Syntheses and Characteristics of Near Infrared Absorbing Metal Complex Dyes with Quinoid Liqands

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The first absorption band of some quinoid derivatives was found to be drastically shifted to longer wavelength with a large increase in the absorption absorption intensity by metal chelate complexation. Utilizing these properties, we designed some new near infrared absorbing metal complex dyes with quinoid ligands. The results are summarized as follows :1. The reaction of sodium 1, 2-naphthoquinone-4-sulfonate with various arylamines and 1, 1-bis[p- (dimethylamino) phenyl]ethylene were efficiently promoted by Ni (II) ion to give 4-aminated, 4-arylated, and 4-vinylated 1, 2-naphthoquinones in good yields. The products with strongly electrondonating 4-substituents were found to be suitable ligands for the synthesis of near infrared absorbing dyes.2. The Diels-Alder reacton of 5, 8-quinolinedione with p- (dimethylamino) -styrenes gave new two kinds of isomeric dyes which showed quite different metallochromic behaviors. Upon addition of metal salts, one of the two isomers showed drastic spectra changes to have an intense absorption band in near infrared region. The color-structure relations were investigated.