Synthesis of a calix[4]arene derivative for isolation of a stable cation radical salt for use as a colorimetric sensor of nitric oxide

Journal of the American Chemical Society

Volumn 126, Issue 42, 2004, Pages 13582-13583

  Rathore, Rajendra ^a   Abdelwahed, Sameh H ^a   Guzei, Ilia A ^a,b  

^a Marquette University   (United States)

^b UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CALIXARENE; CATION; NITRIC OXIDE; RADICAL; SODIUM CHLORIDE;

ABSORPTION SPECTROPHOTOMETRY; ARTICLE; COLORIMETRY; CYCLIC POTENTIOMETRY; ELECTRON; ELECTRON TRANSPORT; OXIDATION; SENSOR; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

BIOSENSING TECHNIQUES; CALIXARENES; CATIONS; COLORIMETRY; FREE RADICALS; KINETICS; NITRIC OXIDE; PHENOLS;

EID: 6444222186     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0454900     Document Type: Article

References (14)

1. (a) Gutsche, C. D. Calixarenes; The Royal Society of Chemistry: Cambridge, UK, 1989.
2. (b) Ikoda, A.; Tsudera, T.; Shinkai, S. J. Org. Chem. 2000, 112, 818.
3. (c) Matthews, S. E.; Schmitt, P.; Felix, V.; Drew, M. G. B.; Beer, P. D. J. Am. Chem. Soc. 2000, 724, 1341.
4. Rathore, R.; Lindeman, S. V.; Rao, K. S. S. P.; Sun, D.; Kochi, J. K. Angew. Chem., Int. Ed. 2000, 39, 2123.
5. (a) Franz, K. J.; Singh, N.; Lippard, S. J. Angew. Chem., Int. Ed. 2000, 39, 2123 and references therein.
6. (b) Rawls, R. Chem. Eng. News 2000, June 19, 11.
7. (c) Itoh, Y.; Ma, F. H.; Hoshi, H.; Oka, M.; Noda, K.; Ukai, Y.; Kojima, H.; Nagano, T.; Toda, N. Anal. Biochem. 2000, 287, 203.
8. For example, see: Steed, J. W.; Juneja, R. K.; Atwood, J. L. Angew. Chem., Int. Ed. Engl. 1994, 33, 2456.
9. Rathore, R. Unpublished results.
10. Rathore, R.; Burns, C. L.; Deselnicu, M. I. Org. Lett. 2001, 3, 2887.
11. Note that the through-space separation between electron-rich dimethoxytolyl groups is >5 Å, and thus electronic coupling amongst them is feasible only through the calixarene core.
12. - (9,10-dimethoxyocta-hydro-1,4:5,8-dimethanoanthracene cation radical), see: Rathore, R.; Burns, C. L. Org. Synth. 2003 (procedure being checked).
13. -1 for NO binding) according to a competition method; see ref 2 for details.
14. For the other methods of nitric oxide sensing, compare: Hilderbrand, S. A.; Lim, H. H.; Lippard, S. J. J. Am. Chem. Soc. 2004, 126, 4972 and references therein.