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A long wavelength colourimetric chemosensor for fluoride

A long wavelength colourimetric chemosensor for fluoride
A long wavelength colourimetric chemosensor for fluoride

A family of chemosensors based on the squaramidoquinoxaline moiety (cyclobuta[b]quinoxaline-1,2(3H,8H)-dione) (1–3) have been assembled by a simple room temperature one step synthesis. X-ray crystallographic analysis of 2 demonstrated both strong hydrogen bond donor ability and tendency to π stack in the solid state. Moreover, Compound 2, with its strongly electron withdrawing nitro-substituent, showed an obvious F selective colour change (when measured against other halides) clearly visible to the naked eye from pink to green in DMSO solution. Further addition of F led to a second colour change from green to yellow. Using TD-DFT, UV/Vis and NMR analysis we conclude that the observed colour changes are likely to be due to a two-step process involving two NH deprotonation steps. Colour changes of 1 and 3 were not as apparent in the presence of F owing to the reduced acidity of the NH functionality of the squaramidoquinoxaline. The results of this study again demonstrate the use of squaramide derivatives as valuable building blocks in the field of anion recognition and demonstrate that the electron withdrawing aryl substituent is directly related to the sensing ability/acidity of the squaramide protons and can be used to tune their anion recognition behavior.

Anion sensing, colorimetric, fluoride, squaramide
1061-0278
1-11
Marchetti, Luke A.
8b8968f0-447c-48ae-a288-811a24d50863
Mao, Nan
04820276-e2f5-4a7f-b398-2f34bdb9254c
Krämer, Tobias
ec6f3fa8-ebd2-4bb6-986f-7943997bd719
Kitchen, Jonathan A.
3999f5cb-d53e-4c51-b750-627bd2a1b9b6
Elmes, Robert B.P.
67d1c256-18a7-432c-8452-03369b6ddb95
Marchetti, Luke A.
8b8968f0-447c-48ae-a288-811a24d50863
Mao, Nan
04820276-e2f5-4a7f-b398-2f34bdb9254c
Krämer, Tobias
ec6f3fa8-ebd2-4bb6-986f-7943997bd719
Kitchen, Jonathan A.
3999f5cb-d53e-4c51-b750-627bd2a1b9b6
Elmes, Robert B.P.
67d1c256-18a7-432c-8452-03369b6ddb95

Marchetti, Luke A., Mao, Nan, Krämer, Tobias, Kitchen, Jonathan A. and Elmes, Robert B.P. (2018) A long wavelength colourimetric chemosensor for fluoride. Supramolecular Chemistry, 1-11. (doi:10.1080/10610278.2018.1461873).

Record type: Article

Abstract

A family of chemosensors based on the squaramidoquinoxaline moiety (cyclobuta[b]quinoxaline-1,2(3H,8H)-dione) (1–3) have been assembled by a simple room temperature one step synthesis. X-ray crystallographic analysis of 2 demonstrated both strong hydrogen bond donor ability and tendency to π stack in the solid state. Moreover, Compound 2, with its strongly electron withdrawing nitro-substituent, showed an obvious F selective colour change (when measured against other halides) clearly visible to the naked eye from pink to green in DMSO solution. Further addition of F led to a second colour change from green to yellow. Using TD-DFT, UV/Vis and NMR analysis we conclude that the observed colour changes are likely to be due to a two-step process involving two NH deprotonation steps. Colour changes of 1 and 3 were not as apparent in the presence of F owing to the reduced acidity of the NH functionality of the squaramidoquinoxaline. The results of this study again demonstrate the use of squaramide derivatives as valuable building blocks in the field of anion recognition and demonstrate that the electron withdrawing aryl substituent is directly related to the sensing ability/acidity of the squaramide protons and can be used to tune their anion recognition behavior.

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More information

Accepted/In Press date: 15 March 2018
e-pub ahead of print date: 18 April 2018
Keywords: Anion sensing, colorimetric, fluoride, squaramide

Identifiers

Local EPrints ID: 422494
URI: http://eprints.soton.ac.uk/id/eprint/422494
ISSN: 1061-0278
PURE UUID: bd023362-5c6f-4607-a956-b6a8e285c25d
ORCID for Jonathan A. Kitchen: ORCID iD orcid.org/0000-0002-7139-5666

Catalogue record

Date deposited: 24 Jul 2018 16:31
Last modified: 09 Nov 2021 13:25

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Contributors

Author: Luke A. Marchetti
Author: Nan Mao
Author: Tobias Krämer
Author: Jonathan A. Kitchen ORCID iD
Author: Robert B.P. Elmes

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