Potential photoacid generators based on oxime sulfonates

M John Plater; William T A Harrison; Ross Killah

doi:10.1177/1747519819831829

Potential photoacid generators based on oxime sulfonates

M John Plater (Corresponding Author), William T A Harrison, Ross Killah

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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.

Original language	English
Pages (from-to)	26-33
Number of pages	9
Journal	Journal of Chemical Research
Volume	43
Issue number	1-2
DOIs	https://doi.org/10.1177/1747519819831829
Publication status	Published - 13 May 2019

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Keywords

photoacid generator (PAG)
oxime sulfonates
acenaphthenequinone
benzil
Benzil
Acenaphthenequinone
Oxime sulfonates
Photoacid generator

ASJC Scopus subject areas

Chemistry(all)

Cite this

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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title = "Potential photoacid generators based on oxime sulfonates",

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.",

keywords = "photoacid generator (PAG), oxime sulfonates, acenaphthenequinone, benzil, Benzil, Acenaphthenequinone, Oxime sulfonates, Photoacid generator",

author = "Plater, {M John} and Harrison, {William T A} and Ross Killah",

note = "We are grateful to the National Mass Spectrometry Foundation, University of Swansea, and to the National Crystallographic Service Center, University of Southampton.",

year = "2019",

month = may,

day = "13",

doi = "10.1177/1747519819831829",

language = "English",

volume = "43",

pages = "26--33",

journal = "Journal of Chemical Research",

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TY - JOUR

T1 - Potential photoacid generators based on oxime sulfonates

AU - Plater, M John

AU - Harrison, William T A

AU - Killah, Ross

N1 - We are grateful to the National Mass Spectrometry Foundation, University of Swansea, and to the National Crystallographic Service Center, University of Southampton.

PY - 2019/5/13

Y1 - 2019/5/13

N2 - 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.

AB - 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.

KW - photoacid generator (PAG)

KW - oxime sulfonates

KW - acenaphthenequinone

KW - benzil

KW - Benzil

KW - Acenaphthenequinone

KW - Oxime sulfonates

KW - Photoacid generator

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UR - http://www.mendeley.com/research/potential-photoacid-generators-based-oxime-sulfonates

U2 - 10.1177/1747519819831829

DO - 10.1177/1747519819831829

M3 - Article

VL - 43

SP - 26

EP - 33

JO - Journal of Chemical Research

JF - Journal of Chemical Research

SN - 0308-2342

IS - 1-2

ER -

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Accepted Manuscript
This article has been accepted for publication in Journal of Chemical Research, 2019, 43(1-2), pp.26-33, https://doi.org/10.1177%2F1747519819831829 published by Science Reviews 2000 Ltd.
Accepted author manuscript, 781 KBLicence: Other