Double‐stranded ladderphanes with C2‐symmetric planar chiral ferrocene linkers

Abstract

ABSTRACTEight ladderphanes with C2‐symmetric planar chiral ferrocene linkers are synthesized by ring opening metathesis polymerization of bisnorbornene monomers using Grubbs‐I catalyst. The aminobenzoate in both monomers and polymers shows absorption maximum around 320 nm. Both monomers and polymers are Circular dichroism (CD) active. Little enhancements of CD profiles around 320 nm are observed for ladderphanes having chiral chloro‐ or phenyl‐substituted ferrocene linkers. However, ladderphanes with a phenyl substituent on the cyclopendienyl ring exhibits enhancement of CD curves aound 240–300 nm. The congested phenyl moieties in adjacent linkers in this polymer might be well oriented such that interactions between these aromatic substituents on different monomeric units might provoke the enhancement of the CD curves in this region. When the methyl‐substituted cyclopendienyl ligand is used for chiral ferrocene linkers, the ladderphanes exhibit two‐fold enhancement of CD spectrum around 320 nm. This enhancement is further increased when the cyclopentadienyl ligand contains an additional phenyl substituent, owing to exciton coupling between aminobenzoate moieties in adjacent monomeric units. Moreover, the intensity of the CD curves in the region of 240–300 nm is significantly increased. These results suggest that the later polymer may adopt a posible helical structure. © 2017 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2017, 55, 2999–3010