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.

Linked References

  1. J.-F. Lutz, A. F. Thünemann, and R. Nehring, “Preparation by controlled radical polymerization and self-assembly via base-recognition of synthetic polymers bearing complementary nucleobases,” Journal of Polymer Science, Part A: Polymer Chemistry, vol. 43, no. 20, pp. 4805–4818, 2005. View at Publisher · View at Google Scholar · View at Scopus
  2. Y. Imai, T. Ogoshi, K. Naka, and Y. Chujo, “Formation of IPN organic-inorganic polymer hybrids utilizing the photodimerization of thymine,” Polymer Bulletin, vol. 45, no. 1, pp. 9–16, 2000. View at Publisher · View at Google Scholar · View at Scopus
  3. Y. Dahman, J. E. Puskas, A. Margaritis, Z. Merali, and M. Cunningham, “Novel thymine-functionalized polystyrenes for applications in biotechnology. Polymer synthesis and characterization,” Macromolecules, vol. 36, no. 7, pp. 2198–2205, 2003. View at Publisher · View at Google Scholar · View at Scopus
  4. H. Xu, R. Hong, T. Lu, O. Uzun, and V. M. Rotello, “Recognition-directed orthogonal self-assembly of polymers and nanoparticles on patterned surfaces,” Journal of the American Chemical Society, vol. 128, no. 10, pp. 3162–3163, 2006. View at Publisher · View at Google Scholar · View at Scopus
  5. C. M. Cheng, M. I. Egbe, J. M. Grasshoff et al., “Synthesis of 1-(vinylbenzyl)thymine, a novel, versatile multi-functional monomer,” Journal of Polymer Science Part A: Polymer Chemistry, vol. 33, no. 14, pp. 2515–2519, 1995. View at Publisher · View at Google Scholar
  6. X. Yang, P. Xu, S. Ding, M. Radosz, and Y. Shen, “Synthesis of 1-(4-vinylbenzyl)thymine and its polymerization by RAFT and ATRP techniques,” Polymer Preprints, vol. 45, no. 1, pp. 1061–1062, 2004. View at Google Scholar
  7. C. Kiarie, J. Bianchini, S. Trakhtenberg, and J. C. Warner, “Methylene blue adsorption on thymine based polyvinylphenylsulfonate films,” Journal of Macromolecular Science, Part A: Pure and Applied Chemistry, vol. 42, no. 11, pp. 1489–1496, 2005. View at Publisher · View at Google Scholar · View at Scopus
  8. A. L. Barbarini, D. A. Estenoz, and D. M. Martino, “Synthesis, characterization and curing of bioinspired polymers based on vinyl benzyl thymine and triethyl ammonium chloride,” Macromolecular Reaction Engineering, vol. 4, no. 6-7, pp. 453–459, 2010. View at Publisher · View at Google Scholar · View at Scopus
  9. D. M. Martino, D. Reyna, D. A. Estenoz, S. Trakhtenberg, and J. C. Warner, “Photosensitization of bioinspired thymine-containing polymers,” Journal of Physical Chemistry A, vol. 112, no. 21, pp. 4786–4792, 2008. View at Publisher · View at Google Scholar · View at Scopus
  10. A. L. Barbarini, D. L. Reyna, and D. M. Martino, “The effect of light intensity, film thickness, and monomer composition in styrene-based bioinspired polymers,” Green Chemistry Letters and Reviews, vol. 3, no. 3, pp. 231–237, 2010. View at Publisher · View at Google Scholar · View at Scopus
  11. J. M. Grasshoff, L. D. Taylor, and J. C. Warner, U.S. Patent 5,455,349, October 1995.
  12. J. M. Grasshoff, L. D. Taylor, and J. C. Warner, “Method of imaging using a polymeric photoresist having pendant vinylbenzyl thymine groups,” US Patent 5,616,451, April 1997.
