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Updated: Oct 25, 2026

Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach
Published on: June 10, 2021
Dipyrrin-Strapped NiII Porphyrins
Boyu Xiao1, Le Liu1, Yutao Rao1
1Key Laboratory of the Assembly and Application of Organic Functional Molecules of Hunan Province, College of Chemistry and Chemical Engineering, Hunan Normal University, Changsha410081, China.
Abstract:
A dipyrrin-strapped NiII porphyrin and its anthracene-bridged dimer were synthesized as the first examples of free base carbasubporphyrins-fused porphyrins by Suzuki-Miyaura coupling reaction of 2,18-bis(5-borylpyrr-2-yl)-substituted NiII porphyrin with 9,10-bis(2,2'-dibromoethenyl)anthracene. Upon treatment with BPhCl2 and triethylamine (TEA), these porphyrins were converted into the corresponding BIII carbasubporphyrin complexes. A similar coupling reaction of the diborylated NiII porphyrin with 9-(2,2'-dibromoethenyl)fluorene gave a meso-fluorenyl adduct, which was also converted into a similar BIII complex. These BIII complexes have a dual electronic system consisting of aromatic 18π-porphyrin and a global antiaromatic 24π circuit.
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