Abstract

Simultaneous synthesis of meso-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 corresponding meso-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 extended [Formula: see text] conjugation.

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