025-04-22T09:09:54Z","timestamp":1745312994000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":3,"title":["Exploiting Activated Alkyne Chemistry for the Synthesis of Tailored Amphiphilic Janus Dendrimers with Aggregation\u2010Induced Emission and Their Assemblies for Cell Imaging"],"prefix":"10.1002","volume":"31","author":[{"given":"Hossein","family":"Rasoulmosaedi","sequence":"first","affiliation":[{"name":"Department of Chemistry, NanoQAM and Quebec Centre for Advanced Materials (QCAM) Universit\u00e9 du Qu\u00e9bec \u00e0 Montr\u00e9al C.P. 8888, 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