Triphenylsulfonium triflate

Triphenylsulfonium triflate

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ImageFile=Ph3SOTf.pngImageSize=300px
IUPACName=Triphenylsulfonium triflate
OtherNames=
Section1= Chembox Identifiers
CASNo=66003-78-9
PubChem=24874589
SMILES=C1=CC=C(C=C1)C(=O)C(=O)O

Section2= Chembox Properties
Formula=C19H15F3O3S2
MolarMass=412.45 g/mol
Appearance= colourless solid
Density=
MeltingPt=
BoilingPt=
Solubility=

Section3= Chembox Hazards
MainHazards=
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Triphenylsulfonium triflate is the chemical compound with the formula [(C6H5)3S] [CF3SO3] . This colourless salt consists of a sulfonium cation and the triflate anion. Many related salts are known including those with other noncoordinating anions and those with diverse substituents on the phenyl rings.

These compounds are "photoacids," releasing strong acids upon photolysis, which is useful in photolithography. [J. V. Crivello "The Discovery and Development of Onium Salt Cationic Photoinitiators" Journal of Polymer Science: Part A: Polymer Chemistry, 1999, Volume 37, pp. 4241–4254. DOI CCC 0887-624X/99/234241-14.] The triphenylsulfonium salts absorb at 233 nm, which induces the series of reactions shown: [W. D. Hinsberg, G. M. Wallraff "Lithographic Resists" Kirk-Othmer Encyclopedia of Chemical Technology, Wiley-VCH, Weinheim, 2001. (Published online: 17 June, 2005)]

: [(C6H5)3S+] [CF3SO3-] + "h"ν → [(C6H5)2S+.] [CF3SO3- + C6H5.: [(C6H5)2S+.] [CF3SO3-] + C6H5. → (C6H5C6H4)(C6H5)S + CF3SO3H

In a typical application, photoacids catalyze the polymerization of epoxides.

References


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