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Article Dans Une Revue Tetrahedron Année : 2008

Binding studies of tetrathiafulvalene-calix[4]pyrroles with electron-deficient guests

, , , (1) , , , , (1) , , , ,
Kent Nielsen
  • Fonction : Auteur
Luis Martín-Gomis
  • Fonction : Auteur
Ginka-H. Sarova
  • Fonction : Auteur
Lionel Sanguinet
Dustin Gross
  • Fonction : Auteur
Fernando Fernández-Lázaro
  • Fonction : Auteur
Paul-C. Stein
  • Fonction : Auteur
Eric Levillain
Jonathan-L. Sessler
  • Fonction : Auteur
Dirk.-M. Guldi
  • Fonction : Auteur
Ángela Sastre-Santos
  • Fonction : Auteur
Jan Jeppesen
  • Fonction : Auteur


The neutral meso-octamethylporphyrinogen derivative, tetraTTF-calix[4]pyrrole 1 (TTF=tetrathiafulvalene), acts as a multi-faceted receptor in that it interacts with an assortment of different guests in different ways. The conformation of receptor 1 can be reversibly switched between the 1,3-alternate conformation (i.e., 1, Fig. 1) and the cone conformation (i.e., 1·Cl−, Fig. 2) by the repetitive addition of chloride and sodium ions. In this paper, the results of detailed and systematic complexation studies involving both 1 and its chloride-bound complex, 1·Cl−, with a variety of guests are described. Receptor 1 binds quasi-planar nitroaromatic guests in its 1,3-alternate conformation, while release of these guests takes place upon addition of chloride anions. On the other hand, spherical fullerene guests are strongly bound by 1·Cl−. Finally, it was found that a bidentate guest, consisting of a quasi-planar 2,5,7-trinitro-9-dicyanomethylenefluorene moiety tethered to a spherical C60 fullerene, could be recognized by receptor 1 in either its 1,3-alternate or its chloride-bound cone conformation, albeit through very different binding modes.



Dates et versions

hal-03343376 , version 1 (14-09-2021)



Kent Nielsen, Luis Martín-Gomis, Ginka-H. Sarova, Lionel Sanguinet, Dustin Gross, et al.. Binding studies of tetrathiafulvalene-calix[4]pyrroles with electron-deficient guests. Tetrahedron, 2008, 64 (36), pp.8449 - 8463. ⟨10.1016/j.tet.2008.05.141⟩. ⟨hal-03343376⟩
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