Synthesis and spectroscopic characterization of water soluble perylene tetracarboxylic diimide derivatives

Two new perylene dye, N,N'bis(4-hydroxyphenyl)-3,4,9,10 perylenebis (dicarb oximide) (1) and N,N'-bis-(3,3,5,5-tetramethyl piperidine)-3,4,9,10-perylen ebis (dicarboximide) (2) have been synthesized. They are both soluble in wa ter. A limited number of water soluble perylene dyes published in literatur e have been obtained in pure grade only with column chromatography. For thi s reason they are not useful for certain applications. The N,N-bis-(3,3,5,5 -tetramethyl piperidine)-3,4,9,10-perylenebis (dicarboximide) derivative is obtained in high purity with high yield. Solubility of dyes, (1) and (2) w ere measured as 4.4 x 10(-5) g/ml and 5.1 x 10(-3) g/ml respectively in dis tilled water at pH: 7. The solubility of N.N'-bis-(3,3,5,5-tctramethyl pipe ridine)-3,4,9,10-perylenebis (dicarboximide) was increased with decreasing pH. The chemical and photochemical stabilities of 1, and 2 are very high. T he fluorescence quantum yields of compounds are different (0.053 (1), 0.110 (2)). The report includes the electronic absorption and emission spectra, extinction coefficients and fluorescence quantum yields.