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Synthesis and Spectroscopic Properties of Non‐Symmetrical Benzo‐Annulated Porphyrazines and Their Metal Complexes
Author(s) -
Vagin Sergej I.,
Hanack Michael
Publication year - 2002
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200208)2002:16<2859::aid-ejoc2859>3.0.co;2-e
Subject(s) - chemistry , phthalonitrile , metal , annulation , solubility , spectral line , nonlinear optical , nmr spectra database , proton nmr , condensation , stereochemistry , polymer chemistry , organic chemistry , phthalocyanine , physics , nonlinear system , astronomy , quantum mechanics , catalysis , thermodynamics
New highly stable benzo‐fused m ‐trifluoromethylphenyl porphyrazines and their complexes with Mg and In were synthesized by cross‐condensation of phthalonitrile and bis( m ‐trifluoromethylphenyl)fumaronitrile. Their 1 H and 13 C NMR spectra were recorded and described. The Q‐ and B‐bands in the UV/Vis spectra of the metal complexes show the characteristic splitting upon consecutive benzo‐annulation. The strong variation of spectral features upon benzo‐fusing and metallation/demetallation, as well as the good solubility of the metal complexes in organic solvents, make these materials potentially valuable for optical applications including nonlinear optics. (© Wiley‐VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)