Get access

Tetrathiafulvalene-Based Macrocycles Formed by Radical Cation Dimerization: The Role of Intramolecular Hydrogen Bonding and Solvent

Authors

  • Wei-Kun Wang,

    1. Department of Chemistry, Fudan University, 220 Handan Road, Shanghai 200433 (China), Fax: (+86) 21-6564-1740
    Search for more papers by this author
  • Yuan-Yuan Chen,

    1. Department of Chemistry, Fudan University, 220 Handan Road, Shanghai 200433 (China), Fax: (+86) 21-6564-1740
    Search for more papers by this author
  • Dr. Hui Wang,

    Corresponding author
    1. Department of Chemistry, Fudan University, 220 Handan Road, Shanghai 200433 (China), Fax: (+86) 21-6564-1740
    • Hui Wang, Department of Chemistry, Fudan University, 220 Handan Road, Shanghai 200433 (China), Fax: (+86) 21-6564-1740

      Yi Liu, The Molecular Foundry, Lawrence Berkeley National Laboratory, Berkeley, CA 94720 (USA)

      Zhan-Ting Li, Department of Chemistry, Fudan University, 220 Handan Road, Shanghai 200433 (China), Fax: (+86) 21-6564-1740

    Search for more papers by this author
  • Prof. Dr. Dan-Wei Zhang,

    1. Department of Chemistry, Fudan University, 220 Handan Road, Shanghai 200433 (China), Fax: (+86) 21-6564-1740
    Search for more papers by this author
  • Prof. Dr. Yi Liu,

    Corresponding author
    1. The Molecular Foundry, Lawrence Berkeley National Laboratory, Berkeley, CA 94720 (USA)
    • Hui Wang, Department of Chemistry, Fudan University, 220 Handan Road, Shanghai 200433 (China), Fax: (+86) 21-6564-1740

      Yi Liu, The Molecular Foundry, Lawrence Berkeley National Laboratory, Berkeley, CA 94720 (USA)

      Zhan-Ting Li, Department of Chemistry, Fudan University, 220 Handan Road, Shanghai 200433 (China), Fax: (+86) 21-6564-1740

    Search for more papers by this author
  • Prof. Dr. Zhan-Ting Li

    Corresponding author
    1. Department of Chemistry, Fudan University, 220 Handan Road, Shanghai 200433 (China), Fax: (+86) 21-6564-1740
    • Hui Wang, Department of Chemistry, Fudan University, 220 Handan Road, Shanghai 200433 (China), Fax: (+86) 21-6564-1740

      Yi Liu, The Molecular Foundry, Lawrence Berkeley National Laboratory, Berkeley, CA 94720 (USA)

      Zhan-Ting Li, Department of Chemistry, Fudan University, 220 Handan Road, Shanghai 200433 (China), Fax: (+86) 21-6564-1740

    Search for more papers by this author

Abstract

Compounds 1 a and 1 b were prepared by appending two tetrathiafulvalene (TTF) units to an aromatic amide segment that is driven by six or two intramolecular N[BOND]H⋅⋅⋅O hydrogen bonds to adopt a folded conformation. UV/Vis absorption experiments revealed that if the TTF units were oxidized to TTF.+ radical cations, the two compounds could form a stable single molecular noncovalent macrocycle in less polar dichloromethane or dichloroethane or a bimolecular noncovalent macrocycle in a binary mixture of dichloromethane with a more polar solvent owing to remarkably enhanced dimerization of the TTF.+ units. The stability of the (TTF.+)2 dimer was evaluated through UV/Vis absorption, electron paramagnetic resonance, and cyclic voltammetry experiments and also by comparing the results with those of control compound 2. The results showed that introduction of the intramolecular hydrogen bonds played a crucial role in promoting the stability of the (TTF.+)2 dimer and thus the noncovalent macrocyclization of the two backbones in both uni- and bimolecular manners.

Get access to the full text of this article

Ancillary