Potential photoacid generators based on oxime sulfonates

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Abstract

The bis-oxime of acenaphthenequinone and the mono-oxime of benzil have been sulfonated by reaction with 4-methylbenzenesulfonyl chloride and propylsulfonyl chloride. The four sulfonated oximes were characterised by X-ray single-crystal structure determinations. Some photochemical decompositions were studied using a 6-W 254-nm immersion well lamp in dichloromethane. The 4-methylbenzenesulfonate bis-oxime of acenaphthenequinone and the 4-methylbenzenesulfonate mono-oxime of benzil both give 4-methylbenzenesulfonic acid upon irradiation but not 4-methylbenzenesulfinic acid. Fragmentation pathways are discussed. The possible use of these compounds as photoacid generators in polymer resists and the role of secondary reactions to liberate acid is discussed.

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Plater, M. J., Harrison, W. T. A., & Killah, R. (2019). Potential photoacid generators based on oxime sulfonates. Journal of Chemical Research, 43(1–2), 26–33. https://doi.org/10.1177/1747519819831829

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