  13. J. M. Grasshoff, L. D. Taylor, and J. C. Warner, US Patent 5,708,106, January 1998.
  14. J. C. Warner, A. S. Cannon, J. Raudys, and A. Undurti, PCT International Application WO 2004058187, December 2004.
  15. Y. Inaki, “Thymine polymers as high resolution photoresists and reversiblephoto-recording materials,” Polymer News, vol. 17, pp. 367–371, 1992. View at Google Scholar
  16. S. Trakhtenberg, J. C. Warner, R. Nagarajan, F. F. Bruno, L. A. Samuelson, and J. Kumar, “Spectroscopic and microscopic analysis of photo-cross-linked vinylbenzylthymine copolymers for photoresist applications,” Chemistry of Materials, vol. 18, no. 12, pp. 2873–2878, 2006. View at Publisher · View at Google Scholar · View at Scopus
  17. R. F. El-Hayek, K. Dye, and J. C. Warner, “Bacteriostatic polymer film immobilization,” Journal of Biomedical Materials Research Part A, vol. 79, no. 4, pp. 874–881, 2006. View at Publisher · View at Google Scholar · View at Scopus
  18. A. L. Barbarini, D. A. Estenoz, and D. M. Martino, “Crosslinkable micelles from diblock amphiphilic copolymers based on vinylbenzyl thymine and vinylbenzyl triethylammonium chloride,” Journal of Applied Polymer Science, vol. 132, no. 19, Article ID 41947, 2015. View at Publisher · View at Google Scholar
  19. K. Saito and J. C. Warner, “Core-shell thymine containing polymeric micelle system: study of controlled release of riboflavin,” Green Chemistry Letters and Reviews, vol. 2, no. 2, pp. 71–76, 2009. View at Publisher · View at Google Scholar
  20. G. Kaur, S. L. Y. Chang, T. D. M. Bell, M. T. W. Hearn, and K. Saito, “Bioinspired core-crosslinked micelles from thymine-functionalized amphiphilic block copolymers: Hydrogen Bonding and Photo-crosslinking Study,” Journal of Polymer Science, Part A: Polymer Chemistry, vol. 49, no. 19, pp. 4121–4128, 2011. View at Publisher · View at Google Scholar · View at Scopus
  21. J. R. Whitfield, A. Morelli, and J. C. Warner, “Enzymatic reversal of polymeric thymine photocrosslinking with E. coli DNA photolyase,” Journal of Macromolecular Science Part A: Pure and Applied Chemistry, vol. 42, no. 11, pp. 1541–1546, 2005. View at Publisher · View at Google Scholar · View at Scopus
  22. V. I. Paz Zanini, F. Tulli, D. M. Martino, B. López de Mishima, and C. D. Borsarelli, “Improvement of the amperometric response to l-lactate by using a cationic bioinspired thymine polycation in a bioelectrode with immobilized lactate oxidase,” Sensors and Actuators B: Chemical, vol. 181, pp. 251–258, 2013. View at Publisher · View at Google Scholar · View at Scopus
  23. V. I. Paz Zanini, M. Gavilán, B. A. López De Mishima, D. M. Martino, and C. D. Borsarelli, “A highly sensitive and stable glucose biosensor using thymine-based polycations into laponite hydrogel films,” Talanta, vol. 150, pp. 646–654, 2016. View at Publisher · View at Google Scholar · View at Scopus
  24. P. T. Anastas and J. C. Warner, Green Chemistry: Theory and Practice, Oxford University Press, Oxford, UK, 1998.
  25. P. Zarras and O. Vogl, “Polycationic salts. 3. synthesis, styrene based trialkylammonium salts and their polymerization1-2,” Journal of Macromolecular Science A, vol. 37, no. 8, pp. 817–840, 2000. View at Publisher · View at Google Scholar
  26. J. R. Bianchini, K. Saito, T. B. Balin, V. Dua, and J. C. Warner, “Thymine-based, water-soluble phototerpolymers: their preparation and synthesis,” Journal of Polymer Science, Part A: Polymer Chemistry, vol. 45, no. 7, pp. 1296–1303, 2007. View at Publisher · View at Google Scholar · View at Scopus
  27. A. L. McLaughlin, Development of a method for characterizing synthetic polymer simples using gel permeation chromatography and poly-vinylbenzyl chloride standard curve [B.S. thesis], Simmons College, Boston, Mass, USA, 2012.
  28. S. A. Bortolato, A. L. Barbarini, R. M. Benitez, D. A. Estenoz, and D. M. Martino, “Photo-induced curing of thymine-based bioinspired polymers. A chemometric analysis,” Latin American Applied Research, vol. 43, pp. 329–336, 2013. View at Google Scholar
  29. S.-W. Kuo and R.-S. Cheng, “DNA-like interactions enhance the miscibility of supramolecular polymer blends,” Polymer, vol. 50, no. 1, pp. 177–188, 2009. View at Publisher · View at Google Scholar · View at Scopus
  30. A. Reiser and E. A. Pitts, “A photographic theory of crosslinking resists,” The Journal of Photographic Science, vol. 29, no. 5, pp. 187–191, 1981. View at Publisher · View at Google Scholar
  31. S. Trakhtenberg, A. S. Cannon, and J. C. Warner, “Chapter 13 non-catalytic photo-induced immobilization processes in polymer films,” Thin Films and Nanostructures, vol. 34, pp. 665–695, 2007. View at Publisher · View at Google Scholar
  32. J. Ledesma, S. A. Bortolato, C. E. Boschetti, and D. M. Martino, “Optimization of environmentally benign polymers based on thymine and polyvinyl sulfonate using plackett-burman design and surface response,” Journal of Chemistry, vol. 2013, Article ID 947137, 9 pages, 2013. View at Publisher · View at Google Scholar
  33. L. O. Searls, Synthesis and characterization of thymine-based photoresist polymers [B.S. thesis], Simmons College, Boston, Mass, USA, 2009.