Tapes, Sheets, and Prisms. Identification of the Weak C−F Interactions that Steer Fullerene−Porphyrin Cocrystallization

Abstract

Tetra(pentafluorophenyl)porphyrin (H 2 TPFPP) has been cocrystallized with C 60 from arene solvents to give H 2 TPFPP·C 60, 1, H 2 TPFPP·C 60 ·8Benzene, 3, and 3H 2 TPFPP·2C 60 ·6Toluene, 4 . Their X-ray structures have been determined to identify the supramolecular interactions that lead to tape, sheet, and prismatic packing motifs. In addition to close fullerene−porphyrin π−π interactions, attractive C−F···H−C interactions are important in connecting the C 6 F 5 groups of one porphyrin to the pyrrole positions of a neighbor. This interaction is also seen in the structure of the free-base porphyrin H 2 TPFPP·3 p -Xylene, 2 .