Mono‐Tetrathiafulvalene Calix[4]pyrrole in the Electrochemical Sensing of Anions
2003; Wiley; Volume: 42; Issue: 2 Linguagem: Inglês
10.1002/anie.200390074
ISSN1521-3773
AutoresKent A. Nielsen, Jan O. Jeppesen, Eric Levillain, Jan Becher,
Tópico(s)Luminescence and Fluorescent Materials
ResumoAngewandte Chemie International EditionVolume 42, Issue 2 p. 187-191 Communication Mono-Tetrathiafulvalene Calix[4]pyrrole in the Electrochemical Sensing of Anions† Kent A. Nielsen, Kent A. Nielsen Department of Chemistry Odense University (University of Southern Denmark) Campusvej 55, 5230 Odense M, Denmark, Fax: (+45) 66-158-780Search for more papers by this authorJan O. Jeppesen Dr., Jan O. Jeppesen Dr. [email protected] Department of Chemistry Odense University (University of Southern Denmark) Campusvej 55, 5230 Odense M, Denmark, Fax: (+45) 66-158-780Search for more papers by this authorEric Levillain Dr., Eric Levillain Dr. Ingénierie Moléculaire et Matériaux Organiques CNRS UMR 6501, Université d'Angers 2 Bd Lavoisier, 49045 Angers, FranceSearch for more papers by this authorJan Becher Prof., Jan Becher Prof. [email protected] Department of Chemistry Odense University (University of Southern Denmark) Campusvej 55, 5230 Odense M, Denmark, Fax: (+45) 66-158-780Search for more papers by this author Kent A. Nielsen, Kent A. Nielsen Department of Chemistry Odense University (University of Southern Denmark) Campusvej 55, 5230 Odense M, Denmark, Fax: (+45) 66-158-780Search for more papers by this authorJan O. Jeppesen Dr., Jan O. Jeppesen Dr. [email protected] Department of Chemistry Odense University (University of Southern Denmark) Campusvej 55, 5230 Odense M, Denmark, Fax: (+45) 66-158-780Search for more papers by this authorEric Levillain Dr., Eric Levillain Dr. Ingénierie Moléculaire et Matériaux Organiques CNRS UMR 6501, Université d'Angers 2 Bd Lavoisier, 49045 Angers, FranceSearch for more papers by this authorJan Becher Prof., Jan Becher Prof. [email protected] Department of Chemistry Odense University (University of Southern Denmark) Campusvej 55, 5230 Odense M, Denmark, Fax: (+45) 66-158-780Search for more papers by this author First published: 16 January 2003 https://doi.org/10.1002/anie.200390074Citations: 109 † We gratefully acknowledge the University of Odense for a Ph.D scholarship to K.A.N., financial support from Carlsbergfondet to J.O.J, and the French Embassy Copenhagen for a travel grant to J.B. Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onEmailFacebookTwitterLinkedInRedditWechat Graphical Abstract A redox-responsive receptor based on the annulation of the calix[4]pyrrole-receptor unit and the redox-active tetrathiafulvalene transducer unit is able to bind anions (see scheme) and act as an efficient chemosensor for the detection of anions by electrochemical means. References 1 1aJ.-M. Lehn, Supramolecular Chemistry, VCH, Weinheim, 1995; 1b Comprehensive Supramolecular Chemistry, Vol. 1–11 (Ed ), Pergamon, Oxford, 1996. 2 2aP. L. 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Sessler, Angew. Chem. 2000, 112, 1847–1850; Angew. Chem. Int. Ed. 2000, 39, 1777–1780. 7J. L. Sessler, P. A. Gale, J. W. Genge, Chem. Eur. J. 1998, 4, 1095–1099. 8 8aJ. L. Sessler, A. Gebauer, P. A. Gale, Gazz. Chim. Ital. 1997, 127, 723–726; 8bP. A. Gale, M. B. Hursthouse, M. E. Light, J. L. Sessler, C. N. Warriner, R. S. Zimmerman, Tetrahedron Lett. 2001, 42, 6759–6762. 9For recent TTF reviews, see: 9aM. R. Bryce, J. Mater. Chem. 2000, 10, 589–598; 9bM. B. Nielsen, C. Lomholt, J. Becher, Chem. Soc. Rev. 2000, 29, 153–164; 9cJ. L. Segura, N. Martín, Angew. Chem. 2001, 113, 1416–1455; Angew. Chem. Int. Ed. 2001, 40, 1372–1409. 10 10aJ. O. Jeppesen, J. Perkins, J. Becher, J. F. Stoddart, Org. Lett. 2000, 2, 3547–3550; 10bJ. O. Jeppesen, J. Perkins, J. Becher, J. F. Stoddart, Angew. Chem. 2001, 113, 1256–1261; Angew. Chem. Int. Ed. 2001, 40, 1216–1221; 10cC. P. Collier, J. O. Jeppesen, Y. Luo, J. Perkins, E. W. Wong, J. R. Heath, J. F. Stoddart, J. Am. Chem. 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Chem. 2000, 65, 5794–5805. 13C. Bucher, R. S. Zimmerman, V. Lynch, J. L. Sessler, J. Am. Chem. Soc. 2001, 123, 9716–9717. 14More than 20 % of 3 can be recovered during chromatographic purification. 15H. Tsukube, H. Furuta, A. Odani, Y. Takeda, Y. Kudo, Y. Inoue, Y. Liu, H. Sakamoto, K. Kimura in Comprehensive Supramolecular Chemistry, Vol. 8 (Ed ), Pergamon, Oxford, 1996, pp. 425–482. 16P. Anzenbacher, Jr.,K. Jursýková, J. L. Sessler, J. Am. Chem. Soc. 2000, 122, 9350–9351. 17M. J. Hynes, J. Chem. Soc. Dalton Trans. 1993, 311–312. 18 18aJ. A. A. de Boer, D. N. Reinhoudt, J. Am. Chem. Soc. 1985, 107, 5347–5351; 18bL. Fielding, Tetrahedron 2000, 56, 6151–6170. 19Similar results have been observed with Cl− ions. 20CV titration experiments were also carried out with solutions containing F− ions. However, it was not possible to obtain a ΔE value for the 4⋅F− complex, because the redox events become irreversible. This may be caused by the formation of a NF bond at the doped state, by delocalization of the positive charge from TTF+., or by oxidation of the calix[4]pyrrole skeleton. This phenomena has previously been observed, see ref. [8]. 21The control experiments carried out by means of the titration of 3 with solutions containing Br− ions did not show any observable displacement of the first oxidation potential. 22The character of the highest-occupied molecular orbital (HOMO) of monopyrrolo TTFs has recently been calculated and shows that approximately 13 % of the HOMO density is located on the outer pyrrole ring, see ref. [12b]. 23P. A. Gale, J. L. Sessler, V. Král, V. Lynch, J. Am. Chem. Soc. 1996, 118, 5140–5141. 24Binding constants between meso-octamethylcalix[4]pyrrole and Cl−, and F− ions in CD3CN/0.5 % v/v D2O at 295 K have been determined by 1H NMR spectroscopy to be 5.0×103 M−1 and >1.0×104 M−1, respectively, see ref. [5a]. However, calorimetric measurements carried out in anhydrous MeCN (<10 ppm) on meso-octamethylcalix[4]pyrrole gave binding constants of 1.9×105 M−1 and 1.5×105 M−1 for Cl−, and F− ions, respectively, see ref. [5b]. 25To minimize adsorption phenomena, a high scan rate of 0.5 V s−1 was used. Citing Literature Volume42, Issue2January 13, 2003Pages 187-191 ReferencesRelatedInformation
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