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    Synthesis of functional derivatives of stereoregular organocyclosilsesquioxanes by thiol-ene addition

    Year: 2021

    Journal: J. Organomet. Chem., Volume 954, DEC 1

    Authors: Vysochinskaya, Yulia; Anisimov, Anton; Krylov, Fedor; Buzin, Mikhail; Buzin, Alexander; Peregudov, Alexander; Shchegolikhina, Olga; Muzafarov, Aziz

    Organizations: RFBR [19-29-13031]; INEOS RAS; Ministry of Science and Higher Education of the Russian Federation

    Keywords: Metallasiloxanes; Stereoregular organocyclosilsesquioxanes; Thiolene addition

    The paper presents a facile and convenient thiol-ene addition method for the modification of cis-tetravinylcyclotetrasiloxanes containing trimethylsiloxy or dimethyl(vinyl)siloxy units at the silicon atoms. As a result, amphiphilic derivatives with hydrophobic trimethylsilyl groups on one side of the cyclosiloxane ring and with polar hydrophilic groups on the other side were obtained, along with a totally hydrophilic eight-functional derivative and a fully hydrophobic one. All the compounds were obtained in almost quantitative yields and were fully characterized by H-1, C-13, Si-29 NMR, IR spectroscopy, and HRMS ESI. The thermal properties of the organocyclosilsesquioxanes obtained and their behavior at the water/air interface were studied. (C) 2021 Elsevier B.V. All rights reserved.
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