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

  • Le Fang , Wei-Tao Gong EMAIL logo , Manivannan Kalavathi Dhinakaran , Li Shang and Gui-Ling Ning
Published/Copyright: February 11, 2016
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Chemical Papers
From the journal Chemical Papers Volume 70 Issue 5

Anovel 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 1HNMR 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.

Keywords: cyclophane; reversible reaction; ring-size of macrocycle; supramolecular devices

Acknowledgements.

This research has been supported by the National Natural Science Foundation of China (No. 21206016) and the Fundamental Research Funds for the Central Universities (DUT11LK13).

Supplementary data

Supplementary data associated with this article (A novel intramolecular reversible reaction between the hydroxyl group and isobutenylene chain in a cyclophane-type macrocycle) can be found in the online version of this paper (DOI: 10.1515/chempap-2015-0241).

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Received: 2015-6-15
Revised: 2015-9-27
Accepted: 2015-10-21
Published Online: 2016-2-11
Published in Print: 2016-5-1

© 2015 Institute of Chemistry, Slovak Academy of Sciences

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https://doi.org/10.1515/chempap-2015-0241
Keywords for this article
cyclophane; reversible reaction; ring-size of macrocycle; supramolecular devices

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  1. Original Paper
  2. Preparation and characterisation of gelatine hydrogels predisposed to use as matrices for effective immobilisation of biocatalystst‡
  3. Original Paper
  4. Photocatalytic reduction of nitro aromatic compounds to amines using a nanosized highly active CdS photocatalyst under sunlight and blue LED irradiation
  5. Original Paper
  6. Synthesis of butyrate using a heterogeneous catalyst based on polyvinylpolypyrrolidone
  7. Original Paper
  8. Behaviour of selected pesticide residues in blackcurrants (Ribes nigrum) during technological processing monitored by liquid-chromatography tandem mass spectrometry
  9. Original Paper
  10. Influence of solvents and novel extraction methods on bioactive compounds and antioxidant capacity of Phyllanthus amarus
  11. Original Paper
  12. Investigation of phytochemicals and antioxidant capacity of selected Eucalyptus species using conventional extraction
  13. Original Paper
  14. Innovative approach to treating waste waters by a membrane capacitive deionisation system
  15. Original Paper
  16. Liquid—liquid equilibria of ternary systems of 1-hexene/hexane and extraction solvents
  17. Original Paper
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  19. Original Paper
  20. Kinetic study of non-reactive iron removal from iron-gall inks
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  31. Short Communication
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  33. Erratum
  34. Erratum to “Adriana Bakalova, Boryana Nikolova-Mladenova, Rossen Buyukliev, Emiliya Cherneva, Georgi Momekov, Darvin Ivanov: Synthesis, DFT calculations and characterisation of new mixed Pt(II) complexes with 3-thiolanespiro-5′-hydantoin and 4-thio-1H-tetrahydropyranspiro-5′-hydantoin”, Chemical Papers 70 (1) 93–100 (2016)*
  35. Erratum
  36. Erratum to “Martyna Rzelewska, Monika Baczyńska, Magdalena Regel-Rosocka, Maciej Wiśniewski: Trihexyl(tetradecyl)phosphonium bromide as extractant for Rh(III), Ru(III) and Pt(IV) from chloride solutions”, Chemical Papers 70 (4) 454–460 (2016)*
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