Synthesis of Polycyclic and Cage Siloxanes by Hydrolysis and Intramolecular Condensation of Alkoxysilylated Cyclosiloxanes

Tomoaki Sugiyama, Hiroya Shiba, Masashi Yoshikawa, Hiroaki Wada, Atsushi Shimojima, Kazuyuki Kuroda

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

The controlled synthesis of oligosiloxanes with well-defined structures is important for the bottom-up design of siloxane-based nanomaterials. This work reports the synthesis of various polycyclic and cage siloxanes by the hydrolysis and intramolecular condensation of monocyclic tetra- and hexasiloxanes functionalized with various alkoxysilyl groups. An investigation of monoalkoxysilylated cyclosiloxanes revealed that intramolecular condensation occurred preferentially between adjacent alkoxysilyl groups to form new tetrasiloxane rings. The study of dialkoxy- and trialkoxysilylated cyclotetrasiloxanes revealed multistep intramolecular condensation reactions to form cubic octasiloxanes in relatively high yields. Unlike conventional methods starting from organosilane monomers, intramolecular condensation enables the introduction of different organic substituents in controlled arrangements. So-called Janus cubes have been successfully obtained, that is, Ph 4 R 4 Si 8 O 12 , in which R=Me, OSiMe 3 , and OSiMe 2 Vi (Vi=vinyl). These findings will enable the creation of siloxane-based materials with diverse functions.

Original languageEnglish
Pages (from-to)2764-2772
Number of pages9
JournalChemistry - A European Journal
Volume25
Issue number11
DOIs
Publication statusPublished - 2019 Feb 21

Keywords

  • cage compounds
  • condensation reactions
  • intramolecular reactions
  • polycycles
  • siloxanes

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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