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Two in One: Use of Azide Functionality for Controlled Photo-crosslinking and Click-modification of Polymer Microspheres

Albuszis, M, Roth, Peter, Pauer, W and Moritz, H-U (2016) Two in One: Use of Azide Functionality for Controlled Photo-crosslinking and Click-modification of Polymer Microspheres Polymer Chemistry, 7 (34). pp. 5414-5425.

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Spherical, micrometer-sized, azide-functional particles were produced through dispersion copolymerization of styrene and vinylbenzyl azide (VBA, 1–100 wt-% of monomer feed) in ethanol in the presence of stabilizers. The obtained microspheres were characterized by SEM, disc centrifuge, FT-IR and NMR spectroscopy, elemental analysis, DSC, and TGA, had measured azide loadings of up to 5.58 mmol/g, and average diameters that decreased with increasing azide content from 2.8 to 0.8 μm. Microspheres were irradiated at a wavelength of 254 nm resulting in crosslinking based on azide-to-nitrene decomposition and subsequent C–H insertion and C=C addition reactions. The conversion of azide functionality was monitored by FT-IR spectroscopy, elemental analysis, and DSC and was found to roughly follow first-order kinetics with increased rates found for microspheres with lower azide contents. Photocrosslinking preserved shapes and size distributions and, above a crosslinking degree of 10%, prevented microsphere dissolution in good solvents. By controlling the irradiation time, the amount of azide consumed for photo-crosslinking could be precisely adjusted. Residual azide groups spared during the irradiation were shown to be amenable to highly efficient CuAAC click modification with a fluorescent dye, Rhodamine B propargyl ester. Given the demand for functional crosslinked microspheres and the inherent difficulties associated with common synthetic strategies in producing such materials, this methodology based on two orthogonal chemistries of the azide functionality provides simple access to well-defined microspheres with customizable degrees of crosslinking and functional group densities.

Item Type: Article
Subjects : Chemistry
Divisions : Faculty of Engineering and Physical Sciences > Chemistry
Authors :
Date : 11 August 2016
Identification Number : 10.1039/C6PY00937A
Copyright Disclaimer : This Open Access Article is licensed under a Creative Commons Attribution-Non Commercial 3.0 Unported Licence
Uncontrolled Keywords : CuAAC on microparticles, orthogonal modification, dispersion polymerization, functional microspheres, controlled photo-crosslinking, azide chemistry
Related URLs :
Depositing User : Symplectic Elements
Date Deposited : 04 Aug 2016 09:22
Last Modified : 13 Jul 2017 11:27

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