• Azulicorrole 

      Larsen, Simon; Mccormick-Mcpherson, Laura J; Teat, Simon J.; Ghosh, Abhik (Journal article; Tidsskriftartikkel; Peer reviewed, 2019-04-12)
      Acid-catalyzed condensation of pyrrole, 4-trifluoromethylbenzaldehyde, and azulene, followed by DDQ oxidation, has resulted in the isolation of the novel macrocycle azulicorrole, arguably the first example of a carbacorrole aside from N-confused corrole. Despite poor yields (<1%), the free ligand could be structurally characterized and converted to the formal Cu(III) and Au(III) derivatives, of which ...
    • Isocorroles as Homoaromatic NIR-Absorbing Chromophores: A First Quantum Chemical Study 

      Foroutan-Nejad, Cina; Larsen, Simon; Conradie, Jeanet; Ghosh, Abhik (Journal article; Tidsskriftartikkel; Peer reviewed, 2018-08-10)
      Density functional theory calculations of magnetically induced current densities have revealed high diatropic ring currents in unsubstituted isocorrole consistent with homoaromatic character. An examination of the Kohn-Sham molecular orbitals showed clear evidence of homoconjugative interactions in four occupied π-type molecular orbitals as well as in the LUMO. Remarkably, substituents at the saturated ...
    • New Corrole Analogues: Isocorroles and Azulicorrole 

      Larsen, Simon (Doctoral thesis; Doktorgradsavhandling, 2020-02-25)
      Porphyrinoids are a family of molecules, which consist of large ring structures or macrocycles. One of the oldest, and most important, of the porphyrinoids is the biological molecule called porphyrin. Since the dawn of life, porphyrins have orchestrated photosynthesis and oxygen respiration, two of the most important energy-generating processes in nature. In addition to porphyrins, other porphyrinoids ...
    • A new fluorous-tagged porphyrinoid 

      Larsen, Simon (Master thesis; Mastergradsoppgave, 2012-08-16)
      The field of corrole chemistry has flourished over the past decade. Simple and high-yielding procedures have made the corrole ligand readily available, and several procedures on how to functionalize and otherwise modify corroles and their metal complexes have been reported. During an attempt to synthesize corrole from a fluorous tagged aromatic aldehyde a new porphyrinoid has been isolated from ...
    • Rapid one-pot synthesis of pyrrole-appended isocorroles 

      Larsen, Simon; McCormick, Laura J; Ghosh, Abhik (Journal article; Tidsskriftartikkel; Peer reviewed, 2019-03-06)
      Free-base <i>meso</i>-triarylcorroles have been found to undergo oxidative coupling with an excess of pyrrole in dichloromethane in the presence of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) affording 5/10-pyrrole-appended isocorroles in reasonable yields (35–60%) and in a matter of seconds. The free-base isocorrole ligands could all be complexed to copper with Cu(OAc)<sub>2</sub>·H<sub>2</sub>O ...
    • Transition-Metal Isocorroles as Singlet Oxygen Sensitizers 

      Larsen, Simon; Adewuyi, Joseph A.; Ung, Gaël; Ghosh, Abhik (Journal article; Tidsskriftartikkel; Peer reviewed, 2023-05-04)
      Building on a highly efficient synthesis of pyrrole-appended isocorroles, we have worked out conditions for manganese, palladium, and platinum insertion into free-base 5/10-(2-pyrrolyl)-5,10,15-tris(4-methylphenyl)isocorrole, H<sub>2</sub>[5/10-(2-py)- TpMePiC]. Platinum insertion proved exceedingly challenging but was finally accomplished with cis-Pt(PhCN)<sub>2</sub>Cl<sub>2</sub>. All the ...