2019/12/27 by K. Yamashita, Kana Nakajima, Yusuke Honda +1 · 1 voice · 1 citation
Chemistry · Materials Science · #Porphyrin and Phthalocyanine Chemistry #Supramolecular Chemistry and Complexes #Synthesis and Properties of Aromatic Compounds
paper · doi:10.1002/chem.201905823
openalex publication_date 2019/12/27 · openalex created_date 2025/10/10 · openalex updated_date 2026/07/09
Abstract Facile redox‐induced aromatic–antiaromatic interconversions were accomplished by using β‐tetracyano‐21,23‐dithiaporphyrin (CN 4 S 2 Por). Introduced cyano groups not only increased the reduction potential of the porphyrin core but also stabilized the antiaromatic isophlorin (CN 4 S 2 Iph) by π conjugation. The reduction of CN 4 S 2 Por with hydrazine in polar solvents quantitatively affords CN 4 S 2 Iph, even under ambient conditions. CN 4 S 2 Iph retains a nearly planar conformation and exhibits considerable antiaromaticity. Aerobic oxidation of CN 4 S 2 Iph to CN 4 S 2 Por occurs in nonpolar solvents. This study was conducted to contribute to the understanding of the structure–antiaromaticity relationship.