<i>ortho O</i>-Annulated azabenzannulated perylenediimide and bisazacoronenediimide

David, Arthur H. G.; Shymon, Daryna; Melville, Hayley; Accou, Lou-Ann; Gapin, Adèle; Allain, Magali; Alévêque, Olivier; Force, Maximilien; Grosjean, Alexis; Hudhomme, Piétrick; Le Bras, Laura; Goujon, Antoine

doi:10.1039/d3tc02376a

Cited by 5 publications

(1 citation statement)

References 96 publications

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“…Blends of this compound with PTB7-Th donor polymer afforded an average PCE of 1.43 %. [57] We Figure 6. Self-assembled PDI cages from a) Ke and Zhang, [46] and b) Coskun and Šolomek.…”

Section: Organic Solar Cells (Oscs)mentioning

confidence: 98%

Dynamic Covalent Synthesis Applied to Optoelectronic and Energy Materials: Design, Applications and Limitations

Chatir,

David,

Gapin

et al. 2024

Eur J Org Chem

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Dynamic Covalent Chemistry, consisting in the use of dynamic covalent bonds (DCBs) to create complex objects by working at the thermodynamic equilibrium, has undeniable advantages for the preparation of conjugated systems with tailored optoelectronic properties for organic electronics. Chemists can combine simple building blocks with simple functional groups of appropriate geometry, structure and stoichiometry to build multidimensional conjugated architectures. Dynamic covalent reactions are often precious metal‐free, generate little to no side products and are very efficient. DCBs however afford sensitive materials, and consequently a balance needs to be found between the ease of synthesis, the stability and the performances. The dynamicity of the target materials hence can considerably reduce their applicability in organic electronics where strongly stable materials are needed, but opens the door to stimuli‐responsive behaviour and recyclability. A way to overcome dynamicity issues is to lock DCBs, but often at the cost of decreased conjugation. In this review, we will highlight how DCBs are employed to prepare functional optoelectronically active materials, such as discrete molecules, polymers or covalent organic frameworks, applied in fields ranging from organic light‐emitting diodes and solar cells to organic batteries and transistors. We will also discuss their limitations, benefits and current challenges to overcome.

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“…Blends of this compound with PTB7-Th donor polymer afforded an average PCE of 1.43 %. [57] We Figure 6. Self-assembled PDI cages from a) Ke and Zhang, [46] and b) Coskun and Šolomek.…”

Section: Organic Solar Cells (Oscs)mentioning

confidence: 98%

Dynamic Covalent Synthesis Applied to Optoelectronic and Energy Materials: Design, Applications and Limitations

Chatir,

David,

Gapin

et al. 2024

Eur J Org Chem

Self Cite

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Intermolecular Anionic Mixed‐Valence and π‐Dimer Complexes of ortho‐Pentannulated Bisazacoronene Diimide

David,

Roger,

Alévêque

et al. 2024

Angewandte Chemie

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This study reports the serendipitous discovery of intermolecular anionic mixed‐valence (MV) and π‐dimer species in ortho‐pentannulated BisAzaCoroneneDiimides (BACDs) during their electrochemical reduction in a non‐aqueous solvent. A library of nitrogen‐containing extended PDIs was synthesized via an aza‐benzannulation reaction followed by a Pd‐catalysed ortho‐pentannulation reaction. Ortho‐pentannulated BACDs revealed strong aggregation abilities in solution. Concentration‐dependent UV‐vis absorption spectra, variable temperature 1H NMR experiments, and atomic force microscopy coupled to molecular dynamics support their self‐assembly into columnar aggregates. Cyclic voltammetry experiments in dichloromethane reveal prominent splitting of the first reduction wave, attributed to the formation of unprecedented intermolecular anionic MV and π‐dimers in organic solvent. These species were thoroughly characterized by real‐time spectroelectrochemistry, electrochemical simulations and theoretical calculations. Remarkably, this work underscores the tuneable nature of AzaBenzannulatedPerylene Diimides (AzaBPDIs) and BACDs, emphasizing their potential as a promising scaffold for designing supramolecular materials with long‐range radical anion delocalization. The observation of this phenomenon provides insights into the fundamental behaviour of supramolecular organic semiconductors, thereby paving the way for the development of novel electronic devices and electron‐deficient materials.

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Intermolecular Anionic Mixed‐Valence and π‐Dimer Complexes of ortho‐Pentannulated Bisazacoronene Diimide

David,

Roger,

Alévêque

et al. 2024

Angew Chem Int Ed

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This study reports the serendipitous discovery of intermolecular anionic mixed‐valence (MV) and π‐dimer species in ortho‐pentannulated BisAzaCoroneneDiimides (BACDs) during their electrochemical reduction in a non‐aqueous solvent. A library of nitrogen‐containing extended PDIs was synthesized via an aza‐benzannulation reaction followed by a Pd‐catalysed ortho‐pentannulation reaction. Ortho‐pentannulated BACDs revealed strong aggregation abilities in solution. Concentration‐dependent UV/Vis absorption spectra, variable temperature 1H NMR experiments, and atomic force microscopy coupled to molecular dynamics support their self‐assembly into columnar aggregates. Cyclic voltammetry experiments in dichloromethane reveal prominent splitting of the first reduction wave, attributed to the formation of unprecedented intermolecular anionic MV and π‐dimers in organic solvent. These species were thoroughly characterized by real‐time spectroelectrochemistry, electrochemical simulations and theoretical calculations. Remarkably, this work underscores the tuneable nature of AzaBenzannulatedPerylene Diimides (AzaBPDIs) and BACDs, emphasizing their potential as a promising scaffold for designing supramolecular materials with long‐range radical anion delocalization. The observation of this phenomenon provides insights into the fundamental behaviour of supramolecular organic semiconductors, thereby paving the way for the development of novel electronic devices and electron‐deficient materials.

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ortho O-Annulated azabenzannulated perylenediimide and bisazacoronenediimide

Abstract: The development of new n-type organic semiconductors is crucial to the development of organic electronics. The introduction of heteroatoms into polycyclic aromatic hydrocarbons (PAHs) or nanographenes has demonstrated to be...

Cited by 5 publications

References 96 publications

Dynamic Covalent Synthesis Applied to Optoelectronic and Energy Materials: Design, Applications and Limitations

Dynamic Covalent Synthesis Applied to Optoelectronic and Energy Materials: Design, Applications and Limitations

Intermolecular Anionic Mixed‐Valence and π‐Dimer Complexes of ortho‐Pentannulated Bisazacoronene Diimide

Intermolecular Anionic Mixed‐Valence and π‐Dimer Complexes of ortho‐Pentannulated Bisazacoronene Diimide

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