Construction of hexabenzocoronene-based chiral nanographenes

Li, Ranran; Wang, Di; Li, Shengtao; An, Peng

doi:10.3762/bjoc.19.54

Beilstein J. Org. Chem.

2023

DOI: 10.3762/bjoc.19.54

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Construction of hexabenzocoronene-based chiral nanographenes

Ranran Li¹,

Di Wang²,

Shengtao Li³

et al.

Abstract: The past decade witnessed remarkable success in synthetic molecular nanographenes. Encouraged by the widespread application of chiral nanomaterials, the design, and construction of chiral nanographenes is a hot topic recently. As a classic nanographene unit, hexa-peri-hexabenzocoronene generally serves as the building block for nanographene synthesis. This review summarizes the representative examples of hexa-peri-hexabenzocoronene-based chiral nanographenes.

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Cited by 11 publications

References 60 publications

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Tetrahedraphene: A Csp³‐centered 3D Molecular Nanographene Showing Aggregation‐Induced Emission

Oró,

Romeo‐Gella,

Perles

et al. 2023

Angewandte Chemie

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The bottom‐up synthesis of 3D tetrakis(hexa‐peri‐hexabenzocoronenyl)methane, “tetrahedraphene”, is reported. This molecular nanographene constituted by four hexa‐peri‐hexabenzocoronene (HBC) units attached to a central sp3 carbon atom, shows a highly symmetric arrangement of the HBC units disposed in the apex of a tetrahedron. The X‐ray crystal structure reveals a tetrahedral symmetry of the molecule and the packing in the crystal is achieved mostly by CH···π interactions since the interstitial solvent molecules prevent the π···π interactions. In solution, tetrahedraphene shows the same electrochemical and photophysical properties as the hexa‐tBu‐substituted HBC (tBu‐HBC) molecule. However, upon water addition, it undergoes a fluorescence change in solution and in the precipitated solid, showing an aggregation induced emission (AIE) process, probably derived from the restriction in the rotation and/or vibration of the HBCs. Time‐Dependent Density Functional Theory (TDDFT) calculations reveal that upon aggregation, the high energy region of the emission band decreases in intensity, whereas the intensity of the red edge emission signal increases and presents a smoother decay, compared to the non‐aggregated molecule. All in all, the excellent correlation between our simulations and the experimental findings allows explaining the colour change observed in the different solutions upon increasing the water fraction.

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Tetrahedraphene: A Csp³‐centered 3D Molecular Nanographene Showing Aggregation‐Induced Emission

Oró,

Romeo‐Gella,

Perles

et al. 2023

Angewandte Chemie

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A Double Twisted Nanographene with a Contorted Pyrene Core

Dong,

Zhang,

Hashikawa

et al. 2024

Angewandte Chemie

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The mature synthetic methodologies enable us to rationally design and produce chiral nanographenes (NGs), most of which consist of multiple helical motifs. However, inherent chirality originating from twisted geometry has just emerged to be employed in chiral NGs. Herein, we report a red‐emissive chiral NG constituted of orthogonally arranged two‐fold twisted π‐skeletons at a contorted pyrene core which contributes to optical transitions of S0 → S1 and vice versa. The thus‐obtained NG exhibited a robustness on its redox properties through 2e– uptake/release. The chemical oxidation generated stable radical cation whose absorption covers near‐infrared I and II regions. Overall, the contorted pyrene core governs electronic nature of the chiral NG. The twist operation on NGs would be, therefore, a design strategy to alter conventional chirality induction on NGs.

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Tetrahedraphene: A Csp³‐centered 3D Molecular Nanographene Showing Aggregation‐Induced Emission

Oró,

Romeo‐Gella,

Perles

et al. 2023

Angew Chem Int Ed

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Construction of hexabenzocoronene-based chiral nanographenes

Cited by 11 publications

References 60 publications

Tetrahedraphene: A Csp³‐centered 3D Molecular Nanographene Showing Aggregation‐Induced Emission

Tetrahedraphene: A Csp³‐centered 3D Molecular Nanographene Showing Aggregation‐Induced Emission

A Double Twisted Nanographene with a Contorted Pyrene Core

Tetrahedraphene: A Csp³‐centered 3D Molecular Nanographene Showing Aggregation‐Induced Emission

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Construction of hexabenzocoronene-based chiral nanographenes

Cited by 11 publications

References 60 publications

Tetrahedraphene: A Csp3‐centered 3D Molecular Nanographene Showing Aggregation‐Induced Emission

Tetrahedraphene: A Csp3‐centered 3D Molecular Nanographene Showing Aggregation‐Induced Emission

A Double Twisted Nanographene with a Contorted Pyrene Core

Tetrahedraphene: A Csp3‐centered 3D Molecular Nanographene Showing Aggregation‐Induced Emission

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Product

Resources

About

Tetrahedraphene: A Csp³‐centered 3D Molecular Nanographene Showing Aggregation‐Induced Emission

Tetrahedraphene: A Csp³‐centered 3D Molecular Nanographene Showing Aggregation‐Induced Emission

Tetrahedraphene: A Csp³‐centered 3D Molecular Nanographene Showing Aggregation‐Induced Emission