Citation: Yu Liang, Xiaopei Deng, Jay J. Senkevich, Hao Ding, Joerg Lahann. Thermal and environmental stability of poly(4-ethynyl-p-xylylene-co-p-xylylene) thin films[J]. Chinese Chemical Letters, ;2015, 26(4): 459-463. doi: 10.1016/j.cclet.2015.01.018 shu

Thermal and environmental stability of poly(4-ethynyl-p-xylylene-co-p-xylylene) thin films

1.
a Department of Material Science and Engineering, China University of Geosciences (Beijing), Beijing 100083, China;
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b Department of Chemical Engineering, University of Michigan, Ann Arbor, MI 48109, USA;
3.
c Massachusetts Institute of Technology, Institute for Soldier Nanotechnologies, Cambridge, MA 02139, USA

Corresponding author: Joerg Lahann,
Received Date: 4 November 2014
Available Online: 6 January 2015
Fund Project:

The aim of this paper was to test the thermal and environmental stability of poly(4-ethynyl-p-xylyleneco- p-xylylene) thin films prepared by chemical vapor deposition (CVD) and to optimize the reaction conditions of the polymer. Fourier transformed infrared spectroscopy (FTIR), thermogravimetric analysis (TGA) and fluorescence microscopy were employed to investigate the stability of the reactive polymer coatings in various environmental conditions. Chemical reactivity of the thin films were then tested by Huisgen 1,3-dipolar cycloaddition reaction ("click" reaction). The alkyne functional groups on poly(4- ethynyl-p-xylylene-co-p-xylylene) thin films were found to be stable under ambient storage conditions and thermally stable up to 100℃ when annealed at 0.08 Torr in argon. We also optimized the click reaction conditions of azide-functionalized molecules with poly(4-ethynyl-p-xylylene-co-p-xylylene). The best reaction result was achieved, when copper concentration was 0.5 mmol/L, sodium ascorbate concentration to copper concentration was 5:1. In contrast, the azide concentration and temperature had no obvious effect on the surface reaction.
- Chemical vapor deposition,
- Poly(4-ethynyl-p-xylylene-co-p-xylylene),
- Thermal stability,
- Environmental stability,
- Click reaction
1. [1]
  [1] W.F. Gorham, A new, general synthetic method for the preparation of linear polyp- xylylenes, J. Polym. Sci. Part A: Polym. Chem. 4 (1966) 3027-3039.
2. [2]
  [2] J. Lahann, R. Langer, Novel poly(p-xylylenes): thin films with tailored chemical and optical properties, Macromolecules 35 (2002) 4380-4386.
3. [3]
  [3] M.E. Alf, A. Asatekin, M.C. Barr, et al., Chemical vapor deposition of conformal, functional, and responsive polymer films, Adv. Mater. 22 (2010) 1993-2027.
4. [4]
  [4] A. Greiner, Poly(1,4-xylylene)s: polymer films by chemical vapour deposition, Trends Polym. Sci. 5 (1997) 12-16.
5. [5]
  [5] J. Lahann, R. Langer, Surface-initiated ring-opening polymerization of epsiloncaprolactone from a patterned poly(hydroxymethyl-p-xylylene), Macromol. Rapid Commun. 22 (2001) 968-971.
6. [6]
  [6] J. Lahann, I.S. Choi, J. Lee, K.F. Jenson, R. Langer, A new method toward microengineered surfaces based on reactive coating, Angew. Chem. Int. Ed. 40 (2001) 3166-3169.
7. [7]
  [7] H. Nandivada, H.Y. Chen, J. Lahann, Vapor-based synthesis of poly[(4-formyl-pxylylene)- co-(p-xylylene)] and its use for biomimetic surface modifications, Macromol. Rapid Commun. 26 (2005) 1794-1799.
8. [8]
  [8] H.-Y. Chen, J. Lahann, Designable biointerfaces using vapor-based reactive polymers, Langmuir 27 (2011) 34-48.
9. [9]
  [9] J. Lahann, M. Balcells, H. Lu, et al., Reactive polymer coatings: a first step toward surface engineering of microfluidic devices, Anal. Chem. 75 (2003) 2117-2122.
10. [10]
  [10] M.-Y. Tsai, C.-Y. Lin, C.-H. Huang, et al., Vapor-based synthesis of maleimidefunctionalized coating for biointerface engineering, Chem. Commun. 48 (2012) 10969-10971.
