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The synthesis of an NHC-containing porphyrinoid ligand is presented. The formally antiaromatic 20 πe- macrocyclic framework can be obtained via a 1,3-dipolar cycloaddition ("click-reaction" to form two triazole moieties which were alkylated to the respective triazolium macrocycle. Deprotonation of the ligand precursor with lithium bases to the respective dilithio carbenaporphyrin complex and transmetallation to scandium lead to complexes that exhibit orange fluorescence. Optical property combined with TD-DFT studies verify an aromatic