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Pyridine‐Fused Bis(azacorrole)s: Easily Accessible NIR III Absorbing Cation Radicals and Biradicaloids of Antiaromatic Ground State
Autorzy
Rok wydania
2025
Czasopismo
Numer woluminu
12
Strony
2416223/1-2416223/14
DOI
10.1002/advs.202416223
Kolekcja
Język
Angielski
Typ publikacji
Artykuł
A family of pyridine-fused bis(porphyrinoids) is obtained, includingconstitutionally isomeric bis(azacorrole)s, azacorrole-oxacorrole, as well asazacorrole-norcorrole heterodimers by two distinct synthetic approaches.Spectroscopic characteristics, corroborated by Density Functional Theory(DFT) calculations, indicate aromaticity of the bis(azacorrole) as well asazacorrole-oxacorrole products, while for the azacorrole-norcorroleheterodimers, the presence of both dia- and paratropic currents is detected.Electrochemical analyses indicate facile chemical access to cation radicals anddicationic species that have been characterized by electronic and electron spinresonance spectroscopy as well as by DFT calculations. Monocations give riseto the relatively strong absorption bands in the near infra red (NIR) regionbetween 2400 and 3200 nm, while dications are characterized by a series ofabsorptions between 1000 and 2200 nm. Electron spin resonance (ESR)experiments indicate the presence of singlet-triplet spin equilibria for thedications. For the dication of bis(azacorrole) of the most planar structure, thesinglet ground state is established, and low temperature nuclear magneticresonance (NMR) as well as gauge-independent atomic orbital NMRcalculations indicate its antiaromatic character.
Słowa kluczowe
antiaromaticity, aromaticity, biradicaloids, porphyrinoids, radicals
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Pełny tekst licencji: https://creativecommons.org/licenses/by/3.0/pl/legalcode
Adres publiczny
http://dx.doi.org/10.1002/advs.202416223
Strona internetowa wydawcy
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