Highly selective discriminating E, E/E, Z isomers of functionalized 1-phenyl-2,5-divinyl-1H-pyrrole for n-/sec-/tert-butyl amines and as temperature sensor

A series of novel E, E/E, Z isomers based on 5-(2-cyano-3-ethoxy-3-oxoprop-1-en-1-yl)-1H-pyrrol-2-yl acrylic acid have been successfully synthesized. The comparative studies between compounds presenting E, E/E, Z isomers on the properties of emission and effects of temperature had been discussed. Interestingly, the E, Z, and E, E isomers emitted different luminous colors and aggregation-induced emission (AIE) properties. Notably, the E, Z-OC2H5COOH and E, E-OC2H5COOH loaded on filter paper could identify alkaline compounds. Furthermore, E, E-OC2H5COOH strips could selectively discriminate for n-/sec-/tert-butylamine by changing the color of the fluorescence. In addition, E, E-OC2H5COOH, doped into polymer dimethyl silicone (PDMS) film could exhibit an evident change in emission color from orange to yellow at 90 °C and gradually vanished at 190 °C, while that of E, Z-OC2H5COOH didn't change significantly with heating. Therefore, the configuration of two double bonds can be used to regulate the change of fluorescence, improve the chemical and physical properties of materials, and break through the deficiency of single configuration regulation. A series of novel multipurpose AIE/MFC/Sensor E, E/E, Z luminogens have been concisely synthesized. Compared with E, Z isomer, the E, E-OC2H5COOH showed the significant MFC behavior. Notably, E, E-OC2H5COOH-load test strips firstly displayed efficient discriminate character for n-/sec-/tert-butylamine with conspicuous emission color switching from orange to slight blue, dark blue and yellow. Interestingly, E, E-OC2H5COOH doped PDMS films behave as luminescent temperature sensor at around 90 °C and 170 °C. This work presents a new strategy to achieve multipurpose AIE-active luminogens with facile configuration control. [Display omitted] •A series of novel multipurpose AIE/MFC/Sensor E, E/E, Z luminogens were synthesized.•Compared with E, Z isomer, the E, E-OC2H5COOH showed the significant MFC behavior.•Notably, E, E-OC2H5COOH-load test strips firstly displayed efficient discriminate character for n-/sec-/tert-butylamine.•Interestingly, E, E-OC2H5COOH doped PDMS films behave as luminescent temperature sensor at around 90 °C and 170 °C.•A new strategy was developed to achieve multipurpose AIE-active luminogens with facile configuration control.