Functionalized Coronenes: Synthesis, Solid Structure, and Properties

Wu, Di; Zhang, Hua; Liang, Jieying; Ge, Haojie; Wu, Jishan; Liu, Sheng Hua; Yin, Jun

doi:10.1021/jo302093t

Cited by 36 publications

(31 citation statements)

References 51 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The ring-closure step involved the efficient construction of two B-N bonds and four B-C bonds through an electrophilic borylation method. The UV-Vis absorption and emission spectra of 80 showed blue-shifted peaks compared to those of a similarly alkoxylated coronene, 184 demonstrating an increase of the energy gap as a result of the BN doping. The molecules showed a tendency to pack into a columnar structure, which facilitated the formation of one-dimensional micro-ribbons through solution-processed selfassembly.…”

Section: Heteroatom-doped Graphene Moleculesmentioning

confidence: 95%

New advances in nanographene chemistry

et al. 2015

View full text Add to dashboard Cite

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.

show abstract

Section: Heteroatom-doped Graphene Moleculesmentioning

confidence: 95%

New advances in nanographene chemistry

et al. 2015

View full text Add to dashboard Cite

show abstract

“…Conversely, the coronene counterpart of compound 1a ( Figure S16) emits in the UV region (λ max = 375 nm) with a much lower quantum yield (Φ f = 0.098 in chloroform). 15 The effects of incorporating B−N units into the π-conjugated core of coronene were further investigated by density functional theory (DFT) calculations ( Figure S17). The molecular geometries of compound 1 and the carbon analogue were optimized using density functional theory (DFT) at the B3LYP/6-31G* level.…”

mentioning

confidence: 99%

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

Xiong

et al. 2015

Org. Lett.

View full text Add to dashboard Cite

A novel BN-fused coronene derivative 1,5,9-triaza-2,6,10-triphenylboracoronene (1) has been successfully synthesized in one step from 2,3,6,7,9,10-hexamethoxy-1,5,9-triamino-triphenylene. Compound 1 has been investigated using photophysical, electrochemical, and molecular simulation methods. Interestingly, three phenyl groups at B centers in compound 1 can be replaced by hydroxyl units stepwise through hydroxylation in wet organic solvents, leading to changes in the packing and physical properties.

show abstract

“…88 This scheme also presents an example of PAH modification using ring closure of an ethynyl unit attached to a bay area (Scheme 4B). 89 Depending on the topology of the twisted oligophenylenes and oligoarylenes, six-membered ring formation has also been accomplished by Friedel-Crafts reactions, as exemplified by the synthesis of 25 (Scheme 4C In the meantime, HBC and its oligomers have found widespread use as building blocks to synthesize various NGs, and this manifold of hydrocarbons includes nonplanar and chiral structures. [91][92][93][94] A full account of this rich chemistry is however beyond the scope of this text.…”

Section: Solution Synthesismentioning

confidence: 99%