High Fidelity Self-Sorting Assembling of <i>m</i><i>eso</i>-Cinchomeronimide Appended <i>m</i><i>eso-meso</i> 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 7in-in, 7in-out, and 7out-out, respectively, through almost perfect discrimination of enantiomeric and conformational differences of the meso-cinchomeronimide 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 7in-in, the tetarmer from 7in-out, and the pentamer from 7out-out. Cyclic structures of (2)3 and (R-7out-out)5 have been determined by single-crystal X-ray diffraction analysis.