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Sensing of Antipyretic Carboxylates by Simple Chromogenic Calix[4]pyrroles
Abstract
We present a simple, two- or three-step method for the synthesis of chromogenic octamethylcalix[4]pyrrole-based (OMCP) sensors for anions. Electrophilic aromatic substitution allows for converting the pyrrole moieties of OMCP into a dye. The formation of a sensor-anion complex results in partial charge transfer and a dramatic change in color. The absorption (UV-vis) and NMR titration experiments show that the chromogenic OMCPs sense anions administered as aqueous solutions, even at high ionic strength ( approximately 0.1 M NaCl), while displaying selectivity for pyrophosphate and carboxylate anions. The experiments with polyurethane sensor films show a strong response for aqueous carboxylates, such as antipyretics naproxen approximately ibuprofen > salicylate, without being biased by bicarbonate or carboxy termini of blood plasma proteins.
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Citations
Cited by
Gunnlaugsson, T., Glynn, M., Tocci (née Hussey), G. M., Kruger, P. E., & Pfeffer, F. M. (2006) · Coordination Chemistry Reviews · doi:10.1016/j.ccr.2006.08.017 · Cited by 1,257
Anion receptors based on organic frameworks: highlights from 2005 and 2006
Gale, P. A., García-Garrido, S. E., & Garric, J. (2008) · Chem. Soc. Rev. · doi:10.1039/b715825d · Cited by 782
Recognition and sensing of fluoride anion
Cametti, M., & Rissanen, K. (2009) · Chemical Communications · doi:10.1039/b902069a · Cited by 654
Artificial Receptors for the Recognition of Phosphorylated Molecules
Hargrove, A. E., Nieto, S., Zhang, T., Sessler, J. L., & Anslyn, E. V. (2011) · Chemical Reviews · doi:10.1021/cr100242s · Cited by 649
Supramolecular fluorescent sensors: An historical overview and update
Guo, C., Sedgwick, A. C., Hirao, T., & Sessler, J. L. (2021) · Coordination Chemistry Reviews · doi:10.1016/j.ccr.2020.213560 · Cited by 284
Metadata
- Authors
- Nishiyabu, R., & Anzenbacher, P.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2005-05-24
- Volume
- 127
- Issue
- 23
- Pages
- 8270-8271
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2081989304
- Cited by
- 216
- References
- 0
- FWCI
- 6.51
- Type
- journal article
- Language
- en
- Open access
- closed
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- Nishiyabu, R., & Anzenbacher, P. (2005). Sensing of Antipyretic Carboxylates by Simple Chromogenic Calix[4]pyrroles. Journal of the American Chemical Society. https://doi.org/10.1021/ja051421p
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