Triphenylsulfonium triflate

Names

IUPAC name

Triphenylsulfonium triflate

Identifiers

CAS Registry Number

66003-78-9^N

ChemSpider

9904036^Y

InChI

InChI=1S/C18H15S.CHF3O3S/c1-4-10-16(11-5-1)19(17-12-6-2-7-13-17)18-14-8-3-9-15-18;2-1(3,4)8(5,6)7/h1-15H;(H,5,6,7)/q+1;/p-1^Y
Key: FAYMLNNRGCYLSR-UHFFFAOYSA-M^Y

Jmol-3D images

C1=CC=C(C=C1)[S+](C2=CC=CC=C2)C3=CC=CC=C3.C(F)(F)(F)S(=O)(=O)[O-]

Properties

Chemical formula

C₁₉H₁₅F₃O₃S₂

Molar mass

412.45 g/mol

Appearance

colourless solid

Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)

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Infobox references

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.^[1] The triphenylsulfonium salts absorb at 233 nm, which induces the series of reactions shown:^[2]

[(C₆H₅)₃S⁺][CF₃SO₃⁻] + hν → [(C₆H₅)₂S^+.][CF₃SO₃⁻] + C₆H₅^.

[(C₆H₅)₂S^+.][CF₃SO₃⁻] + C₆H₅^. → (C₆H₅C₆H₄)(C₆H₅)S + CF₃SO₃H

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

References

↑ 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.
↑ W. D. Hinsberg, G. M. Wallraff "Lithographic Resists" Kirk-Othmer Encyclopedia of Chemical Technology, Wiley-VCH, Weinheim, 2001. (Published online: 17 June, 2005)