Deep-Saddle-Shaped Nanographene Induced by Four Heptagons: Efficient Synthesis and Properties

Borrisov B, Beneventi GM, Fu Y, Qiu ZL, Komber H, Deng QS, Greißel P, Cadranel A, Guldi DM, Ma J, Feng X (2024)

Publication Type: Journal article

Publication year: 2024

Journal

DOI: 10.1021/jacs.4c09224

Abstract

The construction of multiple heptagonal rings in nanographene is the key step for obtaining exotic carbon nanostructures with a negative curvature and intriguing properties. Herein, a novel saddle-shaped nanographene (1) with four embedded heptagons is synthesized via a highly efficient one-shot Scholl reaction from a predesigned oligophenylene precursor. Notably, a quadruple [6]helicene intermediate was also obtained and isolated by controlling the Scholl reaction conditions. Interestingly, the single crystal structures of 1 display a saddle geometry induced by the four embedded heptagons, resulting in a deep curvature with a width of 16.5 Å and a depth of 8.0 Å. Theoretical calculations at the molecular level suggest a weak antiaromatic character of the heptagons in 1. Remarkably, compound 1 exhibits dual fluorescence from S1 and S2. The deep-saddle-shaped geometry in 1 defines host-guest interactions with fullerenes, which were explored in titration experiments and by theoretical methods. The resulting 1@C60 are stable and are subject to an electron transfer from photoexcited 1 to C60. Our current study underscores the influence of heptagon rings on the photophysical, self-assembly, and electron-donating properties of NGs.

Authors with CRIS profile

Involved external institutions

Technische Universität Dresden Germany (DE) Leibniz-Institut für Polymerforschung Dresden e. V. Germany (DE) Xiamen University China (CN) University of Chinese Academy of Sciences China (CN)

How to cite

APA:

Borrisov, B., Beneventi, G.M., Fu, Y., Qiu, Z.L., Komber, H., Deng, Q.S.,... Feng, X. (2024). Deep-Saddle-Shaped Nanographene Induced by Four Heptagons: Efficient Synthesis and Properties. Journal of the American Chemical Society. https://doi.org/10.1021/jacs.4c09224

MLA:

Borrisov, Boris, et al. "Deep-Saddle-Shaped Nanographene Induced by Four Heptagons: Efficient Synthesis and Properties." Journal of the American Chemical Society (2024).

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