Disubstituted 1,6-methano[10]annulene derivatives for use in organic light-emitting diodes

Kajioka, Takanori; Ikai, Masamichi; Fujikawa, Hisayoshi; Taga, Yasunori

doi:10.1016/j.tet.2004.05.050

Cited by 7 publications

(4 citation statements)

References 11 publications

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“…[67] Starting synthetically from a cycloheptatriene, recent work by Kajioka et al prepared hole-transporting triarylamines whose amorphous solidstate properties made them suitable electroluminescent OLED materials. [68] To the best of our knowledge, there are no reports describing the incorporation of the methano [10]annulenes into the backbones of semiconducting organic polymers. …”

Section: A Bigger Benzene: [10]annulenementioning

confidence: 99%

Emerging Prospects for Unusual Aromaticity in Organic Electronic Materials: The Case for Methano[10]annulene

2008

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Section: A Bigger Benzene: [10]annulenementioning

confidence: 99%

Emerging Prospects for Unusual Aromaticity in Organic Electronic Materials: The Case for Methano[10]annulene

2008

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“…Application of these diaryl derivatives with suitable substituents at their phenyl rings to a light-emitting material in organic electroluminescent (EL) devices was reported by researchers at Toyota Central R&D Laboratories [33]. Application of these diaryl derivatives with suitable substituents at their phenyl rings to a light-emitting material in organic electroluminescent (EL) devices was reported by researchers at Toyota Central R&D Laboratories [33].…”

Section: 6-methano[10]annuleno[34-c]thiophenementioning

confidence: 99%

Revisitation of Cycloheptatriene Derivatives as a Building Block for Various Substituted and Fused 1,6-Methano[10]annulenes and Substituted 4,9-Methanothia[11]annulenes

Kuroda¹,

Kajioka²,

Fukuta³

et al. 2007

MROC

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Cl Cl Br Br Br Br 1 6 4 3 2 5 7 8 9 10 11 1 Scheme 1. Vogel's first method of synthesizing 1.Abstract: A synthetic maneuver from 1,6-diacetyl-and 1,6-diformyl-1,3,5-cycloheptatrienes toward various 1,6-methano[10]annulenes, such as diaryl-substituted, cyclobutene-annulated, and thiophene-annulated derivatives and its quinodimethane-type compound, and 4,9-methanothia[11]annulenes is spotlighted based on our recent research efforts. The crystal structure analysis of the annulenes, discussion of mechanistic details of a key cyclization step and application of some annulene derivatives to a material in organic electroluminescent devices are also described.

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“…We initiated our explorations with the methano[10]annulene ring system, a remarkable hydrocarbon whose synthesis was developed by Professor Emanuel Vogel in the mid-1960s [ 7 ]. Although a variety of more complex electronic molecules have been built from this annulene core over the intervening decades [ 8 , 9 , 10 ], we were not aware of any studies to incorporate this 10 pi-electron aromatic molecule into conjugated polymers, either for solution or thin-film solid-state measurements. Larger aromatics such as the 14 pi-electron dihydrodimethylpyrene have been included into conjugated polymers but have not been compared in a side-by-side sense to more classical benzenoid aromatics [ 11 , 12 ].…”

Section: Resultsmentioning

confidence: 99%

Non-Traditional Aromatic Topologies and Biomimetic Assembly Motifs as Components of Functional Pi-Conjugated Oligomers

2010

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This article will highlight our recent work using conjugated oligomers as precursors to electroactive polymer films and self-assembling nanomaterials. One area of investigation has focused on nonbenzenoid aromaticity in the context of charge delocalization in conjugated polymers. In these studies, polymerizable pi-conjugated units were coupled onto unusual aromatic cores such as methano[10]annulene. This article will also show how biologically-inspired assembly of molecularly well-defined oligopeptides that flank pi-conjugated oligomers has resulted in the aqueous construction of 1-dimensional nanomaterials that encourage electronic delocalization among the pi-electron systems.

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Disubstituted 1,6-methano[10]annulene derivatives for use in organic light-emitting diodes

Cited by 7 publications

References 11 publications

Emerging Prospects for Unusual Aromaticity in Organic Electronic Materials: The Case for Methano[10]annulene

Emerging Prospects for Unusual Aromaticity in Organic Electronic Materials: The Case for Methano[10]annulene

Revisitation of Cycloheptatriene Derivatives as a Building Block for Various Substituted and Fused 1,6-Methano[10]annulenes and Substituted 4,9-Methanothia[11]annulenes

Non-Traditional Aromatic Topologies and Biomimetic Assembly Motifs as Components of Functional Pi-Conjugated Oligomers

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