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

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.

Graphical Abstract

Keywords:

• pyrrolizinones
• photophysical properties
• small-molecule organic dyes
• large stokes shift
• fluorescence

Disclosure statement

The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.

Acknowledgments

The authors are indebted to Prof. Dr. Canan Ünaleroğlu and Hacettepe University for supplying the laboratory facilities.

Supporting information

Full experimental detail, ¹H and ¹³C NMR spectra, HRMS spectra. This material can be found via the “Supplementary Content” section of this article’s webpage.