Issue 31, 2015

Functional, sub-100 nm polymer nanoparticles via thiol–ene miniemulsion photopolymerization

Abstract

In this work, sub-100 nm crosslinked polythioether nanoparticles were synthesized via thiol–ene photopolymerization in miniemulsion using high-energy homogenization. The effects of the miniemulsion formulation and homogenization parameters – including inhibitor concentration, surfactant concentration, organic weight fraction, ultrasonication time and amplitude – on nanoparticle size and size distribution were investigated. Thiol–ene nanoparticles with a mean particle diameter of 46 nm were obtained under optimized conditions for the current system at 2.5 wt% organic fraction and 20 mM surfactant concentration. In an effort to demonstrate potential utility of thiol–ene nanoparticles, we exploit the step-growth radical mechanism of thiol–ene photopolymerization under non-stoichiometric conditions to fabricate functional nanoparticles that express excess thiol or alkene at the particle surface. We show that these excess functional groups can be utilized as reactive handles in thiol-Michael and radical-mediated thiol–ene reactions for immobilization of fluorescent moieties via postpolymerization modification.

Graphical abstract: Functional, sub-100 nm polymer nanoparticles via thiol–ene miniemulsion photopolymerization

Supplementary files

Article information

Article type
Paper
Submitted
24 Oct 2014
Accepted
20 Nov 2014
First published
21 Nov 2014

Polym. Chem., 2015,6, 5625-5632

Functional, sub-100 nm polymer nanoparticles via thiol–ene miniemulsion photopolymerization

D. V. Amato, D. N. Amato, A. S. Flynt and D. L. Patton, Polym. Chem., 2015, 6, 5625 DOI: 10.1039/C4PY01449A

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