Hostname: page-component-cd9895bd7-lnqnp Total loading time: 0 Render date: 2024-12-25T17:25:37.097Z Has data issue: false hasContentIssue false
  • English
  • Français

Triggered Depolymerization of Poly(Phenylcarbamate)-based Materials in Response to Orthogonal Stimuli

Published online by Cambridge University Press:  31 May 2017

Ahmed-Rufai Ibrahim  and
Valerie Sheares Ashby
Ahmed-Rufai Ibrahim*
Affiliation:
University of North Carolina at Chapel Hill, Department of Chemistry, Chapel Hill, NC, 27599
Valerie Sheares Ashby
Affiliation:
University of North Carolina at Chapel Hill, Department of Chemistry, Chapel Hill, NC, 27599 Duke University, Department of Chemistry, Durham, NC, 27703
*
*(Email: [email protected])
Get access

Abstract

The synthesis of a polyacetal-block-polyurethane copolymer was achieved which possesses the ability to depolymerize both selectively and in response to orthogonal stimuli, heat and pH. To utilize heat as a stimulus, poly(phthalaldehyde) (PPA) was used as a block of the copolymer, while poly(benzyl-4-hydroxymethylphenylcarbamate) (PPC) end-capped with a tert-butoxycarbonyl protecting group (Boc group) were explored for viability as a pH-responsive block. The stimulus-induced depolymerization was studied using nuclear magnetic resonance (NMR), gel permeation chromatography (GPC), and attenuated total reflectance infrared spectroscopy (ATR-IR). These techniques confirmed that the depolymerization event did not affect the nature of the neighboring polymeric block. Depolymerization kinetics were measured for various chain lengths of each block. The results are presented and discussed to explore the ability of these materials to depolymerize in a controlled manner depending on the magnitude of the stimulus, as well as the ability for the blocks to remain unaffected by the orthogonal stimulus. This work shows promise for the development of advanced coatings systems and drug delivery applications.

Keywords

chemical synthesispolymerizationkinetics
Type
Articles
Information
MRS Advances , Volume 2 , Issue 47: Soft Materials and Biomaterials , 2017 , pp. 2513 - 2519
Copyright
Copyright © Materials Research Society 2017 

Access options

Get access to the full version of this content by using one of the access options below. (Log in options will check for institutional or personal access. Content may require purchase if you do not have access.)

References

REFERENCES

Ratner, B., Hoffman, A., Schoen, F., Lemons, J., Biomaterials Science 3, 179–181 (2012).Google Scholar
Xie, J., Lee, S., Chen, X., Adv. Drug Del. Rev. 11, 1064–1079 (2010).CrossRefGoogle Scholar
Stevens, M.P., Polymer Chemistry: an Introduction , 3 rd ed. (Oxford University Press, New York, 1999) p.193–194.Google Scholar
Shabat, D.J., Polym, J.. Sci., Part A: Polym. Chem. 44, 1569–1578 (2006).CrossRefGoogle Scholar
Peterson, G.I., Larsen, M.B., Boydston, A.J., Macromolecules 45, 7317–7328 (2012).CrossRefGoogle Scholar
Weinstain, R., Sagi, A., Karton, N., Shabat, D., Chem. Eur. J. 14, 6857–6861 (2008).CrossRefGoogle Scholar
Weinstain, R., Baran, P.S., Shabat, D., Bioconjugate Chem. 20, 1783–1791 (2009).CrossRefGoogle Scholar
Zheng, H., Yeung, K., Robbins, J.S., Paylick, R. A., Wu, M., Liu, R., Sen, A., Phillips, S. T., Angew. Chem. Int. Ed. 51, 2400–2404 (2012).CrossRefGoogle Scholar
DeWit, M.A. and Gillies, E.R., J. Am. Chem. Soc. 131, 18327–18334 (2009).CrossRefGoogle Scholar
Seo, W. and Phillips, S.T., J. Am. Chem. Soc. 132, 9234–9235 (2010).CrossRefGoogle Scholar
DeWit, M.A., Beaton, A., Gilies, E.R., J. Polym. Sci. Part A: Polym. Chem. 48, 3977–3985 (2010).CrossRefGoogle Scholar
De Gracia Lux, C., McFearin, C., Sankaranarayanan, J., Fomina, A., Almutari, A., ACS Macro Lett. 1, 922–926 (2012).CrossRefGoogle Scholar
DiLauro, A.M., Zhang, H., Baker, M.S., Wong, F., Sen, A., Phillips, S.T., Macromolecules 46, 7257–7265 (2013).CrossRefGoogle Scholar
DiLauro, A.M. and Phillips, S.T., Polym. Chem. 6, 3252–3258 (2015).CrossRefGoogle Scholar
Hernandez, H.L., Kang, S.K., Lee, O.P., Hwang, S.W., Kaitz, J.A., Advanced Materials 26, 7637–7642 (2014).CrossRefGoogle Scholar
Blencowe, C.A., Russell, A.T., Greco, F., Hayes, W., Thornthwaite, D.W., Polym. Chem. 2, 773–781 (2011).CrossRefGoogle Scholar
Binauld, S. and Stenzel, M.H., Chem. Commun. 49, 2082 (2013).CrossRefGoogle Scholar
Zhao, C., Nie, S., Tang, M., Sun, S., Prog. Polym. Sci. 36, 1499 (2011).CrossRefGoogle Scholar
Park, I.-K., Singha, K., Arote, R.B., Choi, Y.-J., Kim, W.J., Cho, C.-S., Macromol. Rapid Commun. 31, 1122 (2010).CrossRefGoogle Scholar
Gao, W., Chan, J.M., Farokzhad, O.C., C. Mol. Pharm. 7, 1913 (2010).CrossRefGoogle Scholar
Supplementary material: File

Ibrahim and Ashby supplementary material

Ibrahim and Ashby supplementary material 1

Download Ibrahim and Ashby supplementary material(File)
File 7.6 MB