1,5,9-Triaza-2,6,10-triphenylboracoronene: BN-Embedded Analogue of Coronene

Li, Gang; Xiong, Wei‐Wei; Gu, Peiyang; Cao, Jun; Zhu, Jia; Ganguly, Rakesh; Li, Yongxin; Grimsdale, Andrew C.; Zhang, Qichun

doi:10.1021/ol503575t

Cited by 80 publications

(47 citation statements)

References 31 publications

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“…The molecules showed a tendency to pack into a columnar structure, which facilitated the formation of one-dimensional micro-ribbons through solution-processed selfassembly. 183 In the same year, Bettinger et al successfully constructed B 3 N 3 -doped p-HBC 81 by thermolysis of a tris(2-biphenylyl)borazine precursor at 550 1C. Photoconductive properties were also observed, indicating the potential application (Fig.…”

Section: Heteroatom-doped Graphene Moleculesmentioning

confidence: 97%

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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: Heteroatom-doped Graphene Moleculesmentioning

confidence: 97%

“…14). 182,183 The planar and aromatic structure of 80 was clearly revealed by the single-crystal X-ray analysis and NMR spectroscopy. The introduction of BN units in the skeleton had a pronounced influence on its electronic properties and molecular geometry.…”

Section: Heteroatom-doped Graphene Moleculesmentioning

confidence: 99%

New advances in nanographene chemistry

et al. 2015

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“…[23] To our knowledge, this work describes the best example of full ordered BN-doped graphene sheets. At the molecular level, several synthetic methods allowed the preparation of a large number of BN-doped aromatic derivatives, [24][25][26] from azaborines [27] to extended polycyclic aromatic hydrocarbons. In particular, BN-doped naphthalenes, anthracenes, or phenanthrenes could be prepared by diverse synthetic strategies, including AlCl 3 -promoted electrophilic borylation method of arylamines, [28] cyclization-dehydrogenation procedures, [29] or via chelation of bis-borabiphenyl precursors with pyridazine derivatives.…”

Section: Bn-doped Carbon Nanostructuresmentioning

confidence: 99%

“…[30] For example, Nakamura and co-workers described in 2011 a renewed strategy for the synthesis of BN-doped frameworks, [31] via tandem intramolecular electrophilic arene borylation. As a proof of concept, Zhang [25] and Pei [26] simultaneously developed the synthesis of a BN-embedded coronene-type molecule.…”

Section: Bn-doped Carbon Nanostructuresmentioning

confidence: 99%

Renaissance of an Old Topic: From Borazines to BN-doped Nanographenes

Lorenzo-Garcia

Bonifazi

2017

Chimia

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Graphene is one of the leading materials in today's science, but the lack of a band gap limits its application to replace semiconductors in optoelectronic devices. To overcome this limitation, the replacement of C=C bonds by isostructural and isoelectronic bonds is emerging as an effective strategy to open a band gap in monoatomic graphene layers. First prepared by Stock and Pohland in 1926, borazine is the isoelectronic and isostructural inorganic analogue of benzene, where the C=C bonds are replaced by B-N couples. The strong polarity of the BN bonds widens the molecular HOMO-LUMO gap, imparting strong UV-emission/absorption and electrical insulating properties. These properties make borazine a valuable molecular scaffold to be inserted as doping units in graphitic-based carbon materials to tailor a relevant band gap. It is with this objective that we became interested in the development of new synthetic organic methodologies to gain access to functionalized borazine derivatives. In particular, we have described the synthesis of borazine derivatives that, featuring aryl substituents at the B-centers bearing ortho-functionalities, are exceptionally stable against hydrolysis. Building on these structural motifs, we prepared hybrid BN-doped polyphenylene nanostructures featuring controlled doping patterns, both as dosage and orientation. Finally, exploiting the Friedel-Craft electrophilic aromatic substitution, we could develop the first rational synthesis of the first soluble hexa-peri-hexabenzoborazinocoronene and measured its optoelectronic properties, showing a widening of its gap compared to its full-carbon congener.

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“…the changes in UV/Vis absorption or HOMO/ LUMO position) and the arrangement of conjugated frame-works through hydrogen bonding and p-p stacking have been emphasized by several groups. [24][25][26][27][28][29][30][31][32][33] Currently, the advancement on developing n-type (electrontransporting) organic semiconductors is much slower compar-ing with the research of p-type (hole-transporting) ones, which is mainly due to the presence of air and moisture as well as the oxygen-trapping problem. [34] Such issues have become an urgent topic that requires scientists to input their more efforts to address.…”

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confidence: 99%

Photooxidation of a Twisted Isoquinolinone

Zhao

Yang

et al. 2018

Chemistry An Asian Journal

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Understanding the oxidation mechanism and positions of twistacenes and twistheteroacenes under ambient conditions is very important because such knowledge can guide us to design and synthesize novel, larger stable analogues. Herein, we demonstrated for the first time that a twisted isoquinolinone can decompose under oxygen and light at room temperature. The as-decomposed product 1 was fully characterized through conventional methods as well as single-crystal structure analysis. Moreover, the physical properties of the as-obtained product were carefully investigated and the possible formation mechanism was proposed.

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1,5,9-Triaza-2,6,10-triphenylboracoronene: BN-Embedded Analogue of Coronene

Cited by 80 publications

References 31 publications

New advances in nanographene chemistry

New advances in nanographene chemistry

Renaissance of an Old Topic: From Borazines to BN-doped Nanographenes

Photooxidation of a Twisted Isoquinolinone

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