Issue 5, 2013

Introduction of ferrocene-containing [2]rotaxanes onto siloxane, silsesquioxane and polysiloxanes via click chemistry

Abstract

The reaction of N3(CH2)3Si(OTMS)3 (TMS = SiMe3) with a dialkylammonium having hexynyl group 1, [FcCH2NH2CH2C6H4-4-O(CH2)4C[triple bond, length as m-dash]CH]PF6 (Fc = Fe(C5H4)(C5H5)), in the presence of dibenzo[24]crown-8-ether (DB24C8) and [Cu{Fe(CN)4}]PF6 catalyst yielded the [2]rotaxane containing the dialkylammonium unit terminated by a bulky silyl group. Azides with a silsesquioxane group react similarly to form the corresponding [2]rotaxanes having a bulky silsesquioxane end group. The azide-functionalized polysiloxane, [–O–SiMe{(CH2)3N3}–]n[–O–SiMe2–]m also undergoes a click reaction with 1 to produce the side chain polyrotaxane. Cyclic voltammograms of these rotaxanes and 1 [(DB24C8)1] show the Fe(II)/Fe(III) redox at the same potential, but with different current depending on their molecular weights. Addition of PdCl2(MeCN)2 to a solution of the side-chain polyrotaxane forms gel which regenerates the sol upon addition of PPh3.

Graphical abstract: Introduction of ferrocene-containing [2]rotaxanes onto siloxane, silsesquioxane and polysiloxanes via click chemistry

Supplementary files

Article information

Article type
Paper
Submitted
29 Jun 2012
Accepted
03 Oct 2012
First published
04 Oct 2012

Dalton Trans., 2013,42, 1476-1482

Introduction of ferrocene-containing [2]rotaxanes onto siloxane, silsesquioxane and polysiloxanes via click chemistry

G. Yu, Y. Suzaki, T. Abe and K. Osakada, Dalton Trans., 2013, 42, 1476 DOI: 10.1039/C2DT31406A

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