H. Icil et al., Synthesis and spectroscopic characterization of water soluble perylene tetracarboxylic diimide derivatives, SPECT LETT, 34(5), 2001, pp. 605-614
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.