Chapter 106. The Use of a Silicone-Bonded Azo Dye as Chemical Proton Detector

  1. Prof. Norbert Auner3 and
  2. Prof. Johann Weis4
  1. U. Müller1 and
  2. A. Utterodt3,†

Published Online: 28 APR 2008

DOI: 10.1002/9783527619917.ch106

Organosilicon Chemistry IV: From Molecules to Materials

Organosilicon Chemistry IV: From Molecules to Materials

How to Cite

Müller, U. and Utterodt, A. (2000) The Use of a Silicone-Bonded Azo Dye as Chemical Proton Detector, in Organosilicon Chemistry IV: From Molecules to Materials (eds N. Auner and J. Weis), Wiley-VCH Verlag GmbH, Weinheim, Germany. doi: 10.1002/9783527619917.ch106

Editor Information

  1. 3

    Inst. für Anorganische Chemie, der Universität Frankfurt, Marie-Curie-Strasse 11, D-60439 Frankfurt am Main, Germany, Phone: 0 69/7 98-29180, -29591, Fax: 069/798-29188

  2. 4

    Wacker-Chemie GmbH, Geschäftsbereich S, Werk Burghausen, Johannes-Hess-Strasse 24, D-84489 Burghausen, Germany

Author Information

  1. 1

    Institut für Organische Chemie Martin-Luther-Universität Halle- Wittenberg Geusaer Straße, D-06217 Merseburg, Germany Tel.: Int. code + (3461)462009 — Fax.: Int. code + (3461)462081

  2. 3

    Inst. für Anorganische Chemie, der Universität Frankfurt, Marie-Curie-Strasse 11, D-60439 Frankfurt am Main, Germany, Phone: 0 69/7 98-29180, -29591, Fax: 069/798-29188

  1. Institut für Physikalische Chemie, Universität Jena, D-07743 Jena, Germany

Publication History

  1. Published Online: 28 APR 2008
  2. Published Print: 17 JAN 2000

ISBN Information

Print ISBN: 9783527298549

Online ISBN: 9783527619917

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Keywords:

  • proton;
  • acid;
  • detection;
  • diazonium salt;
  • azo dye

Summary

Quantitative determination of protons in nonaqueous solvents is of special interest in many fields of investigation like cation-induced photopolymerization and photocatalysis. In this way we checked an azo dye as a proton detector for the determination of protons in several organic solvents (methanol, acetonitrile, dimethoxyethane). To prevent characteristic problems of the photochemical investigations (quenching, sensitization) it was advantageous to separate the probe dye from the sample by fixing into a polymer matrix of a silicone network. For this purpose a 4–(N-allyl-N-methyl)aminoazobenzene was added to a H-functionalized siloxane by Pt catalysis. The remaining Si-H groups were crosslinked to a siloxane monomer containing vinyl ether groups. This polymer allows the application of the probe system in organic solvents without any restriction. The detection can be done by common UV-Vis spectroscopy. In spite of a low microviscosity of siloxanes, the equilibrium of the protonation is reached in a few seconds. Experiments were carried out with HCI gas, HCl in water and solutions of HCI, p-toluenesulfonic acid, and tetrafluoroboric acid diethyl ether complex in 1, 2–dimethoxyethane. In contrast to a homogeneous solution of the dye and an onium salt misinterpretations by photogenerated carbocation species can be excluded.