Table of Contents
Journal of Polymers
Volume 2017 (2017), Article ID 6938475, 10 pages
https://doi.org/10.1155/2017/6938475
Research Article

Isolation and Characterization of 1,3-Bis(vinylbenzyl)thymine: Copolymerization with Vinylbenzyl Thymine Ammonium Chloride

1Simmons College, Department of Chemistry, 300 The Fenway, Boston, MA 02215, USA
2Warner Babcock Institute for Green Chemistry, 100 Research Dr., Wilmington, MA 01887, USA

Correspondence should be addressed to Debora M. Martino and Nancy Lee

Received 10 September 2016; Accepted 22 November 2016; Published 4 January 2017

Academic Editor: Dirk Kuckling

Copyright © 2017 Ngoc Chau H. Vy et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Abstract

A novel bioinspired molecule, 1,3-bis(vinylbenzyl)thymine (bisVBT), was isolated as a by-product during the synthesis of 1-(4-vinylbenzyl)thymine (VBT) and analyzed with various techniques: NMR, IR, and Single-Crystal X-ray Diffraction. In addition to embodying all the desired characteristics of VBT (i.e., having the ability to undergo a photodimerization reaction upon UV irradiation, a derivatization site, hydrogen bonding sites, and aromatic stacking ability) the bisVBT monomer has the added benefit of having two vinyl groups for cross-polymerization. Copolymerizing the bisVBT monomer with the charged monomer vinylbenzyl triethylammonium (VBA) chloride, different copolymers/terpolymers/cross-linked network were obtained, as it was shown by the absence of the vinyl resonance in the NMR spectra. Thermal Gravimetric Analysis (TGA) and Differential Scanning Calorimetry (DSC) showed an indication of materials with low degree of cross-linking. A Gel Permeation Chromatography (GPC) method was improved to better characterize the molecular weight distributions of the cationic structures. Preliminary qualitative cross-linking studies were performed on bisVBT-VBA copolymers, and a comparison with VBT-VBA copolymers is presented.