Hemicarceplexes Modify the Solubility and Reduction Potentials of C₆₀

Abstract

A highly stable C60-incarcerated hemicarceplex, which retains its molecular integrity after heating at 523 K in air for at least 3 h, significantly increases the solubility of C60 in nonpolar solvents and increases the reduction potentials of the entrapped fullerene. Modification with [(η(5)-C5Me5)Ru(II)](+) dramatically increases the solubility of this hemicarceplex in polar, protic solvents (e.g., MeOH).

Recent advances in supramolecular fullerene chemistry

“…For instance, encapsulated fullerenes can exhibit improved solubility, (radical) stability, catalytic activity or modulated redox potentials. [293][294][295] As discussed in section 2, encapsulated fullerenes can also undergo itero-, regioand stereoselective addition reactions. 52,296,297 The selective encapsulation of fullerenes is of interest for obtaining pure fullerenes from complex mixtures (e.g.…”

Are the Physical Properties of Xe@Cryptophane Complexes Easily Predictable? The Case of syn- and anti-Tris-aza-Cryptophanes

“…For example, ring-closing reactions leading to the formation of two cyclotribenzylene (CTB) units are the main limitation, as the electron-donating substituents must be grafted onto the benzene rings for the reaction to be successful. Thus, for this reason, the overwhelming majority of cryptophane derivatives reported in literature have been prepared with vanillyl alcohol as a starting material, a molecule that contains two oxygen atoms grafted onto a benzene ring . Despite the difficulties in preparing novel cryptophane structures decorated with heteroatoms, the synthesis of sulfur-containing cryptophanes has been reported by Hardie et al and Chambron et al via the direct-coupling method .…”

Stabilization of reactive species by supramolecular encapsulation

“…For the sake of brevity, examples related to the stabilization of high-energy conformers, [27][28][29][30][31] geometrical isomers, 32 tautomers, [33][34][35] unusual metal oxidation/spin states, [36][37][38] or non-covalently bonded aggregates 39,40 will not be discussed. Likewise, the use of reversible molecular encapsulation as a tool for the selective functionalization [11][12][13][41][42][43][44][45][46] of stable chemical entities and in the catalysis of chemical reactions [8][9][10] will not be reviewed.…”