Theoretical investigation of the stacking interactions between curved conjugated systems and their interaction with fullerenes

Herein, we perform a M06-2X/6-311G investigation of the homo and mixed dimers formed between corannulene, sumanene, and pentaindenocorannulene; also, their complexes with C-60 and C-70 were studied. Despite the lower area of sumanene, the interaction of the sumanene-dimer is stronger that of the corannulene-dimer because of CH-pi interactions. For mixed-dimers, when the concave and convex sides perfectly match the interactions are similar to those of the homodimers. However, when the concave area is larger than the convex one, CH-pi interactions become important and perfect stacking is lost. The interaction between pentaindenocorannulene-C-60 is twice that of corannulene-C-60, and Delta G(298) = -10.8 kcal/mol. Thus, pentaindenocorannulene is a better choice to catch C-60. (C) 2011 Elsevier B.V. All rights reserved.