Bis-corannulene Receptors for Fullerenes Based on Klärner's Tethers: Reaching the Affinity Limits.
Bis-corannulene receptors 4 and 5 with Klärner's tethers prepared by the Diels-Alder cycloaddition form inclusion complexes with C60 and C70, as evidenced by (1)H NMR titration. While 4 exhibits affinity toward fullerenes comparable to the previously reported corannulene-based receptors, 5 exceeds the performance of the former systems by ca. 2 orders of magnitude and, in addition, shows an enhanced preference for C70 over C60. The X-ray crystal structure of C60@5 and DFT calculations indicate that the tether in 5 not only preorganizes the pincers into a proper topology of the host but also contributes to the dispersion-based binding with the fullerene guests.
Department of Chemistry, Mississippi State University , Mississippi State, Mississippi 39762, United States.
Peumie L
PL
Abeyratne Kuragama
Department of Chemistry, Louisiana State University , Baton Rouge, Louisiana 70803, United States.
Frank R
FR
Fronczek
Department of Chemistry, Mississippi State University , Mississippi State, Mississippi 39762, United States.
Andrzej
A
Sygula
D018360:Crystallography, X-Ray; D061565:Cycloaddition Reaction; D037741:Fullerenes / Q000737:chemistry* / Q000378:metabolism; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D008968:Molecular Conformation; D015394:Molecular Structure; D011084:Polycyclic Aromatic Hydrocarbons / Q000737:chemistry*; D011166:Porphyrins / Q000737:chemistry
D037741:Fullerenes; D011084:Polycyclic Aromatic Hydrocarbons; D011166:Porphyrins; C434863:corannulene