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An X‐ray photoelectron spectroscopic investigation of the selectivity of hydroxyl derivatization reactions

Publication ,  Journal Article
Chilkoti, A; Ratner, BD
Published in: Surface and Interface Analysis
January 1, 1991

The Selectivity of trifluoroacetic anhydride (TFAA), used for the vapor‐phase derivatization of hydroxyl groups in multifunctional oxygen‐containing polymeric surfaces, has been investigated by XPS studies on model epoxides systems. The reactivity of TFAA towards epoxides observed here is discussed in the context of the large amount of published literature implying high selectivity of this reaction towards hydroxyl groups. Acetyl chloride (AcCl) and heptafluorobutyryl chloride (HFBuCl), used to derivatize hydroxyl groups in the literature, were also examined, with regard to cross‐reaction with epoxides. Both AcCl and HFBuCl react with epoxides, forming chloroacetates and perfluorinated chloroacetates, respectively. Moreover, HFBuCl is shown to react with double bonds forming perfluorinated chloroacetates, while AcCl is unreactive towards them. The reactivity of HFBuCl to wards epoxides and unsaturation compromises its use as a derivatization reagent of hydroxyl groups. However, the unique reaction products formed by exposure of hydroxyls and epoxides to AcCl vapor may allow hydroxyl species to be distinguished from epoxides in multifunctional carbon‐oxygen polymeric surfaces. Copyright © 1991 John Wiley & Sons Ltd.

Duke Scholars

Published In

Surface and Interface Analysis

DOI

EISSN

1096-9918

ISSN

0142-2421

Publication Date

January 1, 1991

Volume

17

Issue

8

Start / End Page

567 / 574

Related Subject Headings

  • Applied Physics
  • 5104 Condensed matter physics
  • 4018 Nanotechnology
  • 0306 Physical Chemistry (incl. Structural)
  • 0204 Condensed Matter Physics
 

Citation

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Chilkoti, A., & Ratner, B. D. (1991). An X‐ray photoelectron spectroscopic investigation of the selectivity of hydroxyl derivatization reactions. Surface and Interface Analysis, 17(8), 567–574. https://doi.org/10.1002/sia.740170805
Chilkoti, A., and B. D. Ratner. “An X‐ray photoelectron spectroscopic investigation of the selectivity of hydroxyl derivatization reactions.” Surface and Interface Analysis 17, no. 8 (January 1, 1991): 567–74. https://doi.org/10.1002/sia.740170805.
Chilkoti A, Ratner BD. An X‐ray photoelectron spectroscopic investigation of the selectivity of hydroxyl derivatization reactions. Surface and Interface Analysis. 1991 Jan 1;17(8):567–74.
Chilkoti, A., and B. D. Ratner. “An X‐ray photoelectron spectroscopic investigation of the selectivity of hydroxyl derivatization reactions.” Surface and Interface Analysis, vol. 17, no. 8, Jan. 1991, pp. 567–74. Scopus, doi:10.1002/sia.740170805.
Chilkoti A, Ratner BD. An X‐ray photoelectron spectroscopic investigation of the selectivity of hydroxyl derivatization reactions. Surface and Interface Analysis. 1991 Jan 1;17(8):567–574.
Journal cover image

Published In

Surface and Interface Analysis

DOI

EISSN

1096-9918

ISSN

0142-2421

Publication Date

January 1, 1991

Volume

17

Issue

8

Start / End Page

567 / 574

Related Subject Headings

  • Applied Physics
  • 5104 Condensed matter physics
  • 4018 Nanotechnology
  • 0306 Physical Chemistry (incl. Structural)
  • 0204 Condensed Matter Physics