{"entity": "publication", "iuid": "5500537f43cc47dfa49d211fd8bed226", "timestamp": "2026-08-10T23:14:24.646Z", "links": {"self": {"href": "https://publications.scilifelab.se/publication/5500537f43cc47dfa49d211fd8bed226.json"}, "display": {"href": "https://publications.scilifelab.se/publication/5500537f43cc47dfa49d211fd8bed226"}}, "title": "Effect of the Aza-N-Bridge and Push-Pull Moieties: A Comparative Study between BODIPYs and Aza-BODIPYs.", "authors": [{"family": "Sch\u00e4fer", "given": "Clara", "initials": "C"}, {"family": "Mony", "given": "J\u00fcrgen", "initials": "J"}, {"family": "Olsson", "given": "Thomas", "initials": "T"}, {"family": "B\u00f6rjesson", "given": "Karl", "initials": "K", "orcid": "0000-0001-8533-201X", "researcher": {"href": "https://publications.scilifelab.se/researcher/cc22ad4eb905493e9ae51616b197edd4.json"}}], "type": "journal article", "published": "2022-03-04", "journal": {"title": "J. Org. Chem.", "issn": "1520-6904", "volume": "87", "issue": "5", "pages": "2569-2579", "issn-l": "0022-3263"}, "abstract": "In the field of fluorescent dyes, difluoroboron-dipyrromethenes (BODIPY) have a highly respected position. To predict their photophysical properties prior to synthesis and therefore to successfully design molecules specifically for one's needs, a solid structure-function understanding based on experimental observations is vital. This work delivers a photophysical evaluation of BODIPY and aza-BODIPY derivatives equipped with different electron-withdrawing/-donating substituents. Using combinatorial chemistry, pyrroles substituted with electron-donating/-withdrawing substituents were condensed together in two different manners, thus providing two sets of molecules. The only difference between the two sets is the bridging unit providing a so far lacking comparison between BODIPYs and aza-BODIPYs structural homologues. Replacing the meso-methine bridge with an aza-N bridge results in a red-shifted transition and considerably different, temperature-activated, excited-state relaxation pathways. The effect of electron-donating units on the absorption but not emission for BODIPYs was suppressed compared to aza-BODIPYs. This result could be evident in a substitution pattern-dependent Stokes shift. The outlook of this study is a deeper understanding of the structure-optics relationship of the (aza)-BODIPY-dye class, leading to an improvement in the de novo design of tailor-made molecules for future applications.", "doi": "10.1021/acs.joc.1c02525", "pmid": "35188769", "labels": {"Swedish NMR Centre": null}, "xrefs": [{"db": "pmc", "key": "PMC8902755"}], "notes": [], "created": "2022-04-25T12:01:39.846Z", "modified": "2025-10-17T13:03:54.931Z"}