Synthesis of nonplanar meso-trifluoromethyl-substituted tetrabenzoporphyrins via oxidation of tetrabutanoporphyrins
Synthesis of nonplanar meso-trifluoromethyl-substituted tetrabenzoporphyrins via oxidation of tetrabutanoporphyrins
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四丁卟啉氧化合成非平面内消旋三氟甲基取代的四苯并卟啉
DOI：
10.1142/s1088424619500664
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发表时间：
2020
期刊：
影响因子：
--
通讯作者：
M. Suzuki
中科院分区：
文献类型：
--
作者：
K. Okinaga;M. Suzuki
同时合成了在5-、5-、10-和5- 15位上具有一个或两个三氟甲基的中-三氟甲基取代四丁基卟啉。产物经2,3-二氯-5,6-二氰-1,4-苯醌回流氧化，可转化为相应的中-三氟甲基取代四苯并卟啉。它们的晶体结构显示由外周取代基的空间排斥引起的非平面畸变，这可以提高四苯并卟啉框架在普通溶剂中的溶解度，而不会失去扩展共轭。
Simultaneous synthesis ofmeso-trifluoromethyl-substituted tetrabutanoporphyrins having one or two trifluoromethyl groups at their 5-, 5,10-, and 5,15-positions has been achieved. The products can be converted into the correspondingmeso-trifluoromethyl-substituted tetrabenzoporphyrins by oxidative treatment with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone under reflux. Their crystal structures reveal nonplanar distortion arising from the steric repulsion of the peripheral substituents, which can enhance the solubility of the tetrabenzoporphyrin framework in common solvents without loss of the extendedconjugation.