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

IŞIK 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
  • Sayfa Sayıları: ss.7188-7191
  • Atatürk Üniversitesi Adresli: Evet

Özet

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 ( divide g(abs) divide similar to 2.0 x 10(-4)) in the visible region, suggesting efficient chirality induction to the otherwise achiral BODIPY. The dye's unusually weak fluorescence (phi(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.