Selective recognition and electrochemical sensing of dopamine using a ferrocene-based heteroditopic receptor. Issue 43 (24th October 2018)

• Record Type: Journal Article
• Authors: Miyaji, Hidekazu; Komada, Haruka; Goto, Keisuke; Fujimoto, Junko; Kiriyama, Naoaki; Tucker, James H.R.
• Is Part Of: Tetrahedron letters. Volume 59:Issue 43(2018)
• Page Start: 3853
• Page End: 3857
• Publication Date: 2018-10-24
• Subjects: Electrochemical molecular sensor -- Dopamine -- Ferrocene -- Boronic acid -- Crown ether; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2018.09.026
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: A novel ferrocene-based heteroditopic receptor has been synthesized. The receptor recognizes dopamine through multiple point binding interactions. Selective electrochemical sensing of dopamine was demonstrated. Abstract: A redox-active ferrocene-based heteroditopic receptor bearing a boronic acid (as a catechol recognition site) and a benzo-18-crown-6-ether unit (as an ammonium ion recognition site) was synthesized. A 1:1 ditopic complex with dopamine was evidenced by mass spectrometry and NMR spectroscopy. Cyclic voltammetry measurements on the receptor in the presence of a series of organic guest species demonstrated the successful electrochemical sensing of dopamine through a distinct change in the ferrocene-centred redox-couple upon complex formation.