University of Surrey

Test tubes in the lab Research in the ATI Dance Research

Multicomponent isocyanide-based synthesis of reactive styrenic and (meth)acrylic monomers and their RAFT (co) polymerization

Schmidt, S, Koldevitz, M, Noy, J-M and Roth, PJ (2015) Multicomponent isocyanide-based synthesis of reactive styrenic and (meth)acrylic monomers and their RAFT (co) polymerization POLYMER CHEMISTRY, 6 (1). pp. 44-54.

[img] Text
37_2015__Schmidt-MCR1-PolymChem.pdf - Version of Record
Restricted to Repository staff only
Available under License : See the attached licence file.

Download (1MB)
[img]
Preview
Text (licence)
SRI_deposit_agreement.pdf
Available under License : See the attached licence file.

Download (33kB) | Preview

Abstract

The multicomponent Passerini reaction of aldehydes, carboxylic acids, and isocyanides is used to produce a series of novel reactive (meth)acrylic and styrenic monomers carrying pendant double bond, (trimethylsilyl protected) triple bond, diene, acetate, or pentafluorophenyl functionality. Dichloromethane and water were compared as solvents in the synthesis of 15 different monomers, with water resulting in significantly higher, up to quantitative, isolated yields with minimal purification. Characterization by 1H, 13C, and 19F NMR spectroscopy, FT-IR spectroscopy and mass spectrometry confirmed the synthesis and high purity of the functional α-acyloxycarboxamide products. The monomers are shown to be well suited for the RAFT-synthesis of well-defined homopolymers, statistical copolymers with methyl methacrylate, poly(ethylene glycol) methyl ether methacrylate, and styrene, statistical copolymers produced from two different Passerini-derived monomers, and AB diblock copolymers. SEC-measured polydispersities were generally low, ĐM ≤ 1.29, and 1H NMR spectroscopy confirmed copolymer molar compositions in good agreement with comonomer feed ratios. We expect this synthetic strategy to provide access to a wide range of novel multifunctional materials and demonstrate preliminary postpolymerization modification of a polystyrene derivative by cleavage of its pendent acetate groups and coupling of the dye Methyl Red to the resulting alcohol groups

Item Type: Article
Subjects : Chemistry
Authors :
AuthorsEmailORCID
Schmidt, SUNSPECIFIEDUNSPECIFIED
Koldevitz, MUNSPECIFIEDUNSPECIFIED
Noy, J-MUNSPECIFIEDUNSPECIFIED
Roth, PJUNSPECIFIEDUNSPECIFIED
Date : 7 January 2015
Identification Number : 10.1039/c4py01147c
Copyright Disclaimer : Copyright 2015 Royal Society of Chemistry
Uncontrolled Keywords : Science & Technology, Physical Sciences, Polymer Science, PASSERINI REACTION, WATER, CHEMISTRY, PEG
Related URLs :
Depositing User : Symplectic Elements
Date Deposited : 19 May 2016 13:25
Last Modified : 19 May 2016 13:25
URI: http://epubs.surrey.ac.uk/id/eprint/810464

Actions (login required)

View Item View Item

Downloads

Downloads per month over past year


Information about this web site

© The University of Surrey, Guildford, Surrey, GU2 7XH, United Kingdom.
+44 (0)1483 300800