Supramolecular immobilization of fullerenes on gold surfaces:: receptors based on calix[n]arenes, cyclotriveratrylene (CTV) and porphyrins

To explore their ability to immobilize C-60 non-covalently on gold surfaces, a series of thioctic esters derived from calix[n] arene, porphyrin and cyclotriveratrylene (CTV) have been prepared. Well-characterized self-assembled monolayers (SAMs) of these compounds were used to incorporate [60]fullerene onto gold surfaces. SAMs of CTV derivatives 7 and 8, calix[8]arene derivative 6 and porphyrin derivatives 9 and 10 are reasonably effective at immobilizing C-60 on the surfaces, while calix[4]arene derivatives 1-4 and calix[6]crown-4 derivative 5 are not. However, the latter exhibit interesting metal cation and aromatics amine recognition properties, respectively.