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Here we report the preparation of a series of unprecedented stable neutral nickel(II) and copper(II) complexes of \u201cManitoba dipyrromethenes\u201d (MB\u2010DIPYs) in which the organic chromophore is present in the radical\u2010anion state. The new stable radicals have an intense absorption at <jats:italic>\u03bb<\/jats:italic><jats:sub>max<\/jats:sub>\u223c1300\u2005nm and can be either oxidized to regular [M<jats:sup>II<\/jats:sup>(MB\u2010DIPY)]<jats:sup>+<\/jats:sup> (M=Cu or Ni) or reduced to [M<jats:sup>II<\/jats:sup>(MB\u2010DIPY)]<jats:sup>\u2212<\/jats:sup> compounds. The radical nature of the stable [M<jats:sup>II<\/jats:sup>(MB\u2010DIPY)] complexes was confirmed by EPR spectroscopy with additional insight into their electronic structure obtained by UV\u2010Vis spectroscopy, electro\u2010 and spectroelectrochemistry, magnetic measurements, and X\u2010ray crystallography. The electronic structures and spectroscopic properties of the radical\u2010based chromophores were also probed by density functional theory (DFT) and time\u2010dependent DFT (TDDFT) calculations. These nickel(II) and copper(II) complexes represent the first stable radical compounds with a MB\u2010DIPY ligand.<\/jats:p>","DOI":"10.1002\/chem.202201181","type":"journal-article","created":{"date-parts":[[2022,6,8]],"date-time":"2022-06-08T08:52:51Z","timestamp":1654678371000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":7,"title":["Radical Complexes of Nickel(II)\/Copper(II) and Redox Non\u2010innocent MB\u2010DIPY Ligands: Unusual Stability and Strong Near\u2010Infrared Absorption at <i>\u03bb<\/i><sub>max<\/sub> \u223c1300\u2005nm"],"prefix":"10.1002","volume":"28","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-9770-7007","authenticated-orcid":false,"given":"Yuriy V.","family":"Zatsikha","sequence":"first","affiliation":[{"name":"Department of Chemistry University of Manitoba  Winnipeg MB R3T 2\u2005N2 Canada"},{"name":"Enamine Ltd.  Chervonotkatska Street 78 Kyiv 02094 Ukraine"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Liliya I.","family":"Shamova","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of Manitoba  Winnipeg MB R3T 2\u2005N2 Canada"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Michael","family":"Shepit","sequence":"additional","affiliation":[{"name":"Department of Physics and Astronomy University of Manitoba  Winnipeg MB R3T 2\u2005N2 Canada"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Steven M.","family":"Berry","sequence":"additional","affiliation":[{"name":"Department of Chemistry and Biochemistry University of Minnesota\u2013Duluth  Duluth MN 55812 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Fabrice","family":"Thomas","sequence":"additional","affiliation":[{"name":"Univ. 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