Facile Synthesis of Large meso‐Pentafluorophenyl‐Substituted Expanded Porphyrins
Facile Synthesis of Large meso‐Pentafluorophenyl‐Substituted Expanded Porphyrins
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DOI：
10.1002/ejoc.200701132
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发表时间：
2008-03
影响因子：
2.8
通讯作者：
Y. Tanaka;Ji-Young Shin;A. Osuka
中科院分区：
文献类型：
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作者：
Y. Tanaka;Ji-Young Shin;A. Osuka
在酸催化下，中位五氟苯基二吡咯甲烷1(10 0 MM)和五氟苯甲醛2(10 0 MM)在0℃下缩合，得到一系列偶数个吡咯亚基数目高达octadecaphyrin(1.1.1.1.1.1.1.1.1.1.1.1.1.1.1.1.1.1)18的扩展卟啉，产率提高，特别是对于较大的扩展卟啉。X-射线衍射仪分析表明，去氢呋喃(1.1.1.1.1.1.1.1.1.1)10的固相结构为月牙状。随着环尺寸的增加，类SORET吸收带越来越多地红移，但对于hexadecaphyrin(1.1.1.1.1.1.1.1.1.1.1.1.1.1.1.1)16和18，这样的趋势变得接近饱和，它们分别在939和953 nm的近红外区域显示出吸收带。
Acid-catalyzed condensation of meso-pentafluorophenyl dipyrromethane 1 (100 mM) and pentafluorobenzaldehyde 2 (100 mM) 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)