Abstract
Materials that have higher fluorescence emission in the solid state than molecules in solution have recently been paid more attention by the scientific community due to their potential applications in various fields. In this work, we newly synthesized benzoxazolyl-imidazole and benzothiazolyl-imidazole conjugates, which show aggregation-induced emission (AIE) features in their solid and aggregate states. It was found that oxygen and sulfur substitutions can dramatically influence the molecular structures and polarities of the dyes, leading to different degrees of the AIE phenomenon. The benzothiazolyl-imidazole molecule has lower polarity compared to that of benzoxazolyl-imidazole; therefore, the dye bearing a benzothiazolyl group shows higher emission intensity and dual emission in aqueous solution. Theoretical calculation results suggest that the benzothiazolyl-imidazole molecules might have electrostatic interactions between sulfur and nitrogen atoms, explaining the experimental observations of lower critical aggregation concentration and photophysical properties both in solution and in the solid state. The theoretical calculations agree with the experimental data, thus demonstrating a potent strategy to gain a deep understanding of the structure–property relationships to design solid-state fluorescent materials.
Highlights
IntroductionMaterials that have higher uorescence emission in the solid and aggregate state than that of molecules in solution have recently been paid more attention by the scienti c community due to their potential applications in various elds, including explosive detection, optoelectronics, photonics, sensing, biomedical applications and so on.[1,2,3,4,5,6,7,8,9,10,11] The concept of aggregation-induced emission (AIE) was discovered in 2001 and since numerous AIEgens have been developed by researchers, academics and others.[12] Until now, several interesting types of AIEgen based on tetraphenylethene,[13,14,15] hexaphenylsilole,[16,17] tetraphenylpyrazine,[18,19] distyrylanthracene,[20,21] boron diiminates[22] and imidazole[23] have been explored
Theoretical calculation results suggest that the benzothiazolyl-imidazole molecules might have electrostatic interactions between sulfur and nitrogen atoms, explaining the experimental observations of lower critical aggregation concentration and photophysical properties both in solution and in the solid state
The theoretical calculations agree with the experimental data, demonstrating a potent strategy to gain a deep understanding of the structure–property relationships to design solid-state fluorescent materials
Summary
Materials that have higher uorescence emission in the solid and aggregate state than that of molecules in solution have recently been paid more attention by the scienti c community due to their potential applications in various elds, including explosive detection, optoelectronics, photonics, sensing, biomedical applications and so on.[1,2,3,4,5,6,7,8,9,10,11] The concept of aggregation-induced emission (AIE) was discovered in 2001 and since numerous AIEgens have been developed by researchers, academics and others.[12] Until now, several interesting types of AIEgen based on tetraphenylethene,[13,14,15] hexaphenylsilole,[16,17] tetraphenylpyrazine,[18,19] distyrylanthracene,[20,21] boron diiminates[22] and imidazole[23] have been explored. The scienti c interest in cyanine dyes is mainly related to their excellent spectral properties, for instance good uorescence
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