11. [11]
  [11] Y. Elkasabi, M. Yoshida, H. Nandivada, H.-Y. Chen, J. Lahann, Towards multipotent coatings: chemical vapor deposition and biofunctionalization of carbonyl-substituted copolymers, Macromol. Rapid Commun. 29 (2008) 855-870.
12. [12]
  [12] X.P. Deng, J. Lahann, Orthogonal surface functionalization through bioactive vapor-based polymer coatings, J. Appl. Polym. Sci. 131 (2014) 40315.
13. [13]
  [13] H. Nandivada, H.Y. Chen, L. Bondarenko, J. Lahann, Reactive polymer coatings that "click", Angew. Chem. Int. Ed. 45 (2006) 3360-3363.
14. [14]
  [14] X. Jiang, H.Y. Chen, G. Galvan, M. Yoshida, J. Lahann, Vapor-based initiator coatings for atom transfer radical polymerization, Adv. Funct. Mater. 18 (2008) 27-35.
15. [15]
  [15] X. Deng, C. Friedmann, J. Lahann, Bio-orthogonal "double-click" chemistry based on multifunctional coatings, Angew. Chem. Int. Ed. 50 (2011) 6522-6526.
16. [16]
  [16] X. Zhang, Y. Zhang, Applications of azide-based bioorthogonal click chemistry in glycobiology, Molecules 18 (2013) 7145-7159.
17. [17]
  [17] J.E. Moses, A.D. Moorhouse, The growing applications of click chemistry, Chem. Soc. Rev. 36 (2007) 1249-1262.
18. [18]
  [18] K.K. Ghosh, H.H. Ha, N.Y. Kang, Y. Chandran, Y.T. Chang, Solid phase combinatorial synthesis of a xanthone library using click chemistry and its application to an embryonic stem cell probe, Chem. Commun. 47 (2011) 7488-7490.
19. [19]
  [19] H. Kolb, M. Finn, K. Sharpless, Click chemistry: diverse chemical function from a few good reactions, Angew. Chem. 40 (2001) 2004-2021.
20. [20]
  [20] C.D. Hein, X. Liu, D. Wang, Click chemistry, a powerful tool for pharmaceutical sciences, Pharm. Res. 25 (2008) 2216-2230.
21. [21]
  [21] J.-F. Lutz, 1,3-Dipolar cycloadditions of azides and alkynes: a universal ligation tool in polymer and materials science, Angew. Chem. 46 (2007) 1018-1025.
22. [22]
  [22] M. Meldal, C.W. Tornoe, Cu-catalyzed azide-alkyne cycloaddition, Chem. Rev. 108 (2008) 2952-3015.
23. [23]
  [23] M.G. Finn, H.C. Kolb, V.V. Fokin, K.B. Sharpless, Click chemistry-definition and aims, Prog. Chem. 20 (2008) 1-5.
24. [24]
  [24] J.J. Senkevich, Stability of CVD-produced polymer thin films, Chem. Vapor Depos. 17 (2011) 170-172.
25. [25]
  [25] J.J. Senkevich, B.W. Woods, J.J. McMahon, P.I. Wang, Thermomechanical properties of parylene X, a room-temperature chemical vapor depositable crosslinkable polymer, Chem. Vapor Depos. 13 (2007) 55-59.
26. [26]
  [26] X.P. Deng, T.W. Eyster, Y. Elkasabi, J. Lahann, Bio-orthogonal polymer coatings for co-presentation of biomolecules, Macromol. Rapid Commun. 33 (2012) 640-645.
27. [27]
  [27] J.E. Hein, V.V. Fokin, Copper-catalyzed azide-alkyne cycloaddition (CuAAC) and beyond: new reactivity of copper(I) acetylides, Chem. Soc. Rev. 39 (2010) 1302- 1315.
28. [28]
  [28] V. Hong, N.F. Steinmetz, M. Manchester, M.G. Finn, Labeling live cells by coppercatalyzed alkyne-azide click chemistry, Bioconjug. Chem. 21 (2010) 1912-1916.
29. [29]
  [29] V.V. Rostovtsev, L.G. Green, V.V. Fokin, K.B. Sharpless, A stepwise Huisgen cycloaddition process: copper(I)-catalyzed regioselective "ligation" of azides and terminal alkynes, Angew. Chem. 114 (2002) 2708-2711.
30. [30]
  [30] V. Hong, S.I. Presolski, C. Ma, M.G. Finn, Analysis and optimization of coppercatalyzed azide-alkyne cycloaddition for bioconjugation, Angew. Chem. Int. Ed. 48 (2009) 9879-9883.
31. [31]
  [31] J. González, V.M. Pérez, D.O. Jiménez, et al., Effect of temperature on triazole and bistriazole formation through copper-catalyzed alkyne-azide cycloaddition, Tetrahedron Lett. 52 (2011) 3514-3517.
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