Molecular and ionic complexes of pyrrolidinofullerene bearing chelating 3-pyridyl unitsElectronic supplementary information (ESI) available: Electronic supplementary information (ESI) available: IR spectra of starting compounds and complexes 1, 2 and 4. Crystallographic data in CIF format for complex 1 at 100 and 295R and complex 3 at 120 K. CCDC reference numbers 822362, 822364 and 822366. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c1dt11040c

Molecular and ionic complexes of cis -2,5-di(pyridin-3-yl)pyrrolidino[3,4:1,9](C 60 - I h )[5,6]fullerene DP3FP with chlorobenzene (C 6 H 5 Cl), manganese( ii ) tetraphenylporphyrin (Mn II TPP) and tetrakis(dimethylamino)ethylene (TDAE) have been obtained for the first time. X-ray single crystal structure determination for the crystalline DP3FPC 6 H 5 Cl ( 1 ) solvate proved unambiguously its molecular structure with the cis -arrangement of chelating 3-pyridyl groups. It has been demonstrated that DP3FP easily forms self-assembled photoactive complexes with metallated porphyrins. For example, the formation of a 1:1 complex between DP3FP and zinc ( ii ) tetraphenylporphyrin (Zn II TPP) in cyclohexane solution ( 2 ) was evidenced using absorption spectroscopy. A successful X-ray single crystal structure determination was performed for a self-assembled triad composed of a DP3FP molecule linked with two Mn II TPP molecules in {DP3FP(Mn II TPP) 2 }(C 6 H 4 Cl 2 ) 3 ( 3 ). A strong organic donor TDAE reduces DP3FP to the radical anion state thus forming an ionic complex (TDAE&z.rad; + )(DP3FP&z.rad; )(C 6 H 4 Cl 2 ) 1.6 ( 4 ). Optical, electronic and magnetic properties of 4 were investigated in detail. The performed studies strongly suggest that pyrrolidinofullerene DP3FP can be used as a building block in the design of various organic materials with advanced optoelectronic and/or magnetic properties. Synthesis and characterization of complexes of the fullerene DP3FP with chlorobenzene, manganese( ii ) tetraphenylporphyrin and tetrakis(dimethylamino)ethylene revealed that DP3FP can be used as a building block in organic materials with advanced optoelectronic and/or magnetic properties.