Synthesis and properties of tetra-aryl azobispyrroles
The chemistry of the azobispyrrole framework, which melds the impressive electronic capabilities of the azo (-NN-) moiety and the pyrrole heterocycle, is significantly under-developed. Herein, the synthesis and characterisation of a series of azobispyrroles substituted with four aryl groups are presented. The steric bulk of aryl groups at the β-positions of the pyrrolic building blocks controls the degree to which azobispyrrole formation competes with aza-dipyrrin formation when using nitrobutanones as starting materials. The ability of aryl groups at the α-positions of the pyrrolic building blocks to influence conformational stability is discussed, as is the consequent control of photophysical properties.
Authors
- Alison Thompson (ORCID: https://orcid.org/0000-0003-4231-3446)
- Steve Sequeira
- Adil Alkaş (ORCID: https://orcid.org/0000-0002-9375-7963)
- Roberto M. Diaz‐Rodriguez (ORCID: https://orcid.org/0000-0002-4778-0687)
- Rosinah Liandrah Gapare (ORCID: https://orcid.org/0000-0003-1836-6118)
- Katherine N. Robertson (ORCID: https://orcid.org/0000-0002-5602-8059)
- James W. Hilborn
- Em C. Sullivan
- Emily B. Brown
- Mmasinachi Atansi
- Madeleine Dearden
Institutions
- Dalhousie University (CA)
- Saint Mary's University (CA)
Publication Details
- Journal
- Organic & Biomolecular Chemistry
- Published
- 2025-01-01
- DOI
- https://doi.org/10.1039/d5ob01104c
- Primary Topic
- Porphyrin and Phthalocyanine Chemistry
- Type
- article
- Field-Weighted Citation Impact
- 0.00
Funders
- Canada Research Chairs
- Dalhousie University
- Research Nova Scotia
- Natural Sciences and Engineering Research Council of Canada