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

• Published in: Chemical science (Cambridge) Vol. 13; no. 44; pp. 13147 - 13152
• Main Authors: Kato, Kenichi, Ohtani, Shunsuke, Gon, Masayuki, Tanaka, Kazuo, Ogoshi, Tomoki
• Format: Journal Article
• Language: English
• Published: CAMBRIDGE Royal Soc Chemistry 16.11.2022; Royal Society of Chemistry; The Royal Society of Chemistry
• Subjects: Chemistry; Chemistry, Multidisciplinary; Chromophores; Physical Sciences; Pyrenes; Science & Technology; CIRCULARLY-POLARIZED LUMINESCENCE; HOST; DICHROISM; DIPOLE-MOMENTS; MOLECULES
• ISSN: 2041-6520; 2041-6539
• DOI: 10.1039/d2sc04168e

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. Chirality of a C 5 -symmetric pillar[5]arene was effectively transmitted to pyrene arrays in hybrid molecules. The pyrenes showed achiral monomer fluorescence and circularly polarized excimer emission.