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A Conjugated Thiophene-Based Rotaxane: Synthesis, Spectroscopy, and Modeling

  1. Leszek Zalewski Dr.1,
  2. Michael Wykes2,
  3. Sergio Brovelli Dr.3,
  4. Massimo Bonini Dr.1,
  5. Thomas Breiner Dr.1,
  6. Marcel Kastler Dr.1,
  7. Florian Dötz Dr.4,
  8. David Beljonne Dr.2,
  9. Harry L. Anderson Prof.5,
  10. Franco Cacialli Prof.3,
  11. Paolo Samorì Prof.6,7

Article first published online: 12 MAR 2010

DOI: 10.1002/chem.200903353

Issue

Chemistry - A European Journal

Chemistry - A European Journal

Volume 16, Issue 13, pages 3933–3941, April 6, 2010

Additional Information

How to Cite

Zalewski, L., Wykes, M., Brovelli, S., Bonini, M., Breiner, T., Kastler, M., Dötz, F., Beljonne, D., Anderson, Harry L., Cacialli, F. and Samorì, P. (2010), A Conjugated Thiophene-Based Rotaxane: Synthesis, Spectroscopy, and Modeling. Chem. Eur. J., 16: 3933–3941. doi: 10.1002/chem.200903353

Author Information

  1. 1

    BASF SE, 67056 Ludwigshafen (Germany)

  2. 2

    Laboratory for Chemistry of Novel Materials, Université de Mons, 20, Place du Parc, 7000 Mons (Belgium)

  3. 3

    Department of Physics and Astronomy (CMMP Group) and London Centre for Nanotechnology, University College London, Gower Street, London (UK)

  4. 4

    BASF SE, Global Research Center Singapore/Organic Electronics, 61 Science Park Road, 117525 (Singapore)

  5. 5

    University of Oxford, Department of Chemistry, Chemistry Research Laboratory, Mansfield Road, Oxford OX1 3TA (UK)

  6. 6

    Nanochemistry Laboratory, ISIS-CNRS 7006, Université de Strasbourg, 8 allée Gaspard Monge, 67000 Strasbourg (France)

  7. 7

    ISOF-CNR, via Gobetti 101, 40129 Bologna (Italy)

Publication History

  1. Issue published online: 26 MAR 2010
  2. Article first published online: 12 MAR 2010
  3. Manuscript Received: 7 DEC 2009

Funded by

  • EC Marie Curie projects. Grant Numbers: MRTN-CT-2006-036040, PITN-CT-2009-238177
  • EC FP7 ONE-P large-scale project. Grant Number: 212311
  • NanoSci-E+ project
  • ESF-SONS2-SUPRAMATES project
  • International Center for Frontier Research in Chemistry
  • FRC
  • Belgian Federal Governement
  • Belgian National Fund for Scientific Research
  • FNRS-FRFC

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Keywords:

  • conjugation;
  • oligothiophenes;
  • optoelectronics;
  • rotaxanes;
  • supramolecular chemistry

Abstract

A dithiophene rotaxane 1⊂β-CD and its shape-persistent corresponding dumbbell 1 were synthesized and fully characterized. 2D NOESY experiments, supported by molecular dynamics calculations, revealed a very mobile macrocycle (β-CD). Steady-state and time-resolved photoluminescence experiments in solution were employed to elucidate the excited-state dynamics for both systems and to explore the effect of cyclodextrin encapsulation. The photoluminescence (PL) spectrum of 1⊂β-CD was found to be blueshifted with respect to the dumbbell 1 (2.81 and 2.78 eV, respectively). Additionally, in contrast to previous observations, neither PL spectra nor the decay kinetics of both threaded and unthreaded systems showed changes upon increasing the concentration or changing the polarity of the solutions, thereby providing evidence for a lack of tendency toward aggregation of the unthreaded backbone.

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