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Stable Non-fused [22]Pentaphyrins and A Fused [24]Pentaphyrin Displaying Crystal Polymorphism between Hückel and
Tomoki Yoneda1, Tyuji Hoshino1, Saburo Neya1
1Department of Pharmaceutical Sciences, Chiba University, 1-8-1, Inohana, Chuo-ku, Chiba, 260-8675, Japan.
Abstract:
Partially β-substituted and meso-tetrakis(pentafluorophenyl)-substituted [22]pentaphyrins 11 and 12 were synthesized by acid-catalyzed condensation of a meso-C6 F5 -substituted tripyrrane dicarbinol with β-alkylated dipyrromethanes. These [22]pentaphyrins are stable, allowing their characterization by NMR and UV/Vis spectroscopies, and X-ray crystallography, and display strong aromaticity due to 22π-electronic circuits. In methanol, β,β-diethoxycarbonylated pentaphyrin 12 underwent an N-fusion reaction to give N-fused pentaphyrin 13, which exhibits crystal polymorphism between Hückel and Möbius structures, depending upon the recrystallization solvent.
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