Contorted polycyclic aromatic molecules, such as corannulenes and sumanenes, have been studied as host molecules for fullerenes due to their complementary geometries. It has been suggested that stronger associations with fullerenes can be attained by extending their π surface or by incorporating heteroatoms, as unsubstituted corannulene and sumanene do not readily complex with fullerenes in solution. Here, we design and synthesize π-extended buckybowls derived from contorted hexabenzocoronene and pentabenzocoronene with either pentyl or butoxy side chains. These coronene-based buckybowls have approximately twice the π surface compared to unsubstituted corannulene and sumanene. Buckybowls with pentyl side chains complex with C60 in a preferred 1:1 buckybowl-to-C60 stoichiometry, with association constants on the order of 103 M-1. Complexation with C60 further strengthens with the addition of heteroatoms in buckybowls bearing butoxy side chains. We find a preferred 1:2 association stoichiometry with fullerene and association constants on the order of 104 M-1. Density functional theory calculations suggest the larger dipole moment on the butoxy-substituted buckybowls relative to their pentyl-substituted counterparts is responsible.
All Science Journal Classification (ASJC) codes
- Chemical Engineering(all)
- Materials Chemistry