Colorimetric ‘naked eye’ sensing of anions using a thiosemicarbazide receptor: a case study of recognition through hydrogen bonding versus deprotonation
Colorimetric ‘naked eye’ sensing of anions using a thiosemicarbazide receptor: a case study of recognition through hydrogen bonding versus deprotonation
The thiosemicarbazide receptors 1 and 2, containing three N–H donors (including a thiourea motif), have been synthesized and studied for their anion binding abilities. The recognition of 1 and 2 with various anions [AcO?, F?, H2PO4?, SO42? and OH? for 1; OAc? and F? for 2] as their tetrabutylammonium salts was studied spectroscopically in CH3CN and EtOH. Significant changes were observed in the UV–vis absorption spectra of 1 which was red-shifted in both solvents when titrated with these anions. A dramatic colour change from yellow to red was also clearly observed. In contrast, the absorption changes for 2 were smaller with a colour change from colourless to yellow. These changes were determined to be due to deprotonation of the central N–H moiety (belonging to the thiourea) and not due to hydrogen bonding of these anions to the receptors. This was confirmed using single crystal X-ray crystallography, as crystals of 1 grown with TBAAc were found to correspond to the deprotonated structure 3.
anion sensing, recognition, hydrogen bonding, deprotonation, colorimetric, thiourea, supramolecular chemistry
2770-2775
Pandurangan, Komala
c4eb9960-26ee-4ddf-886f-e4b193a18e4f
Kitchen, Jonathan A.
3999f5cb-d53e-4c51-b750-627bd2a1b9b6
Gunnlaugsson, Thorfinnur
bbfcaaa6-2aca-47c9-9b7b-954442218f50
May 2013
Pandurangan, Komala
c4eb9960-26ee-4ddf-886f-e4b193a18e4f
Kitchen, Jonathan A.
3999f5cb-d53e-4c51-b750-627bd2a1b9b6
Gunnlaugsson, Thorfinnur
bbfcaaa6-2aca-47c9-9b7b-954442218f50
Pandurangan, Komala, Kitchen, Jonathan A. and Gunnlaugsson, Thorfinnur
(2013)
Colorimetric ‘naked eye’ sensing of anions using a thiosemicarbazide receptor: a case study of recognition through hydrogen bonding versus deprotonation.
Tetrahedron Letters, 54 (22), .
(doi:10.1016/j.tetlet.2013.02.107).
Abstract
The thiosemicarbazide receptors 1 and 2, containing three N–H donors (including a thiourea motif), have been synthesized and studied for their anion binding abilities. The recognition of 1 and 2 with various anions [AcO?, F?, H2PO4?, SO42? and OH? for 1; OAc? and F? for 2] as their tetrabutylammonium salts was studied spectroscopically in CH3CN and EtOH. Significant changes were observed in the UV–vis absorption spectra of 1 which was red-shifted in both solvents when titrated with these anions. A dramatic colour change from yellow to red was also clearly observed. In contrast, the absorption changes for 2 were smaller with a colour change from colourless to yellow. These changes were determined to be due to deprotonation of the central N–H moiety (belonging to the thiourea) and not due to hydrogen bonding of these anions to the receptors. This was confirmed using single crystal X-ray crystallography, as crystals of 1 grown with TBAAc were found to correspond to the deprotonated structure 3.
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Published date: May 2013
Keywords:
anion sensing, recognition, hydrogen bonding, deprotonation, colorimetric, thiourea, supramolecular chemistry
Organisations:
Organic Chemistry: Synthesis, Catalysis and Flow
Identifiers
Local EPrints ID: 352612
URI: http://eprints.soton.ac.uk/id/eprint/352612
ISSN: 0040-4039
PURE UUID: 6546bec0-79ca-4c70-b66b-3a24fdff4346
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Date deposited: 20 May 2013 09:25
Last modified: 14 Mar 2024 13:54
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Contributors
Author:
Komala Pandurangan
Author:
Jonathan A. Kitchen
Author:
Thorfinnur Gunnlaugsson
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