Carbazole‐Fused Polycyclic Aromatics Enabled by Regioselective Scholl Reactions

Zhao, Mengna; Pun, Sai Ho; Gong, Qi; Miao, Qian

doi:10.1002/ange.202107373

Cited by 7 publications

(4 citation statements)

References 73 publications

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“…During this reaction process, the original structure of the aromatic rings may undergo rearrangement, leading to new structural configurations. [65,117] This can result in product structures different from the expected ones, so such rearrangements are usually to be avoided. However, rearrangement reactions can also be an opportunity to discover new structures.…”

Section: Chiral Twist Of Hexagonal Rings In Nanographenementioning

confidence: 99%

Chiral twisted molecular carbons: Synthesis, properties, and applications

Zhang,

Guan,

Luo

et al. 2024

Interdisciplinary Materials

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In recent years, the precisely controlled synthesis of chiral twisted molecular carbons has emerged as a forefront topic in the research of carbon materials. Molecular carbons refer to carbon nanomaterials synthesized with precision at the atomic level. Through rational design, rigid and stable chiral twisted structures can be synthesized. The exploration in the field of chiral twisted molecular carbons is key to fully understanding the various twisted configurations of carbon materials and delving into the relationship between structure design and functionality. This review explores chiral twisted configurations of carbon nanomaterials such as nanographene, carbon nanobelts, carbon nanosheets, graphdiyne, etc. It emphasizes the role of photocyclization, Scholl reaction, and Diels–Alder reactions in achieving precise chiral control and discusses a range of innovative design strategies. These strategies have led to the development of various twisted structures, such as helical, propeller, and Möbius strip configurations. The introduction of chirality, combined with the inherent exceptional optical properties of nanocarbon materials, has facilitated the creation of materials with superior chiroptical performances. This advancement is driving applications in fields such as optoelectronics and chiral optics.

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Section: Chiral Twist Of Hexagonal Rings In Nanographenementioning

confidence: 99%

Chiral twisted molecular carbons: Synthesis, properties, and applications

Zhang,

Guan,

Luo

et al. 2024

Interdisciplinary Materials

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“…In addition, incorporating heteroatoms such as N, O, and S into cycloarenes leads to heterocycloarenes, which can be identified as the isoelectronic species of their all-carbon analogues but may display enhanced stability, as well as impart different molecular geometries and electronic properties. In 1997, Demeunynck and co-workers reported the first successful and conclusive synthesis of a nitrogen-containing unsubstituted heterocycloarene (N-kekulene, Figure a) with a planar shape accompanied by poor solubility .…”

Section: Introductionmentioning

confidence: 99%

“…In 1997, Demeunynck and co-workers reported the first successful and conclusive synthesis of a nitrogen-containing unsubstituted heterocycloarene (N-kekulene, Figure a) with a planar shape accompanied by poor solubility . In 2018, Miao and co-workers developed a sulfur-containing alkoxyl-substituted heterocycloarene with a saddle shape for organic field-effect transistors (OFETs), which produced a hole mobility of 2.7 × 10 –4 cm 2 V –1 s –1 . This low mobility is attributable to the curved backbone structure that results in the amorphous nature of the film.…”

Section: Introductionmentioning

confidence: 99%

“…This low mobility is attributable to the curved backbone structure that results in the amorphous nature of the film. Despite a lot of synthetic efforts being made on (hetero)cycloarene chemistry that lead to a variety of homologues, isoelectronic species, and derivatives, , their field-effect transistor applications have been rarely explored, , presumably as a result of the lack of capability to tailor the molecular structure and manipulate the molecular packing in the aggregate states.…”

Section: Introductionmentioning

confidence: 99%

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Alkyl-Substituted N,S-Embedded Heterocycloarenes with a Planar Aromatic Configuration for Hosting Fullerenes and Organic Field-Effect Transistors

Zhang

Yang

et al. 2022

J. Am. Chem. Soc.

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Cycloarenes and heterocycloarenes display unique physical structures and hold great potential as organic semiconductors. However, the synthesis of (hetero)cycloarenes remains a big challenge, and there are limited reports on their applications. Herein, a series of nitrogen- and sulfur-codoped cycloarenes NS-Octulene-n (n = 2, 3, 4) with branched alkyl substituents containing linear spacer groups from C2 to C4 have been conveniently synthesized. Compared with their isoelectronic analogues Octulene and S-Octulene, both having a saddle-shaped configuration, the coincorporation of two nitrogen atoms and two sulfur atoms leads to a fully coplanar aromatic backbone structure. Each of these three planar heterocycloarenes acts as a supramolecular host for encapsulation of both fullerenes C60 and C70 with a stronger donor–acceptor interaction for the complexation between the heterocycloarene and C70 due to the unique molecular geometry and defined cavity. Meanwhile, the electron-rich nitrogen atoms also slightly increase the energies of both highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) in this series of planar heterocycloarenes, indicating that they can be used as p-type semiconductors. Most importantly, benefitting from the planar π-conjugated backbone structure accompanied by excellent crystallinity and ordered molecular packing, as well as upon the engineering of the alkyl chain branching position, thin-film field-effect transistors of NS-Octulene-3 with moderate alkyl branching point exhibit the maximum hole mobility of 0.86 cm2 V–1 s–1, which is the highest for (hetero)cycloarene-based organic semiconductors. This study will shed new light on designing novel high-performance macrocyclic polycyclic aromatic hydrocarbon (PAH) semiconductors.

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A Near‐Infrared Absorbing and Emissive Quadruple Helicene Enabled by the Scholl Reaction of Perylene

et al. 2022

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Herein, we report the synthesis, structural analysis, optical and chiroptical properties of a novel quadruple helicene, which has two [6] and two [7]helicene moieties fused in a contorted framework of 92 sp2 carbon atoms. It was synthesized by the Scholl reaction of a perylene‐containing substrate with the formation of eight carbon‐carbon bonds on the perylene unit in a single synthetic operation. Chemical oxidation of the quadruple helicene with tris(4‐bromophenyl)ammoniumyl hexachloroantimonate resulted in an air‐stable dication, which exhibits the same helicity in its four helicene moieties as unambiguously identified by single‐crystal X‐ray crystallography. The quadruple helicene exhibits unusual near‐infrared absorption and emission with absorption and emission maxima at 848 nm and 977 nm, respectively, and its isolated enantiomers exhibit electronic circular dichroism in the near‐infrared and visible‐light regions.

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Carbazole‐Fused Polycyclic Aromatics Enabled by Regioselective Scholl Reactions

Cited by 7 publications

References 73 publications

Chiral twisted molecular carbons: Synthesis, properties, and applications

Chiral twisted molecular carbons: Synthesis, properties, and applications

Alkyl-Substituted N,S-Embedded Heterocycloarenes with a Planar Aromatic Configuration for Hosting Fullerenes and Organic Field-Effect Transistors

A Near‐Infrared Absorbing and Emissive Quadruple Helicene Enabled by the Scholl Reaction of Perylene

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