Octapodal Corannulene Porphyrin-Based Assemblies: Allosteric Behavior in Fullerene Hosting

The Journal of Organic Chemistry
Sergio FerreroCeledonio M Álvarez

Abstract

An octapodal corannulene-based supramolecular system has been prepared by introducing eight corannulene moieties in a porphyrin scaffold. Despite the potential of this double picket fence porphyrin for double-tweezer behavior, NMR titrations show exclusive formation of 1:1 adducts. The system exhibits very strong affinity for C60 and C70 (K1 = (2.71 ± 0.08) × 104 and (2.13 ± 0.1) × 105 M-1, respectively), presenting selectivity for the latter. Density functional theory (DFT) calculations indicate that, in addition to the four corannulene units, the relatively flexible porphyrin tether actively participates in the recognition process, resulting in a strong synergistic effect. This leads to a very strong interaction with C60, which in turn also induces a large structural change on the other face (second potential binding site), leading to a negative allosteric effect. We also introduced Zn2+ in the porphyrin core in an attempt to modulate its flexibility. The resulting metalloporphyrin also displayed single-tweezer behavior, albeit with slightly smaller binding constants for C60 and C70, suggesting that the effect of the coordination of fullerene to one face of our supramolecular platform was still transmitted to the other face, ...Continue Reading

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Citations

Feb 4, 2021·Organic Letters·Dzeneta HalilovicMihaiela C Stuparu
Sep 28, 2021·Chemical Communications : Chem Comm·Adriana Sacristán-MartínCeledonio M Álvarez

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