Fluorescent anion sensors based on 4-amino-1,8-naphthalimide that employ the 4-amino N-H

Pfeffer, Frederick, Seter, Marianne, Lewcenko, Naomi and Barnett, Neil 2006, Fluorescent anion sensors based on 4-amino-1,8-naphthalimide that employ the 4-amino N-H, Tetrahedron letters, vol. 47, no. 30, pp. 5241-5245, doi: 10.1016/j.tetlet.2006.05.161.

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Title Fluorescent anion sensors based on 4-amino-1,8-naphthalimide that employ the 4-amino N-H
Author(s) Pfeffer, FrederickORCID iD for Pfeffer, Frederick orcid.org/0000-0002-5441-6437
Seter, Marianne
Lewcenko, Naomi
Barnett, Neil
Journal name Tetrahedron letters
Volume number 47
Issue number 30
Start page 5241
End page 5245
Publisher Elsevier
Place of publication Amsterdam, The Netherlands
Publication date 2006-07-24
ISSN 0040-4039
Summary The new charge neutral 4-amino-1,8-naphthalimide based anion sensors 2 and 3 bind to both acetate and dihydrogenphosphate with 1:1 stoichiometry through hydrogen bonding to both thiourea N–H atoms and in the case of dihydrogenphosphate, the naphthalimide 4 amino N–H group as well. This was clearly established from 1H NMR titration experiments with H2PO4- in DMSO-d6 where a substantial shift in the resonance for the naphthalimide N–H was observed concomitant with the expected migration of the thiourea N–H chemical shifts. The binding constants determined from the titration studies indicate that the new sensors bind H2PO4- more strongly than AcO. Fluorescence titrations with sensor 3 indicate quenching of 59% and 36% upon addition of acetate and dihydrogenphosphate, respectively.
Notes Available online 13 June 2006.
Language eng
DOI 10.1016/j.tetlet.2006.05.161
Field of Research 030302 Nanochemistry and Supramolecular Chemistry
Socio Economic Objective 970103 Expanding Knowledge in the Chemical Sciences
HERDC Research category C1 Refereed article in a scholarly journal
Copyright notice ©2006, Elsevier
Persistent URL http://hdl.handle.net/10536/DRO/DU:30003850

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