Guanosine-based Hydrogen-bonded Scaffolds: Controlling the Assembly of Oligothiophenes

Authors

  • Gian Piero Spada,

    Corresponding author
    1. Alma Mater Studiorum-Università di Bologna Dipartimento di Chimica Organica “A. Mangini” Via San Giacomo 11, 40126 Bologna (Italy)
    • Alma Mater Studiorum-Università di Bologna Dipartimento di Chimica Organica “A. Mangini” Via San Giacomo 11, 40126 Bologna (Italy).
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  • Stefano Lena,

    1. Alma Mater Studiorum-Università di Bologna Dipartimento di Chimica Organica “A. Mangini” Via San Giacomo 11, 40126 Bologna (Italy)
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  • Stefano Masiero,

    1. Alma Mater Studiorum-Università di Bologna Dipartimento di Chimica Organica “A. Mangini” Via San Giacomo 11, 40126 Bologna (Italy)
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  • Silvia Pieraccini,

    1. Alma Mater Studiorum-Università di Bologna Dipartimento di Chimica Organica “A. Mangini” Via San Giacomo 11, 40126 Bologna (Italy)
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  • Mathieu Surin,

    1. ISIS/CNRS UMR 7006 Université Louis Pasteur 8 allée Gaspard Monge, 67000 Strasbourg (France)
    2. Present address: Chimie des Matériaux Nouveaux, Université de Mons–Hainaut, 20, Place du Parc, 7000 Mons, Belgium
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  • Paolo Samorì

    Corresponding author
    1. ISIS/CNRS UMR 7006 Université Louis Pasteur 8 allée Gaspard Monge, 67000 Strasbourg (France)
    2. Istituto per la Sintesi Organica e la Fotoreattività Consiglio Nazionale delle Ricerche via Gobetti 101, 40129 Bologna (Italy)
    • ISIS/CNRS UMR 7006 Université Louis Pasteur 8 allée Gaspard Monge, 67000 Strasbourg (France).
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  • We gratefully acknowledge financial support from the ERA-Chemistry project SurConFold, the EU through the Marie Curie RTNs PRAIRIES (MRTN-CT-2006-035810) and THREADMILL (MRTN-CT-2006- 036040), EST - SUPER (MEST-CT-2004-008128), the ESF-SONS2- SUPRAMATES project, the MiUR/PRIN project 2005035119, the Regione Emilia-Romagna PRIITT Nanofaber Net-Lab. We thank Prof. Roberto Lazzaroni for enlightening discussion about the manuscript. M.S. is Chargé de Recherches of the F.R.S.-FNRS (Belgium). Supporting Information is available online from Wiley InterScience or from the authors.

Abstract

original image

The scaffolding of a π-conjugated oligomer, namely terthiophene, is achieved by taking advantage of the self-assembly of a guanosine derivative into highly directional H-bonded networks. Reversible interconversion allows switching between ribbons and quartet-based assemblies in solution. The self-assembly of 1 on surfaces lead to large lamellae of straight ribbons, ultimately forming 1D conjugated arrays as prototypes of supramolecular nanowires.

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