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, cilt.58, sa.51, ss.7188-7191, 2022 (SCI-Expanded) identifier identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 58 Sayı: 51
  • Basım Tarihi: 2022
  • Doi Numarası: 10.1039/d2cc02179j
  • Dergi Adı: Chemical Communications
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Chemical Abstracts Core, Chimica, Communication Abstracts, Compendex, EMBASE, MEDLINE, DIALNET, Index Chemicus (IC)
  • Sayfa Sayıları: ss.7188-7191
  • Orta Doğu Teknik Üniversitesi Adresli: Evet

Özet

© 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.