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Article Abstract

Herein we report a one-pot strategy for the synthesis and functionalization of hyperbranched polytriazoles by means of the Huisgen 1,3-dipolar cycloaddition of an AB-type monomer containing an alkyne and two azide groups. The AB monomer is synthesized starting from dimethyl 5-hydroxyisophthalate in four steps with an overall yield of 58%, and the synthesis and purification are straightforward. The synthesis of end-capped hyperbranched polytriazoles (HBPTs) can be achieved via the Huisgen cycloaddition of the AB monomer using only heat, followed by functionalization with either sulfonic acid (-SOH) or pentafluorophenyl (-Ph-F) end groups. The resulting functional hyperbranched polytriazoles, HBPT-Ph-SOH and HBPT-Ph-F, are characterized by H NMR and FT-IR spectroscopies as well as gel-permeation chromatography. The film is fabricated simply by blending the two polymers, and the ion exchange capacity and ion conductivity are measured.

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http://www.ncbi.nlm.nih.gov/pmc/articles/PMC12364098PMC
http://dx.doi.org/10.1080/15685551.2025.2547342DOI Listing

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Herein we report a one-pot strategy for the synthesis and functionalization of hyperbranched polytriazoles by means of the Huisgen 1,3-dipolar cycloaddition of an AB-type monomer containing an alkyne and two azide groups. The AB monomer is synthesized starting from dimethyl 5-hydroxyisophthalate in four steps with an overall yield of 58%, and the synthesis and purification are straightforward. The synthesis of end-capped hyperbranched polytriazoles (HBPTs) can be achieved via the Huisgen cycloaddition of the AB monomer using only heat, followed by functionalization with either sulfonic acid (-SOH) or pentafluorophenyl (-Ph-F) end groups.

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In this work, a series of polytriazole-based unimolecular nanocontainers (UNs) with good water solubility, uniformity, and colloidal stability via a bottom-up chain-growth copper-catalyzed azide-alkyne cycloaddition (co)polymerization that features tunable size, degree of branching (DB), and functionality of the UNs is developed. A broad selection of hydrophobic payload molecules, including Nile red (NR), camptothecin, pyrene, 1-pyrenemethanol, and IR676, are successfully encapsulated to demonstrate the high versatility of these polymers as UNs. Using NR as a probe guest, the relationship between the encapsulation performance and the structural properties of UNs, including size and DB, is investigated.

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This study evaluated the supramolecular properties of a new family of water-soluble hyperbranched polytriazoles that have a unimolecular micelle structure. Two new, structurally related hyperbranched polymers (HBPa and HBPn), with the same size ( = 11 nm) and core-shell architecture, were prepared and found to act as nanoscale hosts for a broad spectrum of molecular guests. The globular-shaped hyperbranched polymers were synthesized by a straightforward one-pot polymerization method that permits easy synthetic control of the multiple functional groups within the core.

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Construction of Functional Hyperbranched Poly(phenyltriazolylcarboxylate)s by Metal-Free Phenylpropiolate-Azide Polycycloaddition.

Macromol Rapid Commun

December 2018

Department of Chemistry, Hong Kong Branch of Chinese National Engineering Research Center for Tissue Restoration and Reconstruction, The Hong Kong University of Science & Technology, Clear Water Bay, Kowloon, Hong Kong, China.

The 1,3-dipolar cycloaddition of activated internal alkynes with azides has been developed into an efficient polymerization reaction for constructing functional linear 1,4,5-trisubstitued polytriazoles. However, it is rarely employed for the synthesis of hyperbranched polymers. In this work, metal-free polycycloadditions of tris(3-phenylpropiolate)s (1) and tetraphenylethene-containing diazides (2) are performed in dimethylformamide at 100 °C for 7 and 12 h, producing hyperbranched poly(phenyltriazolylcarboxylate)s (hb-PPTCs) with high molecular weights and satisfactory regioregularities in good yields.

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