Synthesis and spectroscopic properties of chiral bornane[2,3-b]pyrazino-fused [30]trithiadodecaazahexaphyrins

Abstract

First chiral bornane[2,3-b]pyrazino-fused [30]trithiadodecaazahexaphyrins were prepared by a crossover condensation of R-(+)- or S-(–)-bornane[2′,3′-b]-2,3-dicyanopyrazine and 2,5-diamino-1,3,4-thiadiazole using two different methods. R-(+)- and S-(–)-enantiomers were characterized by their optical rotations and circular dichroism spectra, showing a mirror image relationship with respect to [θ] = 0. Regioisomers with C1 and C3 symmetry of R-(+)-[30]trithiadodecaazahexaphyrin have been separated using HPLC CHIRALPACK IC analytical column, allowing their unambiguous identification and characterization.