Direct core functionalisation of naphthalenediimides by iridium catalysed C–H borylation

Lyall, Catherine L.; Shotton, Camilla C.; Perez‐Salvia, Monserrat; Pantoş, G. Dan; Lewis, Simon E.

doi:10.1039/c4cc06522k

Cited by 14 publications

(8 citation statements)

References 89 publications

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“…Herein we select naphthalene diimides (NDIs) and biphenyl as the building blocks to directly construct the large twistacenes by a domino reaction for multiple C−C bond formation. The starting materials monoborylated NDI 1 and diborylated NDI 2 were synthesized under improved reaction condition of a reported method . There is no isomer for diborylated NDI 2 , which has been confirmed by the 1 H NMR spectrum (see the Supporting Information).…”

Section: Figurementioning

confidence: 78%

A Decatwistacene with an Overall 170° Torsion

et al. 2017

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Two different lengths of twistacenes, namely hexatwistacene and decatwistacene, induced by steric hindrance between imide groups and neighboring annulated benzene rings, were synthesized by bottom-up synthesis of palladium-catalyzed Suzuki cross-coupling and C-H activation. Single-crystal X-ray analyses revealed that decatwistacene, which is the longest twistacene reported, exhibits an astonishing overall end-to-end torsion angle of about 170°, the largest torsion angle reported. Both twistacenes have an enhanced solubility and stability with respect to light and oxygen owing to their large twisting deformations together with much lower LUMO levels caused by the introduction of imide groups, opening a window to the narrowest chiral graphene nanoribbons with good stability and processability.

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Section: Figurementioning

confidence: 78%

A Decatwistacene with an Overall 170° Torsion

et al. 2017

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“…13−16 Among the class of rylene diimides, perylene diimides (PDIs) have been investigated with respect to C–H activation, 17−22 and isolated reports dealing with the C–H activation of naphthalene diimides (NDIs) have been disclosed. 23…”

Section: Introductionmentioning

confidence: 99%

Expanding the Scope of Electron-Deficient C–H Building Blocks: Direct Arylation of Pyromellitic Acid Diimide

2017

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Direct C–H activation of pyromellitic diimide (PMDI) is reported for the first time. The method avoids cumbersome pathways involving bromination usually required for further cross-coupling. Good to excellent yields of mono- and di-substituted PMDI derivatives can be obtained under optimized reaction conditions. The reaction scope was also explored, and the materials were characterized with respect to their thermal, optical, and electronic properties.

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“…Methodologies for functionalizing simpler benzothiazole and benzobisthiazole derivatives have been previously developed, , and we recently reported a C–H iodination methodology for electron-withdrawing aromatic systems, including a representative TsCDI and TCDI monomer . In addition, other C–H functionalization strategies have also been developed for similar compounds. − These prior results all indicate the potential for C–H functionalization chemistry to be applied to the synthesis of TsCDI- and TCDI-based materials. Here, we describe the synthesis, C–H functionalization reactivity, and optical and electrochemical properties of TsCDIs and TCDIs and their derivatives.…”

Section: Introductionmentioning

confidence: 90%

Synthesis and C–H Functionalization Chemistry of Thiazole-Semicoronenediimides (TsCDIs) and -Coronenediimides (TCDIs)

et al. 2017

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Coronenediimide (CDI) derivatives have a planar structure, a reasonably high electron affinity, and a rigid and extended delocalized π-system. Therefore, this core and variants thereof may be promising building blocks for the synthesis of electron transport materials. Herein, we have synthesized thiazole-semicoronenediimides (TsCDIs) and -coronenediimides (TCDIs) by a two-step process from a perylenediimide (PDI) precursor. Conditions for C-H arylation and heteroarylation of the thiazole moiety of this core were developed and were successfully used for the synthesis of dimer, triad, and polymeric materials. The optical and electrochemical properties of these materials and their monomers were examined as a function of side-chain modification and π-extension. With their broad optical absorption and low reduction potentials, these materials could be candidates as organic semiconductors for applications in OFETs and as nonfullerene acceptors.

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Direct core functionalisation of naphthalenediimides by iridium catalysed C–H borylation

Cited by 14 publications

References 89 publications

A Decatwistacene with an Overall 170° Torsion

A Decatwistacene with an Overall 170° Torsion

Expanding the Scope of Electron-Deficient C–H Building Blocks: Direct Arylation of Pyromellitic Acid Diimide

Synthesis and C–H Functionalization Chemistry of Thiazole-Semicoronenediimides (TsCDIs) and -Coronenediimides (TCDIs)

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