Fluorescent probe for sequential recognition of Ga3+ and pyrophosphate anions

Chiseop Lim; Miran An; Hansol Seo; Joon Hyuk Huh; Anup Pandith; Aasif Helal; Hong Seok Kim

doi:10.1016/j.snb.2016.11.002

Fluorescent probe for sequential recognition of Ga³⁺ and pyrophosphate anions

Chiseop Lim, Miran An, Hansol Seo, Joon Hyuk Huh, Anup Pandith, Aasif Helal, Hong Seok Kim

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

48 Citations (Scopus)

Abstract

Three novel fluorescent probes, 2-(2′-hydroxyphenyl)-4-chloromethylthiazole (1), 2-(2′-hydroxyphenyl)-4-hydroxymethylthiazole (3), and 2-(2′-hydroxyphenyl)-4-iodomethylthiazole (4) were designed for the sequential recognition of Ga³⁺ and pyrophosphate ions in acetonitrile. Probe 1 selectively detected Ga³⁺ through a “switch on” response, showing a good association constant (K_a = 6.24 × 10⁴ M⁻¹) and binding with Ga³⁺ ions in a 1:1 stoichiometry. An in situ generated 1-Ga³⁺ (1:1) ensemble detected H₂P₂O₇^3–ions sequentially through a “switch off” response. The “switch on” response occurred with selective complexation of Ga³⁺ ions due to combined excited state intramolecular proton transfer (ESIPT) and chelation induced enhanced fluorescence (CHEF) effects. An ensemble of 1 and gallium(III) was more selective for pyrophosphate ions than any other anion.

Original language	English
Pages (from-to)	789-799
Number of pages	11
Journal	Sensors and Actuators, B: Chemical
Volume	241
DOIs	https://doi.org/10.1016/j.snb.2016.11.002
Publication status	Published - Mar 31 2017
Externally published	Yes

Keywords

Fluorescence probe
Gallium ion-selective
Pyrophosphate
Sequential recognition
Thiazole

ASJC Scopus subject areas

Electronic, Optical and Magnetic Materials
Instrumentation
Condensed Matter Physics
Surfaces, Coatings and Films
Metals and Alloys
Electrical and Electronic Engineering
Materials Chemistry

Access to Document

10.1016/j.snb.2016.11.002

Cite this

@article{269047ed83c7401c91c725c23d4c482b,

title = "Fluorescent probe for sequential recognition of Ga3+ and pyrophosphate anions",

abstract = "Three novel fluorescent probes, 2-(2′-hydroxyphenyl)-4-chloromethylthiazole (1), 2-(2′-hydroxyphenyl)-4-hydroxymethylthiazole (3), and 2-(2′-hydroxyphenyl)-4-iodomethylthiazole (4) were designed for the sequential recognition of Ga3+ and pyrophosphate ions in acetonitrile. Probe 1 selectively detected Ga3+ through a “switch on” response, showing a good association constant (Ka = 6.24 × 104 M−1) and binding with Ga3+ ions in a 1:1 stoichiometry. An in situ generated 1-Ga3+ (1:1) ensemble detected H2P2O73–ions sequentially through a “switch off” response. The “switch on” response occurred with selective complexation of Ga3+ ions due to combined excited state intramolecular proton transfer (ESIPT) and chelation induced enhanced fluorescence (CHEF) effects. An ensemble of 1 and gallium(III) was more selective for pyrophosphate ions than any other anion.",

keywords = "Fluorescence probe, Gallium ion-selective, Pyrophosphate, Sequential recognition, Thiazole",

author = "Chiseop Lim and Miran An and Hansol Seo and Huh, {Joon Hyuk} and Anup Pandith and Aasif Helal and Kim, {Hong Seok}",

note = "Funding Information: This research was supported by the Basic Science Research Program of the National Research Foundation of Korea (NRF) funded by Republic of Korea ( 2013R1A1A2006777 ). Publisher Copyright: {\textcopyright} 2016 Elsevier B.V.",

year = "2017",

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doi = "10.1016/j.snb.2016.11.002",

language = "English",

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T1 - Fluorescent probe for sequential recognition of Ga3+ and pyrophosphate anions

AU - Lim, Chiseop

AU - An, Miran

AU - Seo, Hansol

AU - Huh, Joon Hyuk

AU - Pandith, Anup

AU - Helal, Aasif

AU - Kim, Hong Seok

N1 - Funding Information: This research was supported by the Basic Science Research Program of the National Research Foundation of Korea (NRF) funded by Republic of Korea ( 2013R1A1A2006777 ). Publisher Copyright: © 2016 Elsevier B.V.

PY - 2017/3/31

Y1 - 2017/3/31

N2 - Three novel fluorescent probes, 2-(2′-hydroxyphenyl)-4-chloromethylthiazole (1), 2-(2′-hydroxyphenyl)-4-hydroxymethylthiazole (3), and 2-(2′-hydroxyphenyl)-4-iodomethylthiazole (4) were designed for the sequential recognition of Ga3+ and pyrophosphate ions in acetonitrile. Probe 1 selectively detected Ga3+ through a “switch on” response, showing a good association constant (Ka = 6.24 × 104 M−1) and binding with Ga3+ ions in a 1:1 stoichiometry. An in situ generated 1-Ga3+ (1:1) ensemble detected H2P2O73–ions sequentially through a “switch off” response. The “switch on” response occurred with selective complexation of Ga3+ ions due to combined excited state intramolecular proton transfer (ESIPT) and chelation induced enhanced fluorescence (CHEF) effects. An ensemble of 1 and gallium(III) was more selective for pyrophosphate ions than any other anion.

AB - Three novel fluorescent probes, 2-(2′-hydroxyphenyl)-4-chloromethylthiazole (1), 2-(2′-hydroxyphenyl)-4-hydroxymethylthiazole (3), and 2-(2′-hydroxyphenyl)-4-iodomethylthiazole (4) were designed for the sequential recognition of Ga3+ and pyrophosphate ions in acetonitrile. Probe 1 selectively detected Ga3+ through a “switch on” response, showing a good association constant (Ka = 6.24 × 104 M−1) and binding with Ga3+ ions in a 1:1 stoichiometry. An in situ generated 1-Ga3+ (1:1) ensemble detected H2P2O73–ions sequentially through a “switch off” response. The “switch on” response occurred with selective complexation of Ga3+ ions due to combined excited state intramolecular proton transfer (ESIPT) and chelation induced enhanced fluorescence (CHEF) effects. An ensemble of 1 and gallium(III) was more selective for pyrophosphate ions than any other anion.

KW - Fluorescence probe

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KW - Sequential recognition

KW - Thiazole

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