A Modified Vilsmeier–Haack Strategy to Construct β-Pyridine-Fused 5,10,15,20-Tetraarylporphyrins

Pargat Singh; Mahendra Nath

doi:10.1055/s-0040-1707429

CC BY-NC-ND 4.0 · SynOpen 2020; 04(02): 44-50
DOI: 10.1055/s-0040-1707429

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This is an open access article published by Thieme under the terms of the Creative Commons Attribution-NonDerivative-NonCommercial-License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by-nc-nd/4.0/) (2020) The Author(s)

A Modified Vilsmeier–Haack Strategy to Construct β-Pyridine-Fused 5,10,15,20-Tetraarylporphyrins

Pargat Singh

,

Mahendra Nath ∗

Department of Chemistry, Faculty of Science, University of Delhi, Delhi-110 007, India Email: mnath@chemistry.du.ac.in

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Abstract

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Abstract

A modified Vilsmeier–Haack strategy has been developed to construct a novel series of π-extended nickel(II) or copper(II) complexes of 2-chloro-3-formyl- and 3-formylpyrido[2,3-b]porphyrins from 2-acetamido-meso-tetraarylporphyrins. After chromatographic purification and spectral characterization, nickel(II) complexes of 2-chloro-3-formyl- and 3-formylpyrido[2,3-b]porphyrins underwent reaction with malononitrile under Knoevenagel conditions to afford new porphyrins with extended π-conjugation in appreciable yields. On photophysical investigation, the newly prepared pyridoporphyrins displayed a significant redshift in their electronic absorption spectra as compared to simple meso-tetraarylporphyrin precursors.

Key words

2-chloro-3-formylpyrido[2,3-b]porphyrins - 3-formylpyrido[2,3-b]porphyrins - Knoevenagel condensation - redshift - synthesis - Vilsmeier–Haack reaction

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