High fidelity self-sorting assembling of meso-cinchomeronimide appended meso-meso linked Zn(II) diporphyrins

In noncoordinating solvents, meso-cinchomeronimide appended Zn(II) porphyrin 2 forms a cyclic trimer, while diporphyrins 7 exhibit high-fidelity self-sorting assembling to form discrete cyclic trimer, tetramer, and pentamer with large association constants from 7_in-in, 7_in-out, and 7_out-out, respectively, through almost perfect discrimination of enantiomeric and conformational differences of the mesocinchomeronimide substituents. In the latter self-sorting processes, the dihedral angles dictated by the two pyridyl nitrogen atoms control the size of the aggregates; the trimer from 7_in-in, the tetarmer from 7_in-out, and the pentamer from 7_out-out. Cyclic structures of (2)₃ and (R-7_out-out)₅ have been determined by single-crystal X-ray diffraction analysis.