A boron dipyrromethene chiral at boron and carbon with a bent geometry: synthesis, resolution and chiroptical properties


Işık M., DÜNDAR E., ŞAHİN E., TANYELİ C.

Chemical Communications, vol.58, no.51, pp.7188-7191, 2022 (Peer-Reviewed Journal) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 58 Issue: 51
  • Publication Date: 2022
  • Doi Number: 10.1039/d2cc02179j
  • Journal Name: Chemical Communications
  • Journal Indexes: Science Citation Index Expanded, Scopus, Academic Search Premier, Chemical Abstracts Core, Chimica, Communication Abstracts, Compendex, EMBASE, MEDLINE, DIALNET, Index Chemicus (IC)
  • Page Numbers: pp.7188-7191

Abstract

© 2022 The Royal Society of Chemistry.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 (∣gabs∣ ∼ 2.0 × 10−4) in the visible region, suggesting efficient chirality induction to the otherwise achiral BODIPY. The dye's unusually weak fluorescence (Φfl < 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.