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

Autor: Işık M; Department of Food Engineering, Bingöl University, Bingöl, 12000, Turkey. misik@bingol.edu.tr., Dündar E; Department of Chemistry, Middle East Technical University, 06800 Ankara, Turkey. tanyeli@metu.edu.tr., Şahin E; Department of Chemistry, Atatürk University, Erzurum, 25240, Turkey., Tanyeli C; Department of Chemistry, Middle East Technical University, 06800 Ankara, Turkey. tanyeli@metu.edu.tr.
Jazyk: angličtina
Zdroj: Chemical communications (Cambridge, England) [Chem Commun (Camb)] 2022 Jun 23; Vol. 58 (51), pp. 7188-7191. Date of Electronic Publication: 2022 Jun 23.
DOI: 10.1039/d2cc02179j
Abstrakt: 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.
Databáze: MEDLINE
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