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Exploiting direct heteroarylation polymerization homocoupling defects for the synthesis of a molecular dimer

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Abstract

We have utilized a C–H homocoupling defect that plagues direct heteroarylation polymerization reactions to access a molecular dimer based on diketopyrrolopyrrole and perylene diimide. This synthetic route, which also incorporates a direct heteroarylation mono-substitution, proved to be an effective method to access this class of compound. The dimer, PDI-DPP-DPP-PDI, presented an overall electron-deficient π-conjugated molecular framework with strong optical absorption from 400–800 nm. The low energy absorption from 600–800 nm is a feature not accessible by the monomeric analogue, highlighting the potential of this dimerization method to be used for spectral engineering of π-conjugated materials.

Graphical abstract: Exploiting direct heteroarylation polymerization homocoupling defects for the synthesis of a molecular dimer

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Publication details

The article was received on 06 Nov 2017, accepted on 26 Nov 2017 and first published on 27 Nov 2017


Article type: Paper
DOI: 10.1039/C7NJ04285J
Citation: New J. Chem., 2018, Advance Article
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    Exploiting direct heteroarylation polymerization homocoupling defects for the synthesis of a molecular dimer

    W. B. Breukelaar, S. M. McAfee and G. C. Welch, New J. Chem., 2018, Advance Article , DOI: 10.1039/C7NJ04285J

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