Pyrrolylquinoline-BF2 and BPh2 BODIPY-type analogues: Synthesis, structural analysis and photophysical properties

Abdulrahman A. Alsimaree (Lead / Corresponding author), Omar M. Alatawi, Paul G. Waddell, David P. Day, Nawaf I. Alsenani, Julian G. Knight

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Abstract

Two new pyrrolylquinoline-substituted heteroaromatic-containing compounds bearing a central boron bridge have been prepared by a short, high-yielding sequence consisting of Suzuki-coupling of 8-bromoquinoline and N-Boc 2-pyrroleboronic acid, thermolytic tert-butyloxycarbonyl deprotection, and subsequent boron chelation (either using boron trifluoride or triphenylborane). Both derivatives display longer wavelength absorption maxima (λabs max) than a previously reported indolopyridine-BPh2 analogue, in agreement with the smaller HOMO-LUMO energy gap predicted by DFT quantum chemical calculations. Both of the pyrrolylquinoline-boron chelates display weak emission (quantum yields 0.3–0.9%) and the BPh2 complex displays a very broad, long-wavelength emission (λem max = 715 nm, MeCN), which may be due to dimer emission and results in a large pseudo-Stokes’ shift (7753 cm−1) for this compound.

Original languageEnglish
Article number1103
Number of pages11
JournalCrystals
Volume11
Issue number9
DOIs
Publication statusPublished - Sep 2021

Keywords

  • Boron bridged complex
  • DFT analysis
  • Fluorescent molecules
  • Structural analysis
  • X-ray crystal analysis

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