Nonlinear Polyfused Aromatics with Extended π-Conjugation from Phenanthrotriphenylene, Tetracene, and Pentacene: Syntheses, Crystal Packings, and Properties

Kumar, Sushil; Huang, Ding‐Chi; Venkateswarlu, Samala; Tao, Yu‐Tai

doi:10.1021/acs.joc.8b01582

Cited by 16 publications

(20 citation statements)

References 55 publications

(27 reference statements)

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“…[119] Homodimers of types 130-132 as well as unsymmetric biaryls (e.g. [133][134][135]were obtained in good yields (Figure 9).…”

Section: Palladiummentioning

confidence: 99%

“…Tao and co‐workers have utilized the FeCl 3 /CH 3 NO 2 /CH 2 Cl 2 system for oxidative cyclization reactions in the synthesis of numerous extended planar and curved PAHs . Tetranaphthopentacene 148 is one of many interesting examples prepared by this research group (Figure ) …”

Section: Intramolecular Oxidative Aromatic Couplingmentioning

confidence: 99%

“…[132] Taoa nd co-workers have utilized the FeCl 3 /CH 3 NO 2 / CH 2 Cl 2 system for oxidative cyclization reactions in the synthesis of numerous extended planar and curved PA Hs. [133][134][135][136] Tetranaphthopentacene 148 is one of many interesting examples prepared by this research group ( Figure 10). [135] Roberts,K rische,a nd co-workers have exploited ruthenium-catalyzed diol-diene benzannulation for the construction of various polyphenylene-type PA Hprecursors.…”

Section: Large Planar Pahs Expanded Acenes and Nanographenesmentioning

confidence: 99%

“…[133][134][135][136] Tetranaphthopentacene 148 is one of many interesting examples prepared by this research group ( Figure 10). [135] Roberts,K rische,a nd co-workers have exploited ruthenium-catalyzed diol-diene benzannulation for the construction of various polyphenylene-type PA Hprecursors. [137] Treatment of zigzag-type oligophenylene precursors with FeCl 3 in dichloromethane in the presence of 4 molecular sieves led to the formation of nine new C aryl -C aryl bonds and afforded PA Hs 149 a-d in moderate yields (9-40 %; Figure 10).…”

Section: Large Planar Pahs Expanded Acenes and Nanographenesmentioning

confidence: 99%

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Synthetic Applications of Oxidative Aromatic Coupling—From Biphenols to Nanographenes

et al. 2019

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Oxidative aromatic coupling occupies a fundamental place in the modern chemistry of aromatic compounds. It is a method of choice for the assembly of large and bewildering architectures. Considerable effort was also devoted to applications of the Scholl reaction for the synthesis of chiral biphenols and natural products. The ability to form biaryl linkages without any prefunctionalization provides an efficient pathway to many complex structures. Although the chemistry of this process is only now becoming fully understood, this reaction continues to both fascinate and challenge researchers. This is especially true for heterocoupling, that is, oxidative aromatic coupling with the chemoselective formation of a C−C bond between two different arenes. Analysis of the progress achieved in this field since 2013 reveals that many groups have contributed by pushing the boundary of structural possibilities, expanding into surface‐assisted (cyclo)dehydrogenation, and developing new reagents.

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“…[119] Homodimers of types 130-132 as well as unsymmetric biaryls (e.g. [133][134][135]were obtained in good yields (Figure 9).…”

Section: Palladiummentioning

confidence: 99%

Section: Intramolecular Oxidative Aromatic Couplingmentioning

confidence: 99%

Section: Large Planar Pahs Expanded Acenes and Nanographenesmentioning

confidence: 99%

Section: Large Planar Pahs Expanded Acenes and Nanographenesmentioning

confidence: 99%

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Synthetic Applications of Oxidative Aromatic Coupling—From Biphenols to Nanographenes

et al. 2019

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“…In our previous reports on nitrogen‐incorporated PHs, the phenanthrene‐ and tetracene‐fused carbazoles were obtained from respective polyaryl‐substituted carbazoles via simple Scholl reactions . Similarly, phenanthrotriphenylenes were successfully prepared by performing Scholl reactions on tetraphenylbenzenes (Scheme ) …”

Section: Introductionmentioning

confidence: 99%

Accessing π‐expanded heterocyclics beyond dibenzothiophene: Syntheses and properties of phenanthrothiophenes

Venkateswarlu

Prakoso

Kumar

et al. 2020

J Chinese Chemical Soc

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A series of phenanthrothiophenes are designed and synthesized from polyarylthiophenes through regioselective Scholl reactions in one step using iron chloride as catalyst. The molecular structures of these heteroarenes displayed multiple twisted fjords, which perturb the shapes of the polycyclic frameworks to pack in slipped to near‐perfect face‐to‐face styles in parallel or antiparallel packings. Field‐effect transistor devices using single crystals of 6,12‐difluorodiphenanthro[9, 10‐b:9′, 10′]thiophene gave a hole mobility of 0.22 cm2 V−1 s−1.

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Electrochemical Syntheses of Polycyclic Aromatic Hydrocarbons (PAHs)

2023

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Polycyclic aromatic hydrocarbons (PAHs) have surfaced as increasingly viable components in optoelectronics and material sciences. The development of highly efficient and atom‐economic tools to prepare PAHs under exceedingly mild conditions constitutes a long‐term goal. Traditional syntheses of PAHs have largely relied on multistep approaches or the conventional Scholl reaction. However, Scholl reactions are largely inefficient with electron‐deficient substrates, require stoichiometric chemical oxidants, and typically occur in the presence of strong acid. In sharp contrast, electrochemistry has gained considerable momentum during the past decade as an alternative for the facile and straightforward PAHs assembly, generally via electro‐oxidative dehydrogenative annulation, releasing molecular hydrogen as the sole stoichiometric byproduct by the hydrogen evolution reaction (HER). This review provides an overview on the recent and significant advances in the field of electrochemical syntheses of various PAHs until January 2023.This article is protected by copyright. All rights reserved

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Nonlinear Polyfused Aromatics with Extended π-Conjugation from Phenanthrotriphenylene, Tetracene, and Pentacene: Syntheses, Crystal Packings, and Properties

Cited by 16 publications

References 55 publications

Synthetic Applications of Oxidative Aromatic Coupling—From Biphenols to Nanographenes

Synthetic Applications of Oxidative Aromatic Coupling—From Biphenols to Nanographenes

Accessing π‐expanded heterocyclics beyond dibenzothiophene: Syntheses and properties of phenanthrothiophenes

Electrochemical Syntheses of Polycyclic Aromatic Hydrocarbons (PAHs)

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