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Facile Synthesis of Large meso ‐Pentafluorophenyl‐Substituted Expanded Porphyrins
Author(s) -
Tanaka Yasuo,
Shin JiYoung,
Osuka Atsuhiro
Publication year - 2008
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200701132
Subject(s) - chemistry , ring (chemistry) , condensation , solid state , absorption (acoustics) , crystallography , stereochemistry , medicinal chemistry , organic chemistry , physics , acoustics , thermodynamics
Acid‐catalyzed condensation of meso ‐pentafluorophenyl dipyrromethane 1 (100 m M ) and pentafluorobenzaldehyde 2 (100 m M ) at 0 °C gave a series of expanded porphyrins with even number of pyrrolic subunits up to octadecaphyrin(1.1.1.1.1.1.1.1.1.1.1.1.1.1.1.1.1.1) 18 in improved yields, particularly for larger expanded porphyrins. The solid‐state structure of decaphyrin(1.1.1.1.1.1.1.1.1.1) 10 was revealed by X‐ray diffraction analysis to be a crescent‐like conformation. The Soret‐like absorption bands are increasinglyredshifted as the size of the ring increases, but such atrend becomes nearly saturated for hexadecaphyrin(1.1.1.1.1.1.1.1.1.1.1.1.1.1.1.1) 16 and 18 , which exhibit bands in the near‐infrared region at 939 and 953 nm, respectively.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)