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

Date

2022-06-01

Author

Işık, Murat
Dündar, Esra
ŞAHİN, Ertan
Tanyeli, Cihangir

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© 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.

URI

https://www.scopus.com/inward/record.uri?partnerID=HzOxMe3b&scp=85131873963&origin=inward
https://hdl.handle.net/11511/98032

Journal

Chemical Communications

DOI

https://doi.org/10.1039/d2cc02179j

Collections

Department of Chemistry, Article

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Citation Formats

M. Işık, E. Dündar, E. ŞAHİN, and C. Tanyeli, “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, Accessed: 00, 2022. [Online]. Available: https://www.scopus.com/inward/record.uri?partnerID=HzOxMe3b&scp=85131873963&origin=inward.