The design, synthesis and application of rubicene based polycyclic aromatic hydrocarbons (PAHs)

Ma, Liangzhuo; Han, Yinghui; Shi, Qinqin; Huang, Hui

doi:10.1039/d3tc02876c

J. Mater. Chem. C

2023

DOI: 10.1039/d3tc02876c

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The design, synthesis and application of rubicene based polycyclic aromatic hydrocarbons (PAHs)

Liangzhuo Ma,

Yinghui Han,

Qinqin Shi

et al.

Abstract: Rubicene, a key nanofragment of C70, is attracting great attentions owing to its unique molecular structure and physicochemical properties. As an indeno-annelated polycyclic aromatic hydrocarbon (indeno-PAH), rubicene itself has a...

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Cited by 6 publications

References 61 publications

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Synthesis and Properties of Azadibenzo[a,e]pyrenes

Khomutetckaia,

Ehlers,

Villinger

et al. 2024

Eur J Org Chem

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Four different isomeric azadibenzo[a,e]pyrenes (benzo[4,10]anthra[9,1‐gh]isoquinolines and benzo[4,10]anthra[1,9‐fg]isoquinolines) were prepared by combination of Pd‐catalyzed Sonogashira and Suzuki cross‐coupling, Brønsted acid mediated cycloisomerization and Pd‐catalysed CH‐activation reactions. The optical properties have been studied by steady‐state absorption and emission spectroscopy in different solvents and during acid titration. Trifluoroacetic acid protonation strongly affects absorption and emission properties, with variations depending on the position of the nitrogen atom of the specific compound. Electrochemical analysis showed distinct oxidation and reduction potentials. DFT calculations provided further insights into electronic properties.

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Synthesis and Properties of Azadibenzo[a,e]pyrenes

Khomutetckaia,

Ehlers,

Villinger

et al. 2024

Eur J Org Chem

View full text Add to dashboard Cite

show abstract

Palladium-Catalyzed Double Decarboxylative [3 + 2] Annulation of Naphthalic Anhydrides with Internal Alkynes

Kanganavaree,

Kantarod,

Worakul

et al. 2024

J. Org. Chem.

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A palladium-catalyzed [3 + 2] annulation of naphthalic anhydrides with internal alkynes has been developed. The present protocol offers an efficient and convenient route to access a series of 1,2-disubstituted acenaphthylenes with excellent functional group compatibility. The reaction is proposed to proceed through a double decarboxylation sequence. The reported synthetic protocols can be extended to napthalene- and perylenedicarboximide-containing substrates. The molecular structures, photophysical properties, and frontier molecular orbitals of the obtained adducts were investigated by X-ray crystallography, UV–vis and fluorescence spectroscopy, and DFT calculations.

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Construction of acenaphthylenes via C−H activation-based tandem penta- and hexaannulation reactions

Li,

Liu,

Liu

et al. 2024

Nat Commun

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The design, synthesis and application of rubicene based polycyclic aromatic hydrocarbons (PAHs)

Abstract: Rubicene, a key nanofragment of C70, is attracting great attentions owing to its unique molecular structure and physicochemical properties. As an indeno-annelated polycyclic aromatic hydrocarbon (indeno-PAH), rubicene itself has a...

Cited by 6 publications

References 61 publications

Synthesis and Properties of Azadibenzo[a,e]pyrenes

Synthesis and Properties of Azadibenzo[a,e]pyrenes

Palladium-Catalyzed Double Decarboxylative [3 + 2] Annulation of Naphthalic Anhydrides with Internal Alkynes

Construction of acenaphthylenes via C−H activation-based tandem penta- and hexaannulation reactions

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