Abstract
Diketopyrrolopyrrole (DPP) is an important type of π-conjugated building block for high-performance organic electronic materials. DPP-based conjugated materials are usually synthesized via Suzuki, Stille, or Negishi cross-coupling reactions, which require organometallic precursors. In this paper, a series of novel phenyl-cored DPP molecules, including five meta-phenyl-cored molecules and four para-phenyl-cored molecules, have been synthesized in moderate to good yields, in a facile manner, through the Pd-catalyzed direct arylation of C–H bonds, and their optoelectrical properties have been investigated in detail. All new molecules have been fully characterized by NMR, MALDI-TOF MS, elemental analysis, UV–visible spectroscopy, and cyclic voltammetry. This synthetic strategy has evident advantages of atom- and step-economy and low cost, compared with traditional cross-coupling reactions.
Highlights
IntroductionConjugated materials play an irreplaceable role in the field of optics and organic electronics
Introduction πConjugated materials play an irreplaceable role in the field of optics and organic electronics.π-Conjugated organic materials can be divided into polymers, oligomers (MW > 1000) and small molecules (MW < 1000) [1]
The direct arylation coupling between DPP and the p-dibromobenzene derivatives, 1,4-dibromo-2,3-difluorobenzene, 1,4-dibromo-2,5-difluorobenzene, 1,4-dibromo-2,5-dichlorobenzene, and 1,4-dibromo-2,5-dimethoxy benzene, produced DPP-based molecules Ms6~9, respectively, with
Summary
Conjugated materials play an irreplaceable role in the field of optics and organic electronics. Π-Conjugated organic materials can be divided into polymers (molecular weight MW > 10,000), oligomers (MW > 1000) and small molecules (MW < 1000) [1]. 1976 [2], π-conjugated polymers, oligomers, and small molecules have drawn extensive attention from researchers. The small molecules have defined structures, their conjugation lengths and molecular weights are limited. The oligomers can be regarded as a kind of special polymer with monodispersity (PDI = 1) and defined structure which might combine the advantages of polymers and small molecules while overcoming their individual shortcomings [3,4]. Oligomers with defined structure and high molecular weight are expected to be ideal choices for organic π-conjugated functional materials
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