Effect of acid structure on deprotection of poly(2-trimethylsilyl-2-propyl methacrylate)

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Deprotection of poly(2-trimethylsilyl-2-propyl methacrylate) was studied for various photogenerated acids. Deprotection of 2-trimethylsilyl-2-propyl (TMSP) ester did not occur in a catalytic manner when the photogenerated acid possessing a fluoride ion source such as SbF6- or AsF6- was used. Because the cleaved product, alpha-methyl-alpha-(trimethylsilyl)ethyl cation, undergoes rearrangement through methyl migration from silicon to carbon with nucleophilic attack on the silicon by the fluoride ion, the acid was consumed in the reaction. Fortunately, when the counterion of the acid does not provide a fluoride ion, e.g. sulfonate, the carbonium ion undergoes elimination to produce 2,2,3-trimethyl-2-silabut-3-ene, and regenerates another acid. The thermal stability of TMSP ester was very similar to t-butyl ester, and acid catalyzed cleavage of the TMSP begins at 80 degrees C. (C) 1999 Elsevier Science Ltd. All rights reserved.
Publisher
ELSEVIER SCI LTD
Issue Date
1999-06
Language
English
Article Type
Article
Keywords

PHOTORESISTS

Citation

POLYMER, v.40, no.14, pp.4055 - 4061

ISSN
0032-3861
DOI
10.1016/S0032-3861(98)00632-6
URI
http://hdl.handle.net/10203/68451
Appears in Collection
CH-Journal Papers(저널논문)
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