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Reversible manipulation of organic dye aggregation through acyclic cucurbit[n]uril-based host-guest complexation

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Abstract

We use a highly water-soluble acyclic cucurbit[n]uril ACB-01 that bears eight carboxylate groups. ACB-01 has excellent solubility in water and high affinity to the cyanine dyes pseudoisocyanine (PIC) and pinacyanol (PIN) to afford 1:1 complexes. The complexation has been studied by UV–vis absorption, fluorescence and nuclear magnetic resonance (NMR) spectroscopy, and the binding constants (Ka) are determined to be (1.54 ± 0.15) × 106 M−1 and (6.09 ± 0.82) × 105 M−1, respectively. This complexation leads to the inhibition of the J-aggregation of PIC and H-aggregation of PIN. However, competitive guests methyl viologen and 1-adamantanamine hydrochloride can recover their respective J- and H-aggregation due to more stable complexation occurs between them and ACB-01. Thus, we have established a new method of reversibly controlling dye aggregation by regulating the concentration of ACB-01 and competitive guests.

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Acknowledgements

We are grateful to the National Natural Science Foundation of China (NSFC) for financial support (21921003, 21890730 and 21890732).

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Authors and Affiliations

  1. Department of Chemistry, Shanghai Key Laboratory of Molecular Catalysis and Innovative Materials, Fudan University, Shanghai, 200438, China

    Wen-Chang Peng, Hui Wang, Dan-Wei Zhang & Zhan-Ting Li

  2. School of Pharmaceutical Engineering & Institute for Advanced Studies, Taizhou University, 1139 Shifu Avenue, Taizhou, 318000, Zhejiang, China

    Da Ma

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ZL and DM conceived the project, WP conducted the experiments and analyzed the data, WP, HW, DZ, ZL and DM wrote the paper.

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Correspondence to Zhan-Ting Li or Da Ma.

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Peng, WC., Wang, H., Zhang, DW. et al. Reversible manipulation of organic dye aggregation through acyclic cucurbit[n]uril-based host-guest complexation. J Incl Phenom Macrocycl Chem 104, 7–13 (2024). https://doi.org/10.1007/s10847-023-01209-x

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