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An Improved Protocol for the Synthesis of 2‐Nitro‐7,8,17,18‐tetrabromo‐5,10,15,20‐tetraphenylporphyrin and its Conformational Aspects by Electrochemistry and Spectroscopy
Author(s) -
Prasath R.,
Bhavana P.
Publication year - 2014
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.1867
Subject(s) - chemistry , tetraphenylporphyrin , porphyrin , nitro , derivative (finance) , electrochemistry , redox , stereochemistry , medicinal chemistry , photochemistry , organic chemistry , alkyl , electrode , financial economics , economics
An improved methodology is reported for the synthesis of 2‐nitro‐7,8,17,18‐tetrabromo‐5,10,15,20‐tetraphenylporphyrin by the β‐mononitration of 2,3,12,13‐tetrabromo‐5,10,15,20‐tetraphenylporphyrin using 50% HNO 3 . The copper derivative of this compound showed the expected trend in redox potentials where the free‐base form showed an opposite one on comparing with the corresponding non‐nitro analogs. This opposite trend is ascribed to the role of nitro group in dictating the extent of nonplanarity of the porphyrin as indicated by the electronic and 1 H NMR spectral studies.