A boron dipyrromethene chiral at boron and carbon with a bent geometry: synthesis, resolution and chiroptical properties
Chemical Communications, vol.58, no.51, pp.7188-7191, 2022 (SCI-Expanded, Scopus)
- 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 (SCI-EXPANDED), Scopus, Academic Search Premier, Chemical Abstracts Core, Chimica, Communication Abstracts, Compendex, EMBASE, MEDLINE, DIALNET, Index Chemicus (IC)
- Page Numbers: pp.7188-7191
- Middle East Technical University Affiliated: Yes
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.