Synthesis and structural diversification of circularly polarised luminescence active, helically chiral, "confused" N,N,O,C‐BODIPYs**

Rebecca G. Clarke, Jake Weatherston, Rafid A. Taj-Aldeen, Paul G. Waddell, William McFarlane, Thomas J. Penfold, Jonathan Bogaerts, Lewis E. MacKenzie, Wouter Herrebout, Robert Pal, Michael J. Hall

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Abstract

Helically chiral boron-chelated dipyrromethene (BODIPY) dyes are known to exhibit solution phase circularly polarized luminescence (CPL), but examples are limited to a few synthetically accessible molecular architectures. We report a B−N chelation, SNAr, Suzuki cross-coupling, B−O chelation cascade reaction for the synthesis of understudied helically chiral, N,N,O,C-boron chelated, "confused" BODIPYs, from readily accessible 3,5-dibromo-BODIPY starting materials. Using this approach we have prepared a series of helically chiral "confused" BODIPYs with variation of the 3,5-subsitutents. Following resolution by chiral HPLC, absolute stereochemistry was assigned through comparison of the experimental and calculated ECD spectra, and solution phase chiroptical properties including CPL were determined (|glum| from 2.1 to 3.7×10−3; BCPL from 11.3 to 27.2).
Original languageEnglish
Article numbere202200194
Number of pages6
JournalChemPhotoChem
Early online date19 Sept 2022
DOIs
Publication statusPublished - 18 Oct 2022

Keywords

  • BODIPYs
  • cascade reactions
  • circularly poised luminescence
  • electronic circular dichroism spectroscopy
  • helically chiral compounds

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