Synthesis of meso-fluorotetrabenzoporphyrins

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• 作者：Satoshi Ito ; Noriaki Terada ; Komei Seino ; Daishi Makihata ; Akira Sasaki ; Toru Oba
• 关键词：Porphyrin ; Fluorination ; Retro Diels&ndash ; Alder reaction
• 刊名：Tetrahedron Letters
• 出版年：2013
• 出版时间：30 October, 2013
• 年：2013
• 卷：54
• 期：44
• 页码：5916-5919
• 全文大小：820 K

文摘

Fluorination of quadruply bicyclo[2.2.2]octadiene-fused porphyrin (CP) with 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (Selectfluor) occurred at the meso positions to give a mixture of various meso-fluorinated CPs, which were separated and then quantitatively transformed to the corresponding meso-fluorinated tetrafluorobenzoporphyrins (BPs) at 240 ¡ãC for 30 min. X-ray analysis of the mono-fluoro BPs revealed that the BP skeleton remained flat, which is crucial for retaining aggregation behavior similar to that of the parent BP, thus producing highly crystalline BP derivatives.