Journal
DYES AND PIGMENTS
Volume 133, Issue -, Pages 345-353Publisher
ELSEVIER SCI LTD
DOI: 10.1016/j.dyepig.2016.06.015
Keywords
Diarylmaleimides; Piezochromism; Data recording; pH; Nanoparticles; Explosive
Funding
- National Natural Science Foundation of China [21374017, 21574021]
- Specialized Research Fund for the Doctoral Program of Higher Education [20093223110002, 20123503120002]
- Program for Innovative Research Team in Science and Technology in Fujian Province University (IRTSTFJ)
- Natural Science Foundation of Fujian Province [2013H0018]
- Educational Commission of Fujian Province [JA14068]
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A series of carbazole-based diphenyl maleimide dyes with different N-substituent were synthesized through an Ullmann reaction in high yields. The dyes exhibit an intense emission in the solid state for their twisted conformation fixed by weak intermolecular interactions, resulting in the hindrance of the internal rotations. Their solid-stated emission wavelength and intensity are sensitive to external stimuli (like heat, pressure and vapor), due to a crystal-to-crystal or crystal-to-amorphous phase transition. Based on the multi-stimuli-responsive fluorescence properties of the N-benzyl analogue, two kinds of applications were explored. One is rewritable data recording processes including solvent writing and vapor writing. The other is sensing for low hydrostatic pressure (0-25 MPa). Interestingly, nanoparticles of the dyes formed in aqueous solution could effectively detect explosive and pH changes. A 15 ppm concentration of picric acid quenched the fluorescence of the N-methyl analogue with the detectable limit calculated to be 0.13 ppm. The N-methyl analogue also showed a different emission color and intensity over the pH range 12-14, which originated from the hydrolysis of the dye molecules in the strongly basic solution. (C) 2016 Elsevier Ltd. All rights reserved.
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