We report here the synthesis of chiral bis-porphyrins that have structural features similar to that of the corner of a box. Molecular models suggest the two porphyrin rings should be perpendicular to each other. Thus, the two porphyrins represent two walls of a corner and the pyrrolidine/cyclohexane ring system represents the third wall of a chiral corner. We will report preliminary guest recognition properties of these hosts with non-chiral dicarboxylate-containing species as well as with chiral guests that have three coordinating sites such as amino acids with polar side chains. These types of guests will complement the three recognition sites of the hosts (two metal centers and urea hydrogen bond donors). An initial study with non-chiral dicarboxylates of varying chain length (HO2C-(CH2)n-CO2H, n = 0-10) to determine the optimal distance for simultaneous binding to both metallo centers will be reported. The hosts will then be screened for chiral guest recognition properties of dicarboxylate containing guests and chiral diamines.

Chiral bis-porphyrin hosts: Chiral corners

247th National Meeting (2014)

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