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Group F. Vögtle, Kekulé-Institut, Uni versität Bonn, Germany

LIMM:. Light-Induced Molecular Movements Photo-Gated Devices. Evaluation Meeting, Kork, 22.-25.6.03. Group F. Vögtle, Kekulé-Institut, Uni versität Bonn, Germany. Dansylated Dendrimers (luminescent). G. 2. G. 1. 6. 0. %. 9. 0. %. G. 3. 6. 0. %. G. 4. 4. 9. %.

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Group F. Vögtle, Kekulé-Institut, Uni versität Bonn, Germany

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  1. LIMM: Light-Induced Molecular Movements Photo-Gated Devices Evaluation Meeting, Kork, 22.-25.6.03 Group F. Vögtle, Kekulé-Institut, Uni versität Bonn, Germany

  2. Dansylated Dendrimers(luminescent)... G 2 G 1 6 0 % 9 0 % G 3 6 0 % G 4 4 9 % (not planar) POPAM A. Archut, S. Gestermann, R. Hesse, C. Kauffmann, F. Vögtle, Synlett,1998, 5, 546-548.

  3. Convergent Synthesis O O O O O O O O O O O O O O S O O O S O O O O O O O O O S S O O O O O O O O O O O O S S O O O O O O O O O O S O O S O O O O O O O O O O O O O O Mix-Type-Dendrimer N N N N N N N N N N N N N Divergent Synthesis N A. Archut, S. Gestermann, R. Hesse, C. Kauffmann, F. Vögtle, Synlett,1998, 5, 546-548. (Kim, Shinkai)

  4. Molecular Switches trans-Azobenzenzecis-Azobenzenze (linear, no dipole moment)(bent, dipole moment 3,5 D)

  5. O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O N N O O O O O O O O O O O O N O O N O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O T. Aida et al., Nature 1997, 388, 454. O O O O O O O O O O O O O O O O O O O O O O O O N O O O O O N O O O O O O O O O dark trans hn O O N C H N H 1 0 2 0 cis N O C H (First Crown-type Azo-switches: S. Shinkai et al., J. Amer. Chem. Soc.1980, 102, 5860.) Photoresponsive PAMAM dendritic architecture: Banthia et al.,Tetrahedron Letters2001,42,501. 6 1 3 4, 8, 16, 32, 64 Recent Overview: O.Villavicencio, D.V. McGrath, Azobenzene-containing Dendrimers, Adv. In Dendrit. Macromol.2002, 5, 1-44. McGrath et al., Chem. Commun.1997, 857; cf. JACS1999, 121, 4912. E. W. Meijer et al., J. Am. Chem. Soc.1998, 120, 8199. Photoresponsive-functionalized Dendrimers F. Vögtle et al., Chem. Ber. 1993, 126, 1161-1169. A. Archut,F. Vögtle, inH.S. Nalwa (ed.), Handbook of Nanostructured Materials and Nanotechnology, Vol. 5: Organics, Polymers, and Biological Materials, Academic Press 2000, 333-374, Dendritic Molecules - Historic Development

  6. Circumrotation Azobenzene-Based Photoswitchable Catenanes F. Vögtle et al., Liebigs Ann.1995, 649-656.

  7. Rotaxanes with Chiral Stoppers and Photoresponsive Central Unit Mechanical Frequency Doubling? C. Kauffmann, W. M. Müller, F. Vögtle, S. Weinmann, S. Abramson, B. Fuchs, Synthesis1999, 5, 849-853.

  8. N N N N N N N N 313 nm N N N N N N N O N N H N H O O N N H N H N O O N H N H O O N N N H N H N N N O O N H N N N H N N N O O N H N N N N N H N N O O H N N N N H N N N N O O N N N N H N N H N N O N N N N O N H H N O N N N N N N O N N N N H N N H O O N N H N N N N N N H N O N O N N H N N H O N N O N N N H N N H N O O H N H N N O N O H N H N N O O N H N H N O N N N N N N N N N N N N N N Azobenzene-Functionalized Covalent Dendrimers (E)-config. G4 F. Vögtle et al., L. De Cola, V. Balzani et al., J. Am. Chem. Soc.1998, 120, 12187-12191. F. Vögtle et al., Liebigs Ann.1995, 649-656; F. Vögtle et al., Angew. Chem. Int. Ed. Engl.1993, 32, 1295; K. Rissanen, F. Vögtle et al., Liebigs Ann.1995, 649-656; First crown-type azobenzene switches: S. Shinkai, O. Manabe, Top. Curr. Chem.1984,121, 67 .

  9. Holographic Films from Photo-Switchable Dendrimers => (like polymer), even if low mol. mass A. Archut, F. Vögtle,* L. De Cola, G. C. Azzelini, V. Balzani,* P.S. Ramanujam, R. H. Berg, Chem. Eur. J. 1998, 4, 699-706.

  10. Two Chromophores Reference compounds: V. Balzani, P. Ceroni, M. Maestri, F. Vögtle, M.Gorka, Photochem. Photobiol. Scii. 2002, 1, 45-51; P. Ceroni, I. Laghi, M. Maestri, V. Balzani, S. Gestermann, M. Gorka, F. Vögtle, ibid. 2002. 26, 66-75.

  11. Fluorescence quenched by trans-azobenzene units (EnT) and by tert-amine of POPAM (ET) O O P O P A M S N N N n Two Chromophores interacting trans/cis Photoisomerization t 1/2 Model Cpds.: Dendrimer favors trans (Steric effect at the periphery?) F. Vögtle, M.Gorka, R. Hesse, P. Ceroni, M. Maestri, V. Balzani, Photochem. Photobiol. Sci. 2002, 1, 45-51; P. Ceroni, I. Laghi, M. Maestri, V. Balzani, S. Gestermann, M. Gorka, F. Vögtle, ibid. 2002,26, 66-75.

  12. N N N N N N N N N N N N N N N N N N N N N N O O N S S O O O O N S N O S N O O H N N H N O O S N H N H N S N O O H N N H O N S S N O O N H H N N O N N O S N S N O N H N N N N H O N O N O N S N S N O H N H N N O N N N O N O N S N S N N O N O H H N N N N N O O N H H N S N N N S O N N O N N N N O O S N N N S H N N H O O N N N N N H H O N O N N S N N S N O O N N N O N N H H N O N S N S N O N O N N O H N N N H N O N S S N O N N O N N H H N O N O S S N O H N N H O O N N S N H H N S O O N H N N H O O N S O N S N O O O O S S N O O N N N N N N N N N N N N N N N N N N N N N N Photoswitchable and pH-sensitive Dendrimers (Generation 0- 5) Dabsyl- POPAM H+ G 4 => dendritic sponges A. Dirksen, E. Zuidema, R.M. Williams, L. De Cola, C. Kauffmann, F. Vögtle, A. Roque, F. Pina, Macromolecules2002, 35, 2743-2747.

  13. 1.pH 9 (basic) pH 2 (acidic) 2.time Methyl Orange Dendrimers as pH-Indicator (hours) => pH- and photosensitive Dendritic effect A. Dirksen, E. Zuidema, R.M. Williams, L. De Cola, C. Kauffmann, F. Vögtle, A. Roque, F. Pina, Macromolecules2002, 35, 2743-2747.

  14. HPLC Vögtle-group 2003

  15. LIMM Ferrara 7.2.2003

  16. LIMM Bonn 4.4.2003 * * *

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