Practical synthesis of water-soluble organic nanoparticles with a single reactive group and a functional carrier scaffoldElectronic supplementary information (ESI) available: Experimental details, including synthesis and characterisation of monomers and polymers, are available in the ESI. See DOI: 10.1039/c4sc00700j

• Main Authors: Bai, Yugang, Xing, Hang, Vincil, Gretchen A, Lee, Jennifer, Henderson, Essence J, Lu, Yi, Lemcoff, N. Gabriel, Zimmerman, Steven C
• Format: Article
• Language: English
• ISSN: 2041-6520; 2041-6539
• DOI: 10.1039/c4sc00700j

A new approach to prepare functional organic nanoparticles (ONPs) from linear polymers is described. The nanoparticles are obtained by ring-opening metathesis polymerisation (ROMP) of functionalised norbornene dicarboximides, side-chain amidation with tri- O -allyl-TRIS, and ring-closing metathesis (RCM). The synthesis is quite flexible and mild, allowing preparation of organic- and aqueous-soluble particles with narrow molecular weight (MW) distributions that are tunable, ranging from MW 10 to >100 kD with diameters between ca. 5 and 50 nm. The use of functional monomer(s) and/or chain-transfer agents (CTAs) leads to the fully controlled synthesis of nanoparticles containing single or multiple reactive functional groups. This non-toxic ONP scaffold can be readily used as a protective carrier for a broad range of groups using the appropriate monomers, such as a fluorescein-functionalised monomer that affords fluorescent ONPs with significantly enhanced photostability. A practical synthesis of biocompatible organic nanoparticles with a reactive group and a functional carrier scaffold was developed.