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Despite their tetrapyrrole frameworks being small, akin to well\u2010known porphyrins, these species exhibit an unusually narrow HOMO\u2013LUMO gap, resulting in an unprecedentedly low\u2010energy absorption in the second near\u2010infrared (NIR\u2010II) region. Density functional theory (DFT) calculations revealed unique d<jats:sub>\u03c0<\/jats:sub>\u2010p<jats:sub>\u03c0<\/jats:sub>\u2010conjugated electronic structures involving the metal d<jats:sub>\u03c0<\/jats:sub>\u2010ligand p<jats:sub>\u03c0<\/jats:sub> hybridized molecular orbitals of <jats:bold>1M<\/jats:bold>. Magnetic circular dichroism (MCD) spectroscopy confirmed distinct electronic structures. Remarkably, the complexes feature an open\u2010metal coordination site in the peripheral NN dipyrrin site, forming hetero\u2010metal complexes (<jats:bold>1Pd\u2010BF<jats:sub>2<\/jats:sub><\/jats:bold> and <jats:bold>1Pt\u2010BF<jats:sub>2<\/jats:sub><\/jats:bold>) through boron difluoride complexation. The resulting hetero metalla\u2010carbaporphyrinoid species displayed further redshifted NIR\u2010II absorption, highly efficient photothermal conversion efficiencies (<jats:italic>\u03b7<\/jats:italic>; 62\u201365\u2009%), and exceptional photostability. Despite the challenges associated with the theoretical and experimental assessment of d<jats:sub>\u03c0<\/jats:sub>\u2010p<jats:sub>\u03c0<\/jats:sub>\u2010conjugated metalla\u2010aromaticity in relatively larger (more than 18\u03c0 electrons) polycyclic ring systems, these organometallic planar tetrapyrrole systems could serve as potential molecular platforms for aromaticity\u2010relevant NIR\u2010II dyes.<\/jats:p>","DOI":"10.1002\/anie.202405059","type":"journal-article","created":{"date-parts":[[2024,4,2]],"date-time":"2024-04-02T16:06:40Z","timestamp":1712074000000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":22,"title":["Metalla\u2010Carbaporphyrinoids Consisting of an Acyclic N\u2010Confused Tetrapyrrole Analogue Served as Stable Near\u2010Infrared\u2010II 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