Binding studies of tetrathiafulvalene-calix[4]pyrroles with electron-deficient guests |
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Authors: | Kent A Nielsen Ginka H Sarova Dustin E Gross Paul C Stein Jonathan L Sessler Dirk M Guldi Ángela Sastre-Santos Jan O Jeppesen |
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Institution: | a Department of Physics and Chemistry, University of Southern Denmark, Campusvej 55, DK-5230, Odense M, Denmark b División de Química Orgánica, Instituto de Bioingeniería, Universidad Miguel Hernández, Elche 03202, Alicante, Spain c Institute for Physical and Theoretical Chemistry, Universität Erlangen-Nürnberg, Egerlandstr. 3, 91058 Erlangen, Germany d Université d'Angers, CIMA CNRS, UFR Sciences, 2, bd Lavoisier, 49045 Angers Cedex, France e Department of Chemistry and Biochemistry, The University of Texas at Austin, 1 University Station, A5300, Austin, TX 78712-0165, USA |
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Abstract: | The neutral meso-octamethylporphyrinogen derivative, tetraTTF-calix4]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. |
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Keywords: | Calix[4]pyrroles Supramolecular chemistry Tetrathiafulvalenes Fullerenes Molecular switches |
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