Synthesis and spectroscopic characterization of water soluble perylene tetracarboxylic diimide derivatives

Abstract

Two new perylene dye, N,N'bis(4-hydroxyphenyl)-3,4,9,10 perylenebis (dicarboximide) (1) and N,N'-bis-(3,3,5,5-tetramethyl piperidine)-3,4,9,10-perylenebis (dicarboximide) (2) have been synthesized. They are both soluble in water. A limited number of water soluble perylene dyes published in literature have been obtained in pure grade only with column chromatography. For this 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) were measured as 4.4 x 10(-5) g/ml and 5.1 x 10(-3) g/ml respectively in distilled water at pH: 7. The solubility of N.N'-bis-(3,3,5,5-tctramethyl piperidine)-3,4,9,10-perylenebis (dicarboximide) was increased with decreasing pH. The chemical and photochemical stabilities of 1, and 2 are very high. The 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.