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Successive construction of cucurbit[8]uril-based covalent organic frameworks from a supramolecular organic framework through photochemical reactions in water

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An Erratum to this article was published on 20 September 2022

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Abstract

Functional framework materials have been developed for many applications including adsorption, asymmetric catalysis, sensing, drug delivery, optical device, and so on. Here, we report the successive construction of two cucurbit[8]uril-based covalent organic frameworks (COFs) including tetraphenylethene-based COF (COF-1) and phenanthrene-based COF (COF-2) from a two-dimensional (2D) periodic cucurbit[8]uril-based supramolecular organic framework (SOF-1) as the prearranged structure via the intermolecular photocycloaddition of the coumarin units and the intramolecular photocyclization of the tetraphenylethene (TPE) units under ultraviolet (UV) irradiation (365 nm) in water. In this case, oxygen (O2) plays an important role in the photocyclization of the TPE units into the phenanthrene units in the transform process from SOF-1 or COF-1 to COF-2. As the TPE units further form phenanthrenes after UV-irradiation, COF-2 exhibits aggregation-caused quenching effect and weak green emission, while COF-1 displays a strong yellow emission due to the aggregation-induced emission. Besides, the adaptive chirality of cationic COF-1 as a biomolecular sensor can be efficiently induced by chiral anionic biomolecules including adenosine-5′-triphosphate (ATP) and adenosine-5′-diphosphate (ADP) to exhibit sensitive negative circular dichroism responses in water. This supramolecular approach to construct COF from SOF via photochemical reactions may open a new opportunity for the construction and application of the water-soluble COFs with well structural controllability, unique photophysical properties, and favorable biocompatibility.

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Acknowledgements

This work was supported by the National Natural Science Foundation of China (22122108, 21971208), the Natural Science Basic Research Plan for Distinguished Young Scholars in Shaanxi Province of China (2021JC-37), and the Fok Ying Tong Education Foundation (171010). L. Cao thanks Huijun Ma for performing HR-TEM experiments.

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  1. These authors contributed equally to this work.

Authors and Affiliations

  1. College of Chemistry and Materials Science, Northwest University, Xi’an, 710069, China

    Yawen Li, Chaochao Yan, Qingfang Li & Liping Cao

  2. Frontier Institute of Science and Technology, Xi’an Jiaotong University, Xi’an, 710054, China

    Yawen Li

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  1. Yawen Li
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  2. Chaochao Yan
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  3. Qingfang Li
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  4. Liping Cao
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Correspondence to Liping Cao.

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The supporting information is available online at http://chem.scichina.com and http://link.springer.com/journal/11426. The supporting materials are published as submitted, without typesetting or editing. The responsibility for scientific accuracy and content remains entirely with the authors.

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The online version of the original article can be found at https://doi.org/10.1007/s11426-022-1393-1

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11426_2022_1231_MOESM1_ESM.pdf

Successive Construction of Cucurbit[8]uril-Based Covalent Or-ganic Frameworks from a Supramolecular Organic Framework Through Photochemical Reactions in Water

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Li, Y., Yan, C., Li, Q. et al. Successive construction of cucurbit[8]uril-based covalent organic frameworks from a supramolecular organic framework through photochemical reactions in water. Sci. China Chem. 65, 1279–1285 (2022). https://doi.org/10.1007/s11426-022-1231-5

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