Beilstein Journal of Organic Chemistry, ( ISI ), Volume (6), No (57), Year (2010-5) , Pages (1-9)

Title : ( Polar tagging in the synthesis of monodisperse oligo(p-phenyleneethynylene)s and an update on the synthesis of oligoPPEs )

Authors: Dhananjaya Sahoo , Susanne Thiele , Miriam Schulte , Navid Ramezanian , Adelheid Godt ,

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Abstract

Abstract One important access to monodisperse (functionalized) oligoPPEs is based on the orthogonality of the alkyne protecting groups triisopropylsilyl and hydroxymethyl (HOM) and on the polar tagging with the hydroxymethyl moiety for an easy chromatographic separation of the products. This paper provides an update of this synthetic route. For the deprotection of HOM protected alkynes, γ-MnO2 proved to be better than (highly) activated MnO2. The use of HOM as an alkyne protecting group is accompanied by carbometalation as a side reaction in the alkynyl–aryl coupling. The extent of carbometalation can be distinctly reduced through substitution of HOM for 1-hydroxyethyl. The strategy of polar tagging is extended by embedding ether linkages within the solubilising side chains. With building blocks such as 1,4-diiodo-2,5-bis(6-methoxyhexyl) less steps are needed to assemble oligoPPEs with functional end groups and the isolation of pure compounds becomes simple. For the preparation of 1,4-dialkyl-2,5-diiodobenzene a better procedure is presented together with the finding that 1,4-dialkyl-2,3-diiodobenzene, a constitutional isomer of 1,4-dialkyl-2,5-diiodobenzene, is one of the byproducts.

Keywords

, oligo(p, phenyleneethynylene)s
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@article{paperid:1030543,
author = {Dhananjaya Sahoo and Susanne Thiele and Miriam Schulte and Ramezanian, Navid and Adelheid Godt},
title = {Polar tagging in the synthesis of monodisperse oligo(p-phenyleneethynylene)s and an update on the synthesis of oligoPPEs},
journal = {Beilstein Journal of Organic Chemistry},
year = {2010},
volume = {6},
number = {57},
month = {May},
issn = {1860-5397},
pages = {1--9},
numpages = {8},
keywords = {oligo(p-phenyleneethynylene)s},
}

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%0 Journal Article
%T Polar tagging in the synthesis of monodisperse oligo(p-phenyleneethynylene)s and an update on the synthesis of oligoPPEs
%A Dhananjaya Sahoo
%A Susanne Thiele
%A Miriam Schulte
%A Ramezanian, Navid
%A Adelheid Godt
%J Beilstein Journal of Organic Chemistry
%@ 1860-5397
%D 2010

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