N-(2-(N',N'-diethylamino)ethyl)perylene-3,4-dicarboximide and its quaternized derivatives as fluorescence probes of acid, temperature, and solvent polarity.

In this manuscript, we report the fluorescence properties of N-(2-(N',N'-diethylamino)ethyl)perylene-3,4-dicarboximide (1) and its quaternized derivative N-(2-(N',N'- diethyl-N'-methylammonium)ethyl)perylene-3,4-dicarboximide tosylate (2) in organic solvents. The effects of carboxylic acids and amines on the fluorescence properties of these compounds were investigated. In addition, we studied the aggregation and fluorescence properties of (2) and its 9-bromo-substituted derivative (3) in aqueous solution. The fluorescent properties of these compounds change dramatically with the extent of aggregation, thus allowing these compounds to be used as fluorescent probes for changes in temperature and solvent polarity. For instance, the fluorescence emission intensity of 3 increases by about 28 times as the temperature of the solution increases from 10°C to 85°C. The fluorescent intensities of 2 and 3 in methanol are higher than that in water by about 8 and 25 times, respectively.