Acceptor engineering of quinone-based cycloparaphenylenes via post-synthesis for achieving white-light emission in single-molecule

Xiaonan Li, Lin Liu, Luyang Jia, Zhe Lian, Jing He, Shengzhu Guo, Ying Wang (), Xuebo Chen () and Hua Jiang ()
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Xiaonan Li: Beijing Normal University
Lin Liu: Beijing Normal University
Luyang Jia: Beijing Normal University
Zhe Lian: Beijing Normal University
Jing He: Beijing Normal University
Shengzhu Guo: Beijing Normal University
Ying Wang: Beijing Normal University
Xuebo Chen: Beijing Normal University
Hua Jiang: Beijing Normal University

Nature Communications, 2025, vol. 16, issue 1, 1-12

Abstract: Abstract Developing donor-acceptor [n]cycloparaphenylenes (D-A [n]CPPs) with multiple emissions from different emissive states remains challenging yet crucial for achieving white-light emission in single-molecule. Here, we report our explorations into acceptor engineering of quinone-based D-A [10]CPPs (Nq/Aq/Tq[10]CPPs) via a post-lateral annulation using Diels-Alder reactions of oxTh[10]CPP. X-ray analysis reveals that Nq[10]CPP displays a side by side packing via naphthoquione stacking while Aq[10]CPP adopts an intercalated conformation through anthraquinone interaction. Fluorescence investigations reveal that the quinone-based [10]CPPs display distinctive acceptor-dependent dual-emission from both the locally excited state and charge transfer state after single-wavelength excitation in organic solvents, consequently leading to multicolor emissions, in particular, white-light emission in CHCl3 for Aq[10]CPP. In THF/water mixture, quinone-based [10]CPPs and oxTh[10]CPP display a wide range of fluorescence emissions including white-light emission as increasing the fraction of water, accompanying by the formation of nanoparticles as demonstrated by Tyndall effect and SEM. Interestingly, the fluorescence of Aq[10]CPP can be switched from white to blue in CHCl3 upon redox. Our investigations demonstrate that acceptor engineering not only endows quinone-based [10]CPPs with two distint emissive states for achieving white-light emission but also highlights an effective post-synthetic strategy for functionalizing CPP nanohoops with desirable properties.

Date: 2025
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DOI: 10.1038/s41467-025-55895-x

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