Pyrrolizine-3-ones: Synthesis and evaluation of photophysical properties


Isik Tasgin D., Bayraktar I.

Synthetic Communications, vol.54, no.3, pp.216-228, 2024 (SCI-Expanded, Scopus) identifier identifier

  • Publication Type: Article / Article
  • Volume: 54 Issue: 3
  • Publication Date: 2024
  • Doi Number: 10.1080/00397911.2023.2292699
  • Journal Name: Synthetic Communications
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Chemical Abstracts Core, Chimica
  • Page Numbers: pp.216-228
  • Keywords: fluorescence, large stokes shift, photophysical properties, pyrrolizinones, small-molecule organic dyes
  • Hacettepe University Affiliated: Yes

Abstract

We describe a synthetic approach for pyrrolizine-3-one derivatives and their photophysical properties. These compounds are prepared by a series of reactions employing the substituted pyrroles in one-pot, two-step oxidation, and intramolecular cyclization processes. The photophysical properties of the synthesized compounds were studied by using UV–Vis and fluorescence spectroscopy in different solvents. Maximum absorbance peaks were observed around 306–416 nm and maximum fluorescence emission around 603–614 nm and 465–498 nm for pyrrolyl and N-methyl pyrrolyl substituents, respectively. The introduction of a pyrrolyl substituent had a significant impact on the Stokes shifts (192–206 nm) and quantum yield values ranged from 0.002 to 0.046.