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

Release Time:2019-03-13  Hits:

Indexed by: Journal Article

Date of Publication: 2016-05-01

Journal: CHEMICAL PAPERS

Included Journals: Scopus、SCIE

Volume: 70

Issue: 5

Page Number: 663-666

ISSN: 0366-6352

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

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 H-1 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. (c) 2015 Institute of Chemistry, Slovak Academy of Sciences

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