Highly selective fluorescent probe for sequential recognition of copper(II) and iodide ions

Hansol Seo; Miran An; Bo Yeon Kim; Jun Hyeak Choi; Aasif Helal; Hong Seok Kim

doi:10.1016/j.tet.2017.06.034

Highly selective fluorescent probe for sequential recognition of copper(II) and iodide ions

Hansol Seo, Miran An, Bo Yeon Kim, Jun Hyeak Choi, Aasif Helal, Hong Seok Kim^*

^*Corresponding author for this work

Interdisciplinary Research Center for Hydrogen Technologies and Carbon Management

Research output: Contribution to journal › Article › peer-review

55 Scopus citations

Abstract

A new highly selective fluorescent probe based on 2-(2′-aminolphenyl)-4-hydroxymethylthiazole (1) was developed for the detection of copper and iodide ions in ethanol. Probe 1 selectively detected Cu²⁺ through a “switch off” response, showing a good association constant (K_a = 1.43 × 10⁵ M⁻¹) and binding with Cu²⁺ ions in a 1:1 stoichiometry. An in situ generated 1-Cu²⁺ (1:1) ensemble detected I⁻ ions sequentially through a “switch on” response. The “switch off” response occurred with selective complexation of Cu²⁺ ions due to intramolecular charge transfer (ICT). An ensemble of 1 and copper(II) showed higher selectivity towards iodide than towards any other anions due to the reduction of Cu²⁺ to Cu⁺ by I⁻ and subsequent complexation with 1.

Original language	English
Pages (from-to)	4684-4691
Number of pages	8
Journal	Tetrahedron
Volume	73
Issue number	31
DOIs	https://doi.org/10.1016/j.tet.2017.06.034
State	Published - 2017

Bibliographical note

Publisher Copyright:
© 2017 Elsevier Ltd

Keywords

Aminophenylthiazole
Copper ion-selective
Fluorescence probe
Iodide
Sequential recognition

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2017.06.034

Cite this

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title = "Highly selective fluorescent probe for sequential recognition of copper(II) and iodide ions",

abstract = "A new highly selective fluorescent probe based on 2-(2′-aminolphenyl)-4-hydroxymethylthiazole (1) was developed for the detection of copper and iodide ions in ethanol. Probe 1 selectively detected Cu2+ through a “switch off” response, showing a good association constant (Ka = 1.43 × 105 M−1) and binding with Cu2+ ions in a 1:1 stoichiometry. An in situ generated 1-Cu2+ (1:1) ensemble detected I− ions sequentially through a “switch on” response. The “switch off” response occurred with selective complexation of Cu2+ ions due to intramolecular charge transfer (ICT). An ensemble of 1 and copper(II) showed higher selectivity towards iodide than towards any other anions due to the reduction of Cu2+ to Cu+ by I− and subsequent complexation with 1.",

keywords = "Aminophenylthiazole, Copper ion-selective, Fluorescence probe, Iodide, Sequential recognition",

author = "Hansol Seo and Miran An and Kim, \{Bo Yeon\} and Choi, \{Jun Hyeak\} and Aasif Helal and Kim, \{Hong Seok\}",

note = "Publisher Copyright: {\textcopyright} 2017 Elsevier Ltd",

year = "2017",

doi = "10.1016/j.tet.2017.06.034",

language = "English",

volume = "73",

pages = "4684--4691",

journal = "Tetrahedron",

issn = "0040-4020",

number = "31",

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TY - JOUR

T1 - Highly selective fluorescent probe for sequential recognition of copper(II) and iodide ions

AU - Seo, Hansol

AU - An, Miran

AU - Kim, Bo Yeon

AU - Choi, Jun Hyeak

AU - Helal, Aasif

AU - Kim, Hong Seok

PY - 2017

Y1 - 2017

N2 - A new highly selective fluorescent probe based on 2-(2′-aminolphenyl)-4-hydroxymethylthiazole (1) was developed for the detection of copper and iodide ions in ethanol. Probe 1 selectively detected Cu2+ through a “switch off” response, showing a good association constant (Ka = 1.43 × 105 M−1) and binding with Cu2+ ions in a 1:1 stoichiometry. An in situ generated 1-Cu2+ (1:1) ensemble detected I− ions sequentially through a “switch on” response. The “switch off” response occurred with selective complexation of Cu2+ ions due to intramolecular charge transfer (ICT). An ensemble of 1 and copper(II) showed higher selectivity towards iodide than towards any other anions due to the reduction of Cu2+ to Cu+ by I− and subsequent complexation with 1.

AB - A new highly selective fluorescent probe based on 2-(2′-aminolphenyl)-4-hydroxymethylthiazole (1) was developed for the detection of copper and iodide ions in ethanol. Probe 1 selectively detected Cu2+ through a “switch off” response, showing a good association constant (Ka = 1.43 × 105 M−1) and binding with Cu2+ ions in a 1:1 stoichiometry. An in situ generated 1-Cu2+ (1:1) ensemble detected I− ions sequentially through a “switch on” response. The “switch off” response occurred with selective complexation of Cu2+ ions due to intramolecular charge transfer (ICT). An ensemble of 1 and copper(II) showed higher selectivity towards iodide than towards any other anions due to the reduction of Cu2+ to Cu+ by I− and subsequent complexation with 1.

KW - Aminophenylthiazole

KW - Copper ion-selective

KW - Fluorescence probe

KW - Iodide

KW - Sequential recognition

UR - https://www.scopus.com/pages/publications/85021746119

U2 - 10.1016/j.tet.2017.06.034

DO - 10.1016/j.tet.2017.06.034

M3 - Article

AN - SCOPUS:85021746119

SN - 0040-4020

VL - 73

SP - 4684

EP - 4691

JO - Tetrahedron

JF - Tetrahedron

IS - 31

ER -

Highly selective fluorescent probe for sequential recognition of copper(II) and iodide ions

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

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