Unexpected Phenyl Group Rearrangement during an Intramolecular Scholl Reaction Leading to an Alkoxy-Substituted Hexa-<i>peri</i>-hexabenzocoronene

Dou, Xiaohui; Yang, Xuan; Bodwell, Graham J.; Wagner, Manfred; Enkelmann, Volker; Müllen, Kläus

doi:10.1021/ol0708018

Cited by 116 publications

(62 citation statements)

References 24 publications

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“…1). 78 Nevertheless, the scopes of these synthetic methods have been limited by several factors, including incomplete ''graphitization,'' 79 chlorination 74 and unexpected structural rearrangements [80][81][82][83] during the Scholl reaction. Large oligophenylene precursors have conventionally been prepared through cyclotrimerization of diphenylacetylene derivatives or through a combination of substitution and metalcatalysed coupling reactions as well as Diels-Alder cycloaddition of alkyne and tetraphenylcyclopentadienone derivatives.…”

Section: Synthesis Of Graphene Moleculesmentioning

confidence: 99%

New advances in nanographene chemistry

et al. 2015

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Nanographenes, or extended polycyclic aromatic hydrocarbons, have been attracting renewed and more widespread attention since the first experimental demonstration of graphene in 2004. However, the atomically precise fabrication of nanographenes has thus far been achieved only through synthetic organic chemistry. The precise synthesis of quasi-zero-dimensional nanographenes, i.e. graphene molecules, has witnessed rapid developments over the past few years, and these developments can be summarized in four categories: (1) non-conventional methods, (2) structures incorporating seven- or eight-membered rings, (3) selective heteroatom doping, and (4) direct edge functionalization. On the other hand, one-dimensional extension of the graphene molecules leads to the formation of graphene nanoribbons (GNRs) with high aspect ratios. The synthesis of structurally well-defined GNRs has been achieved by extending nanographene synthesis to longitudinally extended polymeric systems. Access to GNRs thus becomes possible through the solution-mediated or surface-assisted cyclodehydrogenation, or "graphitization," of tailor-made polyphenylene precursors. In this review, we describe recent progress in the "bottom-up" chemical syntheses of structurally well-defined nanographenes, namely graphene molecules and GNRs.

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Section: Synthesis Of Graphene Moleculesmentioning

confidence: 99%

New advances in nanographene chemistry

et al. 2015

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“…did not lead to aryl-aryl couplings. 22 A different behaviour was observed with tetrahydroisoquinoline 44, which could be applied as a starting material in the synthesis of the alkaloid kresigine (45). There, FeCl 3 (6 eq., anhydrous) in dichloromethane was used for promoting the intramolecular formation of the new C-C-bond (Scheme 11).…”

Section: Introductionmentioning

confidence: 99%

Iron(iii) chloride in oxidative C–C coupling reactions

2009

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In this critical review, the use of iron(III) chloride in oxidative C-C couplings of arenes and related unsaturated compounds is presented and reviewed. The approach allows highly selective dimerisations of phenol derivatives, naphthols, and heterocyclic compounds. Sequential couplings give access to structurally well-defined oligo- and polymers. Iron(III) chloride is commercially available and inexpensive. Being a mild oxidising agent it has been applied in numerous reactions leading to new carbon-carbon-bonds in complex molecular arrays (107 references).

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“…Moreover, some particular target compounds were only obtainable from specifically designed isomeric precursors. For example, attempts to prepare alkoxy-functionalized HBCs from the corresponding HPB via oxidative cyclization with FeCl 3 led to variable results with byproducts from alkoxy migrations [31], quinine [32], or indeno fluorene [13,18] formation. However, a hexakis-alkoxy-HBC was accessible from a 1,3,5-tris(biphenyl)benzene derivative 3 [18] or when a phenyl linker is incorporated (Scheme 1, route 4) [33][34][35][36].…”

Section: Synthesis Of Hbc and Its Derivativesmentioning

confidence: 99%

“…A stepwise cyclization mechanism has been suggested for HBC formation as semifused HPB derivatives were sometimes isolated as byproducts [8,35]. Two disputed mechanisms for the Scholl reaction have been proposed and investigated: the arenium-ion or radical-cation pathways (Scheme 2) [24,31,[43][44][45][46]. The former (Scheme 2, pathway A) proceeds by protonation of the aromatic precursor, resulting in a σ complex or arenium cation 2(i).…”

Section: Synthesis Of Hbc and Its Derivativesmentioning

confidence: 99%

Hexa-peri-hexabenzocoronene in organic electronics

Seyler

Purushothaman

Jones

et al. 2012

Pure and Applied Chemistry

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Polycyclic aromatic hydrocarbons (PAHs) are in a class of functional organic compounds with increasing importance in organic electronics. Their tunable photophysical properties and typically strong intermolecular associations make them ideal materials in applications where control of charge mobility is essential. Hexa-peri-hexabenzocoronene (HBC) is a disc-shaped PAH that self-associates into columnar stacks through strong π-π interactions. By decorating the periphery of the HBC molecule with various substituents, a range of properties and functions can be obtained including solution processability, liquid crystallinity, and semiconductivity. In this review article, the synthesis, properties, and functions of HBC derivatives are presented with focus on work published in the last five years.

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Unexpected Phenyl Group Rearrangement during an Intramolecular Scholl Reaction Leading to an Alkoxy-Substituted Hexa-peri-hexabenzocoronene

Abstract: A simple dimethoxy-substituted hexa-peri-hexabenzocoronene (m-dimethoxy HBC) was unexpectedly obtained along with a bis-spirocyclic dienone during an intramolecular Scholl reaction of its para isomer.

Cited by 116 publications

References 24 publications

New advances in nanographene chemistry

New advances in nanographene chemistry

Iron(iii) chloride in oxidative C–C coupling reactions

Hexa-peri-hexabenzocoronene in organic electronics

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