Potential photoacid generators based on oxime sulfonates

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

Research output: Contribution to journalArticle

2 Downloads (Pure)

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 languageEnglish
Pages (from-to)26-33
Number of pages9
JournalJournal of Chemical Research
Volume43
Issue number1-2
DOIs
Publication statusPublished - 13 May 2019

Fingerprint

Oximes
Chlorides
Acids
Methylene Chloride
Electric lamps
Polymers
Crystal structure
Irradiation
Single crystals
Decomposition
X rays

Keywords

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

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Potential photoacid generators based on oxime sulfonates. / Plater, M John (Corresponding Author); Harrison, William T A; Killah, Ross.

In: Journal of Chemical Research, Vol. 43, No. 1-2, 13.05.2019, p. 26-33.

Research output: Contribution to journalArticle

@article{89688ffef727439b8bad78b5e8457783,
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 = "5",
day = "13",
doi = "10.1177/1747519819831829",
language = "English",
volume = "43",
pages = "26--33",
journal = "Journal of Chemical Research",
issn = "0308-2342",
publisher = "Science Reviews Ltd",
number = "1-2",

}

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

UR - http://www.scopus.com/inward/record.url?scp=85066130858&partnerID=8YFLogxK

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 -