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Issue 27, 2017
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(Oligo)aromatic species with one or two conjugated Si[double bond, length as m-dash]Si bonds: near-IR emission of anthracenyl-bridged tetrasiladiene

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Abstract

A series of aryl disilenes Tip2Si[double bond, length as m-dash]Si(Tip)Ar (2a–c) and para-arylene bridged tetrasiladienes, Tip2Si[double bond, length as m-dash]Si(Tip)–LU–Si(Tip)[double bond, length as m-dash]SiTip2 (3a–d) are synthesized by the transfer of the Tip2Si[double bond, length as m-dash]SiTip unit to aryl halides and dihalides by nucleophilic disilenides Tip2Si[double bond, length as m-dash]SiTipLi (Tip = 2,4,6-iPr3C6H2, Ar = aryl substituent, LU = para-arylene linking unit). The scope of the nucleophilic Si[double bond, length as m-dash]Si transfer reaction is demonstrated to also include substrates of considerable steric bulk such as mesityl or duryl halides Ar–X (Ar = Mes = 2,4,6-Me3C6H2; Ar = Dur = 2,3,5,6-Me4C6H, X = Br or I). Bridged tetrasiladienes Tip2Si[double bond, length as m-dash]Si(Tip)–LU–Si(Tip)[double bond, length as m-dash]SiTip2 with more extended linking units surprisingly exhibit fluorescence at room temperature, albeit weak. DFT calculations suggest that partial charge transfer character of the excited state is a possible explanation.

Graphical abstract: (Oligo)aromatic species with one or two conjugated Si [[double bond, length as m-dash]] Si bonds: near-IR emission of anthracenyl-bridged tetrasiladiene

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Article information


Submitted
01 Feb 2017
Accepted
29 Mar 2017
First published
29 Mar 2017

Dalton Trans., 2017,46, 8839-8848
Article type
Paper
Author version available

(Oligo)aromatic species with one or two conjugated Si[double bond, length as m-dash]Si bonds: near-IR emission of anthracenyl-bridged tetrasiladiene

N. M. Obeid, L. Klemmer, D. Maus, M. Zimmer, J. Jeck, I. Bejan, A. J. P. White, V. Huch, G. Jung and D. Scheschkewitz, Dalton Trans., 2017, 46, 8839
DOI: 10.1039/C7DT00397H

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