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Stereospecific reductive coupling polymerization of bis(benzylic gem-dibromide)s via formation of a trans-C<img border='0' src='http://www.rsc.org/images/entities/h2_char_e001.gif' alt='[double bond, length as m-dash]'/>C bond

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Abstract

Stereospecific polymers were constructed by the successive formation of a trans-C[double bond, length as m-dash]C bond using bis(benzylic gem-dibromide)s as monomers treated with Cu/polyamine under mild conditions. The structure of the polymer was characterized by GPC, NMR, UV-vis and MALDI-TOF-MS. The formation of a trans-C[double bond, length as m-dash]C bond was established by a series of control reactions. Evidence demonstrates that the C[double bond, length as m-dash]C bond is generated by two domino reactions, one is the intermolecular reductive coupling reaction from gem-dibromide to vicinal dibromide and the other is the intramolecular debromination of vicinal dibromide, and therefore, the formation of a trans-C[double bond, length as m-dash]C bond. The successive formation of the trans-C[double bond, length as m-dash]C bond leads to the growth of a polymer chain following a step-growth polymerization mechanism.

Graphical abstract: Stereospecific reductive coupling polymerization of bis(benzylic gem-dibromide)s via formation of a trans-C<img border='0' src='http://www.rsc.org/images/entities/char_e001.gif' alt='[double bond, length as m-dash]'/>C bond

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Publication details

The article was received on 29 Mar 2017, accepted on 03 Jun 2017 and first published on 05 Jun 2017


Article type: Paper
DOI: 10.1039/C7PY00525C
Citation: Polym. Chem., 2017, Advance Article
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    Stereospecific reductive coupling polymerization of bis(benzylic gem-dibromide)s via formation of a trans-C<img border='0' src='http://www.rsc.org/images/entities/h2_char_e001.gif' alt='[double bond, length as m-dash]'/>C bond

    H. Cao, Z. Liu and Q. Wang, Polym. Chem., 2017, Advance Article , DOI: 10.1039/C7PY00525C

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