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Synthesis of Novel Symmetric Porphyrin Schiff Base Dimers by Solid–Liquid Reaction Methodology
Author(s) -
Yaseen Muhammad,
Farooq Zahid,
Mahmood Mian H. R.,
Ahmad Sheikh Asrar,
Nazir Shahbaz,
Anjum Khalid Mahmood,
Naqvi Syed Ali Raza
Publication year - 2019
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.3526
Subject(s) - chemistry , porphyrin , schiff base , monomer , solvent , condensation reaction , photochemistry , crystallization , condensation , polymer chemistry , organic chemistry , catalysis , polymer , physics , thermodynamics
A new convenient solid–liquid condensation reaction procedure for the synthesis of novel asymmetric and symmetric meso ‐tetraarylporphyrin and metalloporphyrin Schiff bases is reported. The condensation reaction between β‐formyl porphyrin or metalloporphyrins and aromatic amines was carried out at solid–liquid interface by using neutral alumina powder as a solid support for β‐formyl porphyrin or metalloporphyrins and absolute ethanol as the carrier solvent for aromatic amines. Six different asymmetric porphyrin/metalloporphyrin Schiff bases were synthesized via solid–liquid interface reaction methodology. The same solid–liquid synthetic methodology was applied for the synthesis of six novel symmetric Schiff base porphyrin/metalloporphyrin dimers. The comparison of UV–visible spectra of porphyrin Schiff base monomers and dimers revealed that some degree of electronic perturbation has occurred upon dimerization as the Soret bands of the monomers underwent peak broadening along with red shifts. Column chromatography and crystallization were used to purify the compounds. Fourier transform infrared, UV–visible, elemental analysis, 1 H NMR, and mass spectrometry were used to characterize the newly synthesized compounds.