Spiro-fused bis-hexa-<i>peri</i>-hexabenzocoronene

Hu, Yunbin; Wang, Di; Baumgarten, Martin; Schollmeyer, Dieter; Müllen, Kläus; Narita, Akimitsu

doi:10.1039/c8cc07405d

Cited by 27 publications

(16 citation statements)

References 43 publications

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“…[36] Hexa-peri-hexabenzocoronene (HBC), with a pronounced self-assembly and high intrinsic charge-carrier mobility, has been reported by Muellen et al [38] This group has further demonstrated the efficient synthesis of a spiro-fused HBC dimer (compound 35, Scheme 14) with robust orthogonally arranged spiro-linked HBC structures. [39] Noteworthily, adjacent compound 35 molecules are stacked by π-π overlaps of HBC subunits, with intermolecular distances ranging from 3.42 to 3.63 Å ( Figure 5). Compared with its HBC counterpart, compound 35 exhibited a similar but less structured absorption pattern, along with a two-fold enhanced absorption behavior and a marginally redshifted absorption maximum.…”

Section: Other Extensions Of Condensed Spirobifluorenesmentioning

confidence: 99%

Rigidly Fused Spiro‐Conjugated π‐Systems

Xia

Baumgarten

2020

ChemPlusChem

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Spiro‐fused π‐systems have gained considerable attention for their application as semiconductors in molecular electronics. Here, a synopsis regarding recent breakthroughs in ladderized spirobifluorenes and indeno‐spirobifluorenes, along with further spiro‐condensed heteroatomic hydrocarbons with donor‐acceptor moieties, is provided. Additionally, an extended range of rigid spirobifluorene polymers and specific doubly linked spiro‐systems with partial chiral character is discussed. The diverse applications of the aforementioned structures are thoroughly evaluated.

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Section: Other Extensions Of Condensed Spirobifluorenesmentioning

confidence: 99%

Rigidly Fused Spiro‐Conjugated π‐Systems

Xia

Baumgarten

2020

ChemPlusChem

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“…Two main strategies for fabricating molecular NGs, with defined chemical structures, have been developed in recent years. On one hand, oxidative cyclodehydrogenation of custom-made polycyclic aromatic hydrocarbons (PAHs) − and, on the other hand, on-surface cyclodehydrogenation have evolved into powerful and groundbreaking strategies for the preparation of atomically precise molecular NGs. − To this end, the 13 fused-benzene rings of hexa- peri -hexabenzocoronene (HBC), which are arranged in a 2D disk-shaped fashion, render HBCs the smallest graphene fragment. Driven by its tendency to π–π stacking, highly ordered columnar stacks of HBCs have been exploited for several applications. ,− …”

Section: Introductionmentioning

confidence: 99%

Homo and Hetero Molecular 3D Nanographenes Employing a Cyclooctatetraene Scaffold

et al. 2019

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Two novel homo and hetero three-dimensional nanographenes, NG1 and NG2, featuring a cyclooctatetraene core are designed, synthesized, and characterized. A concise and efficient bottom-up methodology was employed during which 24 new carbon−carbon bonds were formed. By means of a Scholl reaction nanographenes with 53 fused rings are realized, which exhibited good solubility in common organic solvents. The resulting saddle-like structures of NG1 and NG2 are electron-rich and show good chemical and electrochemical stability. Their molecular structures are fully elucidated by single-crystal X-ray crystallography. From their crystal structure analysis is concluded that both nanographenes are chiral and crystallize as a racemic mixture. Our work was rounded-off by excited state investigations such as electron and energy transfer with electron-acceptors and -donors.

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“…However, modification of 9,9′‐spirobifluorene has mainly focused on the singly core‐substitution at different reaction positions, and studies that explored extension of the spiro‐π‐systems via annulation, which could increase intermolecular π•••π overlap area by expanded rigid spiroconjugation in the solid state, are rather limited. [ 19–28 ]…”

Section: Figurementioning

confidence: 99%

“…However, modification of 9,9′-spirobifluorene has mainly focused on the singly core-substitution at different reaction positions, and studies that explored extension of the spiro-π-systems via annulation, which could increase intermolecular π•••π overlap area by expanded rigid spiroconjugation in the solid state, are rather limited. [19][20][21][22][23][24][25][26][27][28] Halogenation has been an important chemical modification means applied in constructing various organic semiconductors such as fluorination and chlorination. [29][30] Compared to fluorination that has been well-studied, the chlorination strategy has not been extensively investigated as the larger atomic size of chlorine results in steric effects in conjugated backbones.…”

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confidence: 99%

Chlorinated Spiroconjugated Fused Extended Aromatics for Multifunctional Organic Electronics

et al. 2021

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various hybrid devices have been developed for real-world applications. The preparation process of hybrid devices, however, usually involves vast variety of materials, which not only increases the cost but also makes the process more cumbersome. Thus, there emerges the need to explore multifunctional organic electronic materials to simplify the preparation process and reduce the cost. Spiro-fused polycyclic aromatic compounds, with orthogonal π-subsystems linked by a sp 3-hybridized spiro-atom, have been extensively explored as organic electronic materials due to rigid 3D orthogonal configuration, good processability, excellent thermal and optical stability, and exclusive spiroconjugation effects. [4-7] Spiroconjugation, first described by Simmons and Fukunaga in 1967, refers to the delocalization and bandgap alteration that occurs upon orbital interaction between the π systems of the two spiro-fused planar pieces. [8] The unique 3D rigid spiroconjugation architecture not only reduces intermolecular electronic coupling and in turn the charge recombination but also increases charge transport capability. [9] Notably, 9,9′-spirobifluorene, the most prominent class of The synthesis of a new molecule, SFIC-Cl, is reported, which features enhanced π-electron delocalization by spiroconjugation and narrowed bandgap by chlorination. SFIC-Cl is integrated into a single-crystal transistor (OFET) and organic light-emitting diode (OLED). The material demonstrates remarkable transport abilities across various solution-processed OFETs and retains efficient radiance in a near-infrared OLED emitting light at 700 nm. Furthermore, the intermolecular multi-dimensional connection of SFIC-Cl enables the fabrication of a single-component large-area (2 × 2 cm 2) near-infrared OLED by spin-coating. The SFIC-Cl-acceptor-based solar cell shows excellent power conversion efficiency of 10.16% resulting from the broadened and strong absorption and well-matched energy levels. The study demonstrates that chlorinated spiroconjugated fused systems offer a novel direction toward the development of high-performance organic semiconductor materials for hybrid organic electronic devices.

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Spiro-fused bis-hexa-peri-hexabenzocoronene

Abstract: A spiro-fused hexa-peri-hexabenzocoronene dimer is first prepared, which is confirmed by X-ray crystallography, exhibiting reversible redox property.

Cited by 27 publications

References 43 publications

Rigidly Fused Spiro‐Conjugated π‐Systems

Rigidly Fused Spiro‐Conjugated π‐Systems

Homo and Hetero Molecular 3D Nanographenes Employing a Cyclooctatetraene Scaffold

Chlorinated Spiroconjugated Fused Extended Aromatics for Multifunctional Organic Electronics

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