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A novel intramolecular reversible reaction between the hydroxyl group and isobutenylene chain in a cyclophane-type macrocycle

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Abstract

A novel Hg2+ ion induced reversible ring contraction was achieved employing the intramolecular reaction of isobutylene with an aromatic hydroxyl group of cyclophane; reversibility of the reaction was facilitated by excess addition of NaBH4 which also resulted in complexation. The ring contraction and expansion was monitored by UV-VIS absorption, and by fluorescence and 1H NMR spectra. Switchable fluorescence behavior (on—off—on) was observed when the ring-size was tuned from a 19-membered ring to an 18-membered and vice versa. This fine tuning has the potential to be applied in the construction of new supramolecular devices.

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Authors and Affiliations

  1. State Key Laboratory of Fine Chemicals, School of Chemical Engineering, Dalian University of Technology, Dalian, 116024, China

    Le Fang, Wei-Tao Gong, Manivannan Kalavathi Dhinakaran, Li Shang & Gui-Ling Ning

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  1. Le Fang
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  2. Wei-Tao Gong
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  3. Manivannan Kalavathi Dhinakaran
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  4. Li Shang
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  5. Gui-Ling Ning
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Correspondence to Wei-Tao Gong.

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Fang, L., Gong, WT., Dhinakaran, M.K. et al. A novel intramolecular reversible reaction between the hydroxyl group and isobutenylene chain in a cyclophane-type macrocycle. Chem. Pap. 70, 663–666 (2016). https://doi.org/10.1515/chempap-2015-0241

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  • DOI: https://doi.org/10.1515/chempap-2015-0241

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