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Issue 8, 2013
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C–H activation: making diketopyrrolopyrrole derivatives easily accessible

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Abstract

Diketopyrrolopyrrole (DPP) derivatives are an important class of high-performance pigment used in inks, paints, plastics, and organic electronics. Until now, DPP derivatives containing sophisticated aryl units at the DPP core have usually been obtained via Suzuki, Stille, or Negishi cross-coupling reactions, which require organometallic precursors. In this work, a series of DPP-based π-conjugated molecules bearing diverse aryl substituents on the thiophene- or benzene-DPPs were facilely synthesized in moderate to excellent yields through the Pd-catalyzed direct arylation of C–H bonds. The synthetic procedures feature advantages over traditional C–C cross-coupling reactions such as: (1) avoidance of the use of organometallic reagents in the starting materials leading to simpler byproducts and higher atom economy, (2) fewer synthetic steps, (3) higher yields, (4) better compatibility with chemically sensitive functional groups, and (5) simpler catalytic systems free of phosphine ligands. These advantages make the present protocol an ideal and versatile strategy for the synthesis of DPP derivatives, especially for structurally complicated DPPs that may possess chemically sensitive functionalities. The optical and electrochemical properties of the synthesized DPPs (17 compounds) were systematically investigated using UV-vis spectroscopy, steady-state fluorescence spectroscopy, and cyclic voltammetry (CV).

Graphical abstract: C–H activation: making diketopyrrolopyrrole derivatives easily accessible

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Publication details

The article was received on 30 Nov 2012, accepted on 21 Dec 2012 and first published on 21 Dec 2012


Article type: Paper
DOI: 10.1039/C2TA01318E
Citation: J. Mater. Chem. A, 2013,1, 2795-2805
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    C–H activation: making diketopyrrolopyrrole derivatives easily accessible

    S. Liu, M. Shi, J. Huang, Z. Jin, X. Hu, J. Pan, H. Li, A. K.-Y. Jen and H. Chen, J. Mater. Chem. A, 2013, 1, 2795
    DOI: 10.1039/C2TA01318E

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