Synthesis of Soluble Perylenebisamidine Derivatives. Novel Long-Wavelength Absorbing and Fluorescent Dyes

Abstract

Extension of the π-system of 1,6,7,12-tetrakis(aryloxy)-3,4,9,10-perylenetetracarboxdiimide was achieved by the condensation of 1,6,7,12-tetrakis(aryloxy)-3,4,9,10-perylenetetracarboxylic bisanhydride with 1,2-diaminobenzene, 1,8-diaminonaphthalene, and 9,10-diaminophenanthrene. A full characterization of the resulting novel long-wavelength absorbing dyes by field-desorption mass spectrometry, UV−vis, IR, and 1H and 13C NMR spectroscopies is given. Photostability and thermal stability are reported and discussed.