Abstract
Aggregation-induced emission (AIE) has become a hot research area and tremendous amounts of AIE-active luminogens (AIEgens) have been generated. To further promote the development of AIE, new AIEgens are highly desirable. Herein, new AIEgens based on tetraphenylpyrimidine (TPPM) are rationally designed according to the AIE mechanism of restriction of intramolecular motion, and facilely prepared under mild reaction conditions. The photophysical property of the generated TPPM, TPPM-4M and TPPM-4P are systematically investigated and the results show that they feature the aggregation-enhanced emission (AEE) characteristics. Theoretical study shows the high-frequency bending vibrations in the central pyrimidine ring of TPPM derivatives dominate the nonradiative decay channels. Thanks to the AEE feature, their aggregates can be used to detect explosives with super-amplification quenching effects, and the sensing ability is higher than typical AIE-active tetraphenylethene. It is anticipated that TPPM derivatives could serve as a new type of widely used AIEgen based on their facile preparation and good thermo-, photo- and chemostabilities.
Highlights
The research on aggregation-induced emission (AIE) is drawing increasing interest since it can solve the aggregation-caused quenching (ACