A boron dipyrromethene chiral at boron and carbon with a bent geometry: synthesis, resolution and chiroptical properties. Issue 51 (7th June 2022)

• Record Type: Journal Article
• Authors: Işık, Murat; Dündar, Esra; Şahin, Ertan; Tanyeli, Cihangir
• Is Part Of: Chemical communications. Volume 58:Issue 51(2022)
• Page Start: 7188
• Page End: 7191
• Publication Date: 2022-06-07
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1039/d2cc02179j
• Languages: English
• ISSNs: 1359-7345

Abstract

Abstract : We report a boron dipyrromethene that is chiral at boron and carbon (B*C*-BODIPY) and accessible through a two-pot, one-step synthesis—an interrupted Knoevenagel condensation. Abstract : We report a boron dipyrromethene that is chiral at boron and carbon (B*C*-BODIPY) and accessible through a two-pot, one-step synthesis—an interrupted Knoevenagel condensation. The electronic circular dichroism spectra of chiral high performance liquid chromatography-resolved enantiomers show clear Cotton effects (∣ g abs ∣ ∼ 2.0 × 10 −4 ) in the visible region, suggesting efficient chirality induction to the otherwise achiral BODIPY. The dye's unusually weak fluorescence ( Φ fl < 0.01) is attributed partly to vibrational relaxations, as revealed by viscosity experiments, and partly to probable intersystem crossing that may be facilitated by the reduced symmetry of the bent-shaped molecular geometry.