Synthesis, Photophysical and Supramolecular Properties of a π-Conjugated Molecular Crown Containing a Pentagonal Unit: A Model Compound for Fullerene C240

Qiang Huang; Yayu Wu; Yu Zhou; Huiqing Liu; Jinyi Wang; Shengda Wang; Pingwu Du

doi:10.1055/s-0040-1707963

Synthesis, Table of Contents

Synthesis 2020; 52(17): 2535-2540
DOI: 10.1055/s-0040-1707963

paper

Synthesis, Photophysical and Supramolecular Properties of a π-Conjugated Molecular Crown Containing a Pentagonal Unit: A Model Compound for Fullerene C₂₄₀

Qiang Huang

,

Yayu Wu

,

Yu Zhou

,

Huiqing Liu

,

Jinyi Wang

,

Shengda Wang

,

Pingwu Du∗

Hefei National Laboratory for Physical Sciences at the Microscale, iChEM (Collaborative Innovation Center of Chemistry for Energy Materials), CAS Key Laboratory of Materials for Energy Conversion, Department of Materials Science and Engineering, University of Science and Technology of China (USTC), 96 Jinzhai Road, Hefei, Anhui Province, 230026, P. R. of China Email: dupingwu@ustc.edu.cn

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Abstract

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Abstract

The total synthesis of carbon onions is a significant challenge in the fields of materials science and organic chemistry. To date, the synthesis of even a fragment of fullerene C₂₄₀ and its smallest carbon onion C₆₀@C₂₄₀ remains poorly explored. Herein, we demonstrate a bottom-up strategy to produce a novel π-extended molecular crown-shaped molecule (MC3) containing curved pentagonal and hexagonal units. This molecular crown represents a curved model compound for fullerene C₂₄₀ and is fully characterized by NMR, mass spectrometry, UV-vis absorption, and from its emission spectra. Its supramolecular host–guest interaction with fullerene C₆₀ is also investigated. MC3 and C₆₀@MC3 can potentially be employed as seeds or templates for the bottom-up synthesis of fullerene C₂₄₀ and the carbon onion C₆₀@C₂₄₀, respectively.

Key words

carbon onion - fullerenes - macrocycles - bottom-up synthesis - supramolecular chemistry

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References

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