Oxygen‐Doped Zig‐Zag Molecular Ribbons

Berezin, Andrey A.; Biot, Nicolas; Battisti, Tommaso; Bonifazi, Davide

doi:10.1002/anie.201803282

Cited by 36 publications

(30 citation statements)

References 51 publications

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“…The heteroatoms in the nanographene framework provide more opportunities for materials development (i) by modulating the band gap and thus the photophysical properties, (ii) by offering rich electrochemical activities, (iii) by installing coordinating sites for metals, and (iv) by stabilizing charges and spins in the carbon skeleton. 16 Nevertheless, large nanographene molecules and GNRs incorporating various heteroatoms (e.g., B, 17 N, 18,19 O, 20 S, 21 and P 22 ) are still scarce. 16…”

Section: Introductionmentioning

confidence: 99%

Heteroatom-Doped Nanographenes with Structural Precision

et al. 2019

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ConspectusNanographenes, which are defined as nanoscale (1–100 nm) graphene cutouts, include quasi-one-dimensional graphene nanoribbons (GNRs) and quasi-zero-dimensional graphene quantum dots (GQDs). Polycyclic aromatic hydrocarbons (PAHs) larger than 1 nm can be viewed as GQDs with atomically precise molecular structures and can thus be termed nanographene molecules. As a result of quantum confinement, nanographenes are promising for next-generation semiconductor applications with finite band gaps, a significant advantage compared with gapless two-dimensional graphene. Similar to the atomic doping strategy in inorganic semiconductors, incorporation of heteroatoms into nanographenes is a viable way to tune their optical, electronic, catalytic, and magnetic properties. Such properties are highly dependent not only on the molecular size and edge structure but also on the heteroatom type, doping position, and concentration. Therefore, reliable synthetic methods are required to precisely control these structural features. In this regard, bottom-up organic synthesis provides an indispensable way to achieve structurally well-defined heteroatom-doped nanographenes.Polycyclic heteroaromatic compounds have attracted great attention of organic chemists for decades. Research in this direction has been further promoted by modern interest in supramolecular chemistry and organic electronics. The rise of graphene in the 21st century has endowed large polycyclic heteroaromatic compounds with a new role as model systems for heteroatom-doped graphene. Heteroatom-doped nanographene molecules are in their own right promising materials for photonic, optoelectronic, and spintronic applications because of the extended π conjugation. Despite the significant advances in polycyclic heteroaromatic compounds, heteroatom-doped nanographene molecules with sizes of over 1 nm and their relevant GNRs are still scarce.In this Account, we describe the synthesis and properties of large heteroatom-doped nanographenes, mainly summarizing relevant advances in our group in the past decade. We first present several examples of heteroatom doping based on the prototypical nanographene molecule, i.e., hexa-peri-hexabenzocoronene (HBC), including nitrogen-doped HBC analogues by formal replacement of benzene with other heterocycles (e.g., aromatic pyrimidine and pyrrole and antiaromatic pyrazine) and sulfur-doped nanographene molecules via thiophene annulation. We then introduce heteroatom-doped zigzag edges and a variety of zigzag-edged nanographene molecules incorporating nitrogen, boron, and oxygen atoms. We finally summarize heteroatom-doped GNRs based on the success in the molecular cases. We hope that this Account will further stimulate the synthesis and applications of heteroatom-doped nanographenes with a combined effort from different disciplines.

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Section: Introductionmentioning

confidence: 99%

Heteroatom-Doped Nanographenes with Structural Precision

et al. 2019

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“…S5 † shows the calculated HOMO and LUMO orbitals of TTCTTC and TTTCTTTC. It is clear that the HOMO orbitals are mainly distributed on the central chromeno [6,5,4-def]chromene cores for both molecules, while their LUMO orbitals are evenly distributed across the whole conjugated backbone. Therefore, the resultant excited states of the two molecules exhibit charge transfer features from the central conjugated core to the fusedthiophenes.…”

Section: Resultsmentioning

confidence: 99%

“…4 Extended O-doped polycyclic aromatic hydrocarbons and molecular ribbons have been synthesized by Bonifazi and coworkers. 5 You and coworkers have recently devised a [4 + 2] synthetic strategy 6 to synthesize O-containing porphyrins and investigated their absorption and electrochemical properties. 7 Formal pyran units have also been incorporated into conjugated molecules with radical character.…”

Section: Introductionmentioning

confidence: 99%

New fused conjugated molecules with fused thiophene and pyran units for organic electronic materials

et al. 2020

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“…53 In-depth photophysical and electrochemical studies revealed that all pyranopyran derivatives feature strong electron-donating properties due to their high-lying energy HOMO levels. 52,53 In particular, PXX, PXXMI, and PXXDI revealed to be strong photoreducers, with PXX featuring the same photoreducing potential as that of the commonly used Ir(III) complexes. 53a…”

Section: Short Review Syn Thesismentioning

confidence: 98%

“…37 Scheme 15 Proposed formation mechanism for PXX by Weinert and co-workers 47 Building on the Cu-based protocols, our group could achieve the synthesis of extended PXX derivatives. In particular, O-doped armchair 56, 57 49 and zig-zag 58 52…”

Section: Peri-xanthenoxanthene (Pxx)mentioning

confidence: 99%

O-Annulation Leading to Five-, Six-, and Seven-Membered Cyclic Diaryl Ethers Involving C–H Cleavage

Rossignon

Bonifazi

2019

Synthesis

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Cyclic diaryl ethers are present in multiple natural compounds, organic pollutants as well as in π-conjugated organic molecular materials. This short review aims at overviewing the main synthetic advances in the O-annulation methods for preparing five-, six-, and seven-membered rings through C–H cleavage.1 Introduction2 Five-Membered Rings: The Dibenzofuran (DBF) Motif2.1 Palladium-Catalysed C–H Activation2.2 Copper-Catalysed C–H Activation2.3 Non-CH Activation Oxidant-Mediated Cyclisation2.4 Light-Mediated Cyclisation2.5 Acid-catalysed C–O Cleavage/C–O Formation3 Six-Membered Rings: DBX, PXX, Xanthone, and Their Derivatives3.1 Dibenzoxanthene (DBX)3.2 Peri-Xanthenoxanthene (PXX)3.3 Xanthones3.4 Miscellaneous4 Seven-Membered Rings: Cularine5 Conclusion

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Oxygen‐Doped Zig‐Zag Molecular Ribbons

Cited by 36 publications

References 51 publications

Heteroatom-Doped Nanographenes with Structural Precision

Heteroatom-Doped Nanographenes with Structural Precision

New fused conjugated molecules with fused thiophene and pyran units for organic electronic materials

O-Annulation Leading to Five-, Six-, and Seven-Membered Cyclic Diaryl Ethers Involving C–H Cleavage

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