Fluorescent Organometallic Sensors for the Detection of Chemical-Warfare-Agent Mimics†
Daniel Knapton Dr.
Department of Macromolecular Science and Engineering, Case Western Reserve University, 2100 Adelbert Road, Cleveland OH 44106-7202, USA, Fax: (+1) 216-368-4202
Search for more papers by this authorMark Burnworth
Department of Macromolecular Science and Engineering, Case Western Reserve University, 2100 Adelbert Road, Cleveland OH 44106-7202, USA, Fax: (+1) 216-368-4202
Search for more papers by this authorStuart J. Rowan Prof. Dr.
Department of Macromolecular Science and Engineering, Case Western Reserve University, 2100 Adelbert Road, Cleveland OH 44106-7202, USA, Fax: (+1) 216-368-4202
Search for more papers by this authorChristoph Weder Prof. Dr.
Department of Macromolecular Science and Engineering, Case Western Reserve University, 2100 Adelbert Road, Cleveland OH 44106-7202, USA, Fax: (+1) 216-368-4202
Search for more papers by this authorDaniel Knapton Dr.
Department of Macromolecular Science and Engineering, Case Western Reserve University, 2100 Adelbert Road, Cleveland OH 44106-7202, USA, Fax: (+1) 216-368-4202
Search for more papers by this authorMark Burnworth
Department of Macromolecular Science and Engineering, Case Western Reserve University, 2100 Adelbert Road, Cleveland OH 44106-7202, USA, Fax: (+1) 216-368-4202
Search for more papers by this authorStuart J. Rowan Prof. Dr.
Department of Macromolecular Science and Engineering, Case Western Reserve University, 2100 Adelbert Road, Cleveland OH 44106-7202, USA, Fax: (+1) 216-368-4202
Search for more papers by this authorChristoph Weder Prof. Dr.
Department of Macromolecular Science and Engineering, Case Western Reserve University, 2100 Adelbert Road, Cleveland OH 44106-7202, USA, Fax: (+1) 216-368-4202
Search for more papers by this authorThe material reported herein is based on work supported by the US army research office (Grant No. DAAD19-03-1-0208), the National Science Foundation (Grant No. CAREER-CHE 0133164), and the Case School of Engineering. The authors also thank Eric Giles, Casey Johnson, and Dr. Parameswar K. Iyer for their assistance.
Graphical Abstract
Mixing and matching: The highly selective detection of chemical-warfare-agent mimics can be achieved by judicious combination of carefully designed fluorescent ligands and metal ions. Designed sensor arrays of these multimetal/multiligand systems represent a modular and versatile approach for the detection of organophosphates and other analytes.
Supporting Information
Supporting information for this article is available on the WWW under http://www.wiley-vch.de/contents/jc_2002/2006/z601634_s.pdf or from the author.
Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.
References
- 1
- 1aS. M. Somani, Chemical Warfare Agent, Academic Press, San Diego, 1992;
- 1bC. H. Gunderson, C. R. Lehmann, F. R. Sidell, B. Jabbari, Neurology 1992, 42, 946;
- 1cS. U. Khan, Pesticides in the Soil Environment, Elsevier, Amsterdam, 1980.
- 2
- 2aJ. A. Ashley, C.-H. Lin, K. D. Wirsching, K. D. Janda, Angew. Chem. 1999, 111, 1909;
10.1002/(SICI)1521-3757(19990614)111:12<1909::AID-ANGE1909>3.0.CO;2-J Google ScholarAngew. Chem. Int. Ed. 1999, 38, 1793;10.1002/(SICI)1521-3773(19990614)38:12<1793::AID-ANIE1793>3.0.CO;2-U CAS PubMed Web of Science® Google Scholar
- 2bS. D. Richardson, Chem. Rev. 2001, 101, 211;
- 2cD. Prosnitz, Science 2005, 310, 978;
- 2dT. Dale, J. Rebek, J. Am. Chem. Soc. 2006, 128, 4500.
- 3A. J. Russell, J. A. Berberich, G. F. Drevon, R. R. Koepsel, Annu. Rev. Biomed. Eng. 2003, 5, 1.
- 4
- 4aA. L. Jenkins, O. M. Uy, Anal. Commun. 1997, 34, 221;
- 4bA. L. Jenkins, O. M. Uy, G. M. Murray, Anal. Chem. 1999, 71, 373;
- 4cA. L. Jenkins, R. Yin, J. L. Jensen, Analyst 2001, 126, 798;
- 4dC. M. Rudzinski, A. M. Young, D. G. Norcera, J. Am. Chem. Soc. 2002, 124, 1723.
- 5
- 5aH. O. Michel, E. C. Gordon, J. Epstein, Environ. Sci. Technol. 1973, 7, 1045;
- 5bT. J. Novak, L. W. Daasch, J. Epstein, Anal. Chem. 1979, 51, 1271.
- 6
- 6aM. S. Nieuwenhuizen, J. L. N. Harteveld, Sens. Actuators B 1997, 40, 167;
- 6bJ. Negeh-Ngwainbi, P. H. Foley, S. S. Kuan, G. G. Guilbault, J. Am. Chem. Soc. 1986, 108, 5444.
- 7
- 7aK. A. Van Houten, D. C. Heath, R. Pilato, J. Am. Chem. Soc. 1998, 120, 12359;
- 7bS.-W. Zhang, T. M. Swager, J. Am. Chem. Soc. 2003, 125, 3420;
- 7cS. Yamaguchi, I. Yoshimura, T. Kohira, S.-I Tamaru, I. Hamachi, J. Am. Chem. Soc. 2005, 127, 11835.
- 8W. E. Steiner, S. J. Klopsch, W. A. English, B. H. Clowers, H. H. Hill, Anal. Chem. 2005, 77, 4792.
- 9H. Sohn, S. Letant, M. J. Sailor, W. C. Trogler, J. Am. Chem. Soc. 2000, 122, 5399.
- 10
- 10aN. A. Rakow, K. S. Suslick, Nature 2000, 406, 710;
- 10bN. A. Rakow, A. Sen, M. C. Janzen, J. B. Ponder, K. S. Suslick, Angew. Chem. 2005, 117, 4604;
10.1002/ange.200500939 Google ScholarAngew. Chem. Int. Ed. 2005, 44, 4528;
- 10cR. C. Smith, A. G. Tennyson, M. H. Lim, S. J. Lippard, Org. Lett. 2005, 7, 3573.
- 11
- 11aJ.-C. G. Bünzli, C. Piguet, Chem. Soc. Rev. 2005, 34, 1048;
- 11bB. Zhao, X. Y. Chen, P. Cheng, D.-Z. Liao, S.-P. Yan, Z. H. Jiang, J. Am. Chem. Soc. 2004, 126, 15394;
- 11cD. Parker, Coord. Chem. Rev. 2004, 205, 109.
- 12
- 12aS. Lis, J. Alloys Comp. 2002, 341, 45;
- 12bN. Sabbatini, M. Guardigli, J.-M. Lehn, Coord. Chem. Rev. 1993, 123, 201;
- 12cS. W. Magennis, S. Parsons, Z. Pikramenou Chem. Eur. J. 2002, 8, 5761.
10.1002/1521-3765(20021216)8:24<5761::AID-CHEM5761>3.0.CO;2-H CAS PubMed Web of Science® Google Scholar
- 13S. Petoud, J.-C. G. Bünzli, T. Glanzman, C. Piguet, Q. Xiang, P. Thummel, J. Lumin. 1999, 82, 69.
- 14
- 14aJ. B. Beck, S. J. Rowan, J. Am. Chem. Soc. 2003, 125, 13922;
- 14bP. K. Iyer, J. B. Beck, C. Weder, S. J. Rowan, Chem. Commun. 2005, 319;
- 14cD. Knapton, S. J. Rowan, C. Weder, Macromolecules 2006, 39, 651;
- 14dJ. B. Beck, J. M. Ineman, S. J. Rowan Macromolecules 2005, 38, 5060.
- 15It should be noted that ethynylene 1 does not undergo a large degree of self-assembly in solution with the addition of [La(NO3)3]; see the Supporting Information and S. Petoud, J.-C. G. Bünzli, K. J. Schenk, C. Piguet, Inorg. Chem. 1997, 36, 1345.
- 16J. N. Wilson, U. H. F. Bunz, J. Am. Chem. Soc. 2005, 127, 4124.
- 17C. Piguet, J.-C. G. Bünzli, G. Bernardinelli, C. G. Bochet, P. Froidevaux, J. Chem. Soc. Dalton Trans. 1995, 83–96.
- 18A. R. Hopkins, N. S. Lewis, Anal. Chem. 2001, 73, 884.
- 19M. Janotta, M. Karlowatz, F. Vogt, B. Mizaikoff, Anal. Chim. Acta 2003, 496, 339.
- 20A. L. Simonian, T. A. Good, S.-S. Wang, J. R. Wild, Anal. Chim. Acta. 2005, 534, 69.
- 21L. Rotiroti, L. De Stefano, I. Rendina, L. Moretti, A. M. Rossi, A. Piccolo, Biosens. Bioelectron. 2005, 20, 2136.
