Authors
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Borrisov, B.; Beneventi, G. M.; Fu, Y.; Qiu, Z.-L.; Komber, H.; Deng, Q.-S.; Greißel, P. M.; Cadranel, A.; Guldi, D. M.; Ma, J.; Feng, X.
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Title
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Deep-saddle-shaped nanographene induced by four heptagons: Efficient synthesis and properties
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Date
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27.09.2024
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Number
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0
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Abstract
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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.
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Publisher
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American Chemical Society
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Wikidata
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Citation
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Journal of the American Chemical Society 146 (2024) 27335-27344
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DOI
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https://doi.org/10.1021/jacs.4c09224
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Tags
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