Chiral pyrrolidine-porphyrin hybrids: Prediction of enantio preference in guest binding a priori based on host design

Here I report the synthesis and chiral recognition properties of several porphyrin hosts with introverted functionality. The hosts are hybrids of tetra phenyl zinc porphyrin and chiral pyrrolidines. The chiral recognition properties of the porphyrin hosts with chiral carboxylate containing guests are described. UV/Vis and 1H-NMR spectroscopic results indicate that urea functionalized hosts shows enantiopreference in binding mandelate tetrabutyl ammonium salt stereoisomers. We can predict which stereoisomer of a guest will preferentially bind to these hosts using a simple binding model.