Synthesis of a ditopic homooxacalix[3]arene for fluorescence enhanced detection of heavy and transition metal ions

Redshaw, Carl; Jin, Cheng-Cheng; Mou, Lan; Ni, Xin-Long; Wu, Yanan; Yamato, Takehiko

Abstract

A pyrene-appended ratiometric fluorescent chemosensor L based on a synthetic approach of insulating the fluorophore from the ionophore by a specific molecular spacer has been synthesised and characterised. The fluorescence spectra changes of L suggested that the chemosensor can detect heavy and transition metal (HTM) ions ratiometrically and with variable sensitivity according to the substituents present. ¹H NMR titration experiments indicated that the three triazole ligands prefer binding with Hg²⁺, Pb²⁺ and Zn²⁺, resulting in a conformational change that produces monomer emission of the pyrene accompanied by the excimer quenching. However, the addition of Fe³⁺, which may be accommodated by the cavity of L, makes the pyrene units move closer to each other, and a discernible increase in the emission intensity of the static excimer is observed. Therefore, it is believed that the ditopic scaffold of the calix[3]arene as a specific molecular spacer here plays an important role in the blocking of the heavy atom effect of HTM ions by insulating the fluorophore from the ionophore given the long distance between the metal cation and the pyrene moiety.

Citation

Redshaw, C., Jin, C., Mou, L., Ni, X., Wu, Y., & Yamato, T. (2015). Synthesis of a ditopic homooxacalix[3]arene for fluorescence enhanced detection of heavy and transition metal ions. Supramolecular chemistry, 27(7-8), 501-507. https://doi.org/10.1080/10610278.2014.1002841

• Journal Article Type: Article
• Acceptance Date: Dec 23, 2014
• Online Publication Date: Feb 10, 2015
• Publication Date: Aug 3, 2015
• Deposit Date: Jul 14, 2015
• Publicly Available Date: Jul 14, 2015
• Journal: Supramolecular chemistry
• Print ISSN: 1061-0278
• Electronic ISSN: 1029-0478
• Publisher: Taylor and Francis
• Peer Reviewed: Peer Reviewed
• Volume: 27
• Issue: 7-8
• Pages: 501-507
• DOI: https://doi.org/10.1080/10610278.2014.1002841
• Keywords: Fluorescence, Heavy and transition metal (HTM) ions , Ditopic homooxacalix[3]arene
• Public URL: https://hull-repository.worktribe.com/output/376432
• Publisher URL: http://www.tandfonline.com/doi/full/10.1080/10610278.2014.1002841
• Additional Information: This is an Accepted Manuscript of an article published by Taylor & Francis in Supramolecular chemistry on 10/02/2015, available online: http://wwww.tandfonline.com/10.1080/10610278.2014.1002841