Tweezering the Core of a Dendrimer: A Photophysical and Electrochemical Study†
Vincenzo Balzani Prof. Dr.
Dipartimento di Chimica “G. Ciamician”, Università di Bologna, Via Selmi 2, 40126 Bologna, Italy, Fax: (+39) 051-209-9456
Search for more papers by this authorPaola Ceroni Dr.
Dipartimento di Chimica “G. Ciamician”, Università di Bologna, Via Selmi 2, 40126 Bologna, Italy, Fax: (+39) 051-209-9456
Search for more papers by this authorCarlo Giansante
Dipartimento di Chimica “G. Ciamician”, Università di Bologna, Via Selmi 2, 40126 Bologna, Italy, Fax: (+39) 051-209-9456
Search for more papers by this authorVeronica Vicinelli Dr.
Dipartimento di Chimica “G. Ciamician”, Università di Bologna, Via Selmi 2, 40126 Bologna, Italy, Fax: (+39) 051-209-9456
Search for more papers by this authorFrank-Gerrit Klärner Prof. Dr.
Institut für Organische Chemie, Universität Essen-Duisburg, Campus Essen, Universitätsstrasse 5, 45117 Essen, Germany, Fax: (+49) 201-183-4252
Search for more papers by this authorCarla Verhaelen Dipl.-Chem.
Institut für Organische Chemie, Universität Essen-Duisburg, Campus Essen, Universitätsstrasse 5, 45117 Essen, Germany, Fax: (+49) 201-183-4252
Search for more papers by this authorFritz Vögtle Prof. Dr.
Kekulé-Institut für Organische Chemie und Biochemie, Universität Bonn, Gerhard-Domagk Strasse 1, 53121 Bonn, Germany, Fax: (+49) 228-735-662
Search for more papers by this authorUwe Hahn Dr.
Kekulé-Institut für Organische Chemie und Biochemie, Universität Bonn, Gerhard-Domagk Strasse 1, 53121 Bonn, Germany, Fax: (+49) 228-735-662
Search for more papers by this authorVincenzo Balzani Prof. Dr.
Dipartimento di Chimica “G. Ciamician”, Università di Bologna, Via Selmi 2, 40126 Bologna, Italy, Fax: (+39) 051-209-9456
Search for more papers by this authorPaola Ceroni Dr.
Dipartimento di Chimica “G. Ciamician”, Università di Bologna, Via Selmi 2, 40126 Bologna, Italy, Fax: (+39) 051-209-9456
Search for more papers by this authorCarlo Giansante
Dipartimento di Chimica “G. Ciamician”, Università di Bologna, Via Selmi 2, 40126 Bologna, Italy, Fax: (+39) 051-209-9456
Search for more papers by this authorVeronica Vicinelli Dr.
Dipartimento di Chimica “G. Ciamician”, Università di Bologna, Via Selmi 2, 40126 Bologna, Italy, Fax: (+39) 051-209-9456
Search for more papers by this authorFrank-Gerrit Klärner Prof. Dr.
Institut für Organische Chemie, Universität Essen-Duisburg, Campus Essen, Universitätsstrasse 5, 45117 Essen, Germany, Fax: (+49) 201-183-4252
Search for more papers by this authorCarla Verhaelen Dipl.-Chem.
Institut für Organische Chemie, Universität Essen-Duisburg, Campus Essen, Universitätsstrasse 5, 45117 Essen, Germany, Fax: (+49) 201-183-4252
Search for more papers by this authorFritz Vögtle Prof. Dr.
Kekulé-Institut für Organische Chemie und Biochemie, Universität Bonn, Gerhard-Domagk Strasse 1, 53121 Bonn, Germany, Fax: (+49) 228-735-662
Search for more papers by this authorUwe Hahn Dr.
Kekulé-Institut für Organische Chemie und Biochemie, Universität Bonn, Gerhard-Domagk Strasse 1, 53121 Bonn, Germany, Fax: (+49) 228-735-662
Search for more papers by this authorWe thank Professors Mauro Maestri and Margherita Venturi for useful discussions, and Heinz Bandmann for NMR measurements. This work was supported by the MIUR (Supramolecular Devices Project) and the Deutsche Forschungsgemeinschaft (SFB 452).
Graphical Abstract
Großer Gast – kleiner Wirt: Das Greifen einer molekularen Zange um den Bipyridinium-Kern eines Dendrimers (siehe Bild) wurde fluoreszenzspektroskopisch und elektrochemisch untersucht. Es erwies sich als recht ähnlich den Auffädel-/Abfädelprozessen, die bei Bipyridinium-basierten drahtförmigen Einheiten und ringförmigen Molekülen beobachtet werden.
Supporting Information
Supporting information for this article is available on the WWW under http://www.wiley-vch.de/contents/jc_2001/2005/z501025_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
- 1aG. R. Newkome, C. Moorefield, F. Vögtle, Dendrimers and Dendrons: Concepts, Syntheses, and Perspectives, VCH, Weinheim, 2001;
10.1002/3527600612 Google Scholar
- 1bSpecial issue on Dendrimers and Nanoscience, D. Astruc, C. R. Chim. 2003, 6, 709;
- 1cV. Balzani, P. Ceroni, M. Maestri, C. Saudan, V. Vicinelli, Top. Curr. Chem. 2003, 228, 159;
- 1dJ-P. Majoral, A.-M. Caminade, V. Maraval, Chem. Commun. 2002, 2929;
- 1eS. Hecht, J. M. J. Fréchet, Angew. Chem. 2001, 113, 76;
10.1002/1521-3757(20010105)113:1<76::AID-ANGE76>3.0.CO;2-F Google ScholarAngew. Chem. Int. Ed. 2001, 40, 74;
- 1fM. W. P. L. Baars, E. W. Meijer, Top. Curr. Chem. 2001, 210, 131.
- 2
- 2aB. Alonso, D. Astruc, J.-C. Blais, S. Nlate, S. Rigaut, J. Ruiz, V. Sartor, C. Valério, C. R. Acad. Sci. Ser. IIc 2001, 173;
- 2bL. Liu, R. Breslow, J. Am. Chem. Soc. 2003, 125, 12 110;
- 2cM. F. Ottaviani, S. Jockusch, N. J. Turro, D. A. Tomalia, A. Barbon, Langmuir 2004, 20, 10 238.
- 3
- 3aP. A. Chase, R. J. M. K. Gebbink, G. van Koten, J. Organomet. Chem. 2004, 689, 4016;
- 3bD. Astruc, Pure Appl. Chem. 2003, 75, 461;
- 3cF. Diederich, B. Felber, Proc. Natl. Acad. Sci. USA 2002, 99, 4778;
- 3dA. Juris, M. Venturi, P. Ceroni, V. Balzani, S. Campagna, S. Serroni, Collect. Czech. Chem. Commun. 2001, 66, 1;
- 3eC. B. Gorman, J. C. Smith, Acc. Chem. Res. 2001, 34, 60;
- 3fI. Cuadrado, M. Morán, C. M. Casado, B. Alonso, J. Losada, Coord. Chem. Rev. 1999, 193–195, 395.
- 4
- 4aH. D. Abruña, Anal. Chem. 2004, 76, 310A;
- 4bM.-C. Daniel, F. Ba, J. A. Ruiz, D. Astruc, Inorg. Chem. 2004, 43, 8649;
- 4cB. Alonso, C. M. Casado, I. Cuadrado, M. Morán, A. E. Kaifer, Chem. Commun. 2002, 1778.
- 5C. M. Cardona, S. Mendoza, A. E. Kaifer, Chem. Soc. Rev. 2000, 29, 37.
- 6
- 6aT. L. Chasse, C. B. Gorman, Langmuir 2004, 20, 8792;
- 6bF. Marchioni, M. Venturi, P. Ceroni, V. Balzani, M. Belohradsky, A. M. Elizarov, H.-R. Tseng, J. F. Stoddart, Chem. Eur. J. 2004, 10, 6361;
- 6cN. D. McClenahan, R. Passalacqua, F. Loiseau, S. Campagna, B. Verheyde, A. Hameurlaine, W. Dehaen, J. Am. Chem. Soc. 2003, 125, 5356;
- 6dY. Rio, G. Accorsi, N. Armaroli, D. Felder, E. Levillain, J.-F. Nierengarten, Chem. Commun. 2002, 2830;
- 6eP. J. Dandliker, F. Diederich, M. Gross, C. B. Knobler, A. Louati, Angew. Chem. 1994, 106, 1821; Angew. Chem. Int. Ed. Engl. 1994, 33, 1739.
- 7W. Ong, M. Gomez-Kaifer, A. E. Kaifer, Chem. Commun. 2004, 1677.
- 8H. W. Gibson, N. Yamaguchi, L. Hamilton, J. W. Jones, J. Am. Chem. Soc. 2002, 124, 4653.
- 9K. J. C. van Bommel, G. A. Metselaar, W. Verboom, D. N. Reinhoudt, J. Org. Chem. 2001, 66, 5405.
- 10J. W. Lee, Y. H. Ko, S.-H. Park, K. Yamaguchi, K. Kim, Angew. Chem. 2001, 113, 769;
Angew. Chem. Int. Ed. 2001, 40, 746.
10.1002/1521-3773(20010216)40:4<746::AID-ANIE7460>3.0.CO;2-P CAS PubMed Web of Science® Google Scholar
- 11
- 11aW. Ong, J. Grindstaff, D. Sobransingh, R. Toba, J. M. Quintela, C. Peinador, A. E. Kaifer, J. Am. Chem. Soc. 2005, 127, 3353;
- 11bM. Moon, J. Grindstaff, D. Sobransingh, A. E. Kaifer, Angew. Chem. 2004, 116, 5612;
10.1002/ange.200460179 Google ScholarAngew. Chem. Int. Ed. 2004, 43, 5496;
- 11cW. Ong, A. E. Kaifer, Angew. Chem. 2003, 115, 2214; Angew. Chem. Int. Ed. 2003, 42, 2164;
- 11dR. Toba, J. M. Quintela, C. Peinador, E. Román, A. E. Kaifer, Chem. Commun. 2002, 1768;
- 11eC. M. Cardona, T. D. McCarley, A. E. Kaifer, J. Org. Chem. 2000, 65, 1857.
- 12For a somewhat related gas-phase study of these systems, see: C. A. Schalley, C. Verhaelen, F.-G. Klärner, U. Hahn, F. Vögtle, Angew. Chem. 2005, 117, 481;
10.1002/ange.200461872 Google ScholarAngew. Chem. Int. Ed. 2005, 44, 477.
- 13
- 13aF.-G. Klärner, B. Kahlert, Acc. Chem. Res. 2003, 36, 919;
- 13bF. Marchioni, A. Juris, M. Lobert, U. P. Seelbach, B. Kahlert, F.-G. Klärner, New J. Chem. in press.
- 14F.-G. Klärner, U. Burkert, M. Kamieth, R. Boese, J. Phys. Org. Chem. 2000, 13, 604.
- 15P. Ceroni, V. Vicinelli, M. Maestri, V. Balzani, W. M. Müller, U. Müller, U. Hahn, F. Osswald, F. Vögtle, New J. Chem. 2001, 25, 989.
- 16D. B. Amabilino, M. Asakawa, P. R. Ashton, R. Ballardini, V. Balzani, M. Belohradsky, A. Credi, M. Higuchi, F. M. Raymo, T. Shimizu, J. F. Stoddart, M. Venturi, K. Yase, New J. Chem. 1998, 22, 959.
- 17J. N. Demas, G. A. Crosby, J. Phys. Chem. 1971, 75, 991.
- 18I. B. Berlman, Handbook of Fluorescence Spectra of Aromatic Molecules, 2nd ed., Academic Press, New York, 1971.
- 19R. Toba, J. M. Quintela, C. Peinador, E. Roman, A. E. Kaifer, Chem. Commun. 2001, 857.
- 20A. Credi, L. Prodi, Spectrochim. Acta Part A 1998, 54, 159.
- 21V. Balzani, A. Credi, M. Venturi, Molecular Devices and Machines, A Journey into the Nano World, Wiley-VCH, Weinheim, 2003.
10.1002/3527601600 Google Scholar
Citing Literature
This is the
German version
of Angewandte Chemie.
Note for articles published since 1962:
Do not cite this version alone.
Take me to the International Edition version with citable page numbers, DOI, and citation export.
We apologize for the inconvenience.
