Two kinds of 1 H-pyrazoloimidazopyridine (PIP) derivatives consisting of 5-5-6 ring condensed heteroaromatic systems, that is, 1 H-pyrazolo [5', 1': 2, 3] imidazo [4, 5-b] pyridine (PIP-A) and 1 Hpyrazolo [1', 5': 1, 2] imidazo [4, 5-c] pyridine (PIP-B), are very interesting skeletons from theviewpoint of dye formation, because they possess an active methylene at 3-position in their ring systems. These two PIP derivatives were synthesized and their coupling reactivity with quinonediimine (QDI) was investigated. It was revealed that they were able to couple with QDI to form azomethine cyan dyes (PIP-A-Dye and PIP-B-Dye respectively).
We measured absorption spectra and reduction potentials of these dyes and it was found that, (i) the spectral absorption characteristics and the reduction potential of PIP-A-Dye were very similar to those of PIP-B-Dye, (ii) both these dyes were hypsochromically shifted in hue, compared with the dye of conventional phenolic cyan coupler (PHE-Dye), (iii) both these dyes had more desirable spectral absorption characteristics than PHE-Dye, (iv) both these dyes had more negative reduction potentials than PHEDye, which would be favorable for prevention of heat-induced cyandye fading.
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