Cyclic arrays of five pyrenes on one rim of a planar chiral pillar[5]arene

Abstract

Spatial arrangement of multiple planar chromophores is an emerging strategy for molecule-based chiroptical materials via easy and systematic synthesis. We attached five pyrene planes to a chiral macrocycle, pillar[5]arene, producing a set of chiroptical molecules in which pyrene-derived absorption and emission were endowed with dissymmetry by effective transfer of chiral information. The chiroptical response was dependent on linker structures and substituted patterns because of variable interactions between pyrene units. One of these hybrids showed larger dissymmetry factor and response wavelength (g_lum = 7.0 × 10⁻³ at ca. 547 nm) than reported pillar[5]arene-based molecules using the pillar[5]arene cores as parts of photo-responsive π-conjugated units.