Nitrothienylporphyrins: Synthesis, crystal structure and, the effect of position and number of nitro groups on the spectral and electrochemical properties

This article describes the investigation on the effect of orientation of the meso thienyl groups of porphyrins in deciding the site of nitration. The thienyl rings present at the meso position is found to be more susceptible for electrophilic nitration reaction than the pyrrole β-position in the molecules where there is a better conjugation between the thienyl rings and the porphyrin π-system. Signal corresponding to the imino hydrogens in the proton NMR spectrum of meso nitrothienylporphyrins get shifted to upfield with increase in the number of nitro groups on the porphyrin. This is also due to the extended conjugation of the porphyrins π-system with the meso thienyl rings. The above observations are also supported by the redox potentials of those compounds.

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► Facile synthesis of meso mononitrothienylporphyrin.
► Study on the electronic requirement on nitration of porphyrin.
► Effect of number and position of nitro groups on electronic properties of porphyrins.
► Upfield shift of NMR signals of porphyrin imino hydrogens with number of nitro groups.