Dibenzodiazapyracylenes: Doubly N‐Doped Cyclopenta‐Fused Polycyclic Molecules That Exhibit High Carrier Mobility

Morimoto, Yuki; Koo, Yu-Jin; Otsubo, Kenji; Kitakado, Hidetsugu; Seki, Shu; Osuka, Atsuhiro; Tanaka, Takayuki

doi:10.1002/anie.202200341

Cited by 10 publications

(2 citation statements)

References 70 publications

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“…Recently, the group of Seki and Tanaka has reported the synthesis and properties of hydrazine embedded benzannulated pyracylenes 128a,b, which were obtained by oxidative N-N linking reaction of cyclophane type precursors 126a,b using potassium tert-butoxide under aerial conditions. 57 The reaction also provided a side-product 127, in which the N-C bond formation took place associated with quenching reaction with oxygen or water. Diazapyracylene 128a displayed a well ordered π-stacking structure with high carrier mobility in the solid state.…”

Section: Scheme 9 the Synthesis Of Sumanenementioning

confidence: 99%

Non-Planar Polycyclic Aromatic Molecules Including Heterole Units

Tanaka¹,

Kise²

2022

HETEROCYCLES

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Recent developments in non-planar polycyclic aromatic molecules bearing heterole units have been reviewed, including internally and externally heteroatom doped corannulenes, rim and benzylic heteroatom doped sumanenes, hexapyrrolohexaazacoronenes, and hetero[n]circulenes. CONTENTS 1. Introduction 2. Heteroatom doped corannulenes 2-1. Internally heteroatom doped corannulenes 2-2. Externally heteroatom doped corannulenes 3. Heteroatom doped sumanenes 3-1. Rim heteroatom doped sumanenes 3-2. Benzylic heteroatom doped sumanenes 4. Other heteroatom doped bowl shaped PAHs

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Section: Scheme 9 the Synthesis Of Sumanenementioning

confidence: 99%

Non-Planar Polycyclic Aromatic Molecules Including Heterole Units

Tanaka¹,

Kise²

2022

HETEROCYCLES

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“…Besides dibenzo-annulated dibenzopyracylene, until recently, further π-expansion of this scaffold has been only sparsely explored. [9][10][11][12] Recently, our group published a boat-shaped hexa-perihexabenzocoronene-pyracylene hybrid (HPH) with multistage redox properties. [13] Motivated by these findings we envisioned that incorporation of a π-conjugated 7-membered ring into the polycyclic scaffold might allow unique modulation of its electronic properties and induction of negative curvature.…”

Section: Introductionmentioning

confidence: 99%

A Negatively Curved π‐Expanded Pyracylene Comprising a Tropylium Cation

Borstelmann,

Bergner,

Rominger

et al. 2023

Angew Chem Int Ed

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We disclose π‐expanded pyracylenes and their cationic species comprising 7‐membered rings. The compounds were synthesized by stepwise oxidative cyclodehydrogenation to monitor the effect of successive cyclization on the structural and optoelectronic properties. As shown by X‐ray crystallography the complete cyclization leads to a boat‐shaped scaffold featuring negative curvature provided by the 7‐membered ring. The embedded tropone unit enabled the convenient generation of a stabilized tropylium cation, showing bathochromically shifted absorption bands reaching into the near‐infrared region beyond 1000 nm. The altered structural features supported by theoretical calculations point towards aromatic character of the positively charged 7‐membered ring.

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High Electron Mobility Hot‐Exciton Induced Delayed Fluorescent Organic Semiconductors

et al. 2023

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The development of high mobility emissive organic semiconductors is of great significance for the fabrication of miniaturized optoelectronic devices, such as organic light emitting transistors. However, great challenge exists in designing key materials, especially those who integrates triplet exciton utilization ability. Herein, dinaphthylanthracene diimides (DNADIs), with 2,6‐extended anthracene donor, and 3′‐ or 4′‐substituted naphthalene monoimide acceptors were designed and synthesized. By introducing acceptor‐donor‐acceptor structure, both materials show high electron mobility. Moreover, by fine‐tuning of substitution sites, good integration with high solid state photoluminescence quantum yield of 26 %, high electron mobility of 0.02 cm2 V−1 s−1, and the feature of hot‐exciton induced delayed fluorescence were obtained in 4′‐DNADI. This work opens a new avenue for developing high electron mobility emissive organic semiconductors with efficient utilization of triplet excitons.

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Dibenzodiazapyracylenes: Doubly N‐Doped Cyclopenta‐Fused Polycyclic Molecules That Exhibit High Carrier Mobility

Cited by 10 publications

References 70 publications

Non-Planar Polycyclic Aromatic Molecules Including Heterole Units

Non-Planar Polycyclic Aromatic Molecules Including Heterole Units

A Negatively Curved π‐Expanded Pyracylene Comprising a Tropylium Cation

High Electron Mobility Hot‐Exciton Induced Delayed Fluorescent Organic Semiconductors

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