Selective recognition and electrochemical sensing of dopamine using a ferrocene-based heteroditopic receptor

Hidekazu Miyaji; Haruka Komada; Keisuke Goto; Junko Fujimoto; Naoaki Kiriyama; James H. R. Tucker

doi:10.1016/j.tetlet.2018.09.026

Selective recognition and electrochemical sensing of dopamine using a ferrocene-based heteroditopic receptor

Hidekazu Miyaji, Haruka Komada, Keisuke Goto, Junko Fujimoto, Naoaki Kiriyama, James H. R. Tucker

Chemistry

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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.

Original language	English
Pages (from-to)	3853-3857
Journal	Tetrahedron Letters
Early online date	11 Sept 2018
DOIs	https://doi.org/10.1016/j.tetlet.2018.09.026
Publication status	Published - 24 Oct 2018

Keywords

Electrochemical molecular sensor
Dopamine
Ferrocene
Boronic acid
Crown ether

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10.1016/j.tetlet.2018.09.026Licence: None: All rights reserved

Miyaji_et_al_Selective recognition and electrochemical sensing_Tetrahedron_LettersAccepted author manuscript, 251 KBLicence: Creative Commons: Attribution-NonCommercial-NoDerivs (CC BY-NC-ND)

https://linkinghub.elsevier.com/retrieve/pii/S0040403918311079Licence: None: All rights reserved

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title = "Selective recognition and electrochemical sensing of dopamine using a ferrocene-based heteroditopic receptor",

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.",

keywords = "Electrochemical molecular sensor, Dopamine, Ferrocene, Boronic acid, Crown ether",

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T1 - Selective recognition and electrochemical sensing of dopamine using a ferrocene-based heteroditopic receptor

AU - Miyaji, Hidekazu

AU - Komada, Haruka

AU - Goto, Keisuke

AU - Fujimoto, Junko

AU - Kiriyama, Naoaki

AU - Tucker, James H. R.

PY - 2018/10/24

Y1 - 2018/10/24

N2 - 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.

AB - 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.

KW - Electrochemical molecular sensor

KW - Dopamine

KW - Ferrocene

KW - Boronic acid

KW - Crown ether

U2 - 10.1016/j.tetlet.2018.09.026

DO - 10.1016/j.tetlet.2018.09.026

M3 - Article

SN - 0040-4039

SP - 3853

EP - 3857

JO - Tetrahedron Letters

JF - Tetrahedron Letters

ER -

Selective recognition and electrochemical sensing of dopamine using a ferrocene-based heteroditopic receptor

Abstract

Keywords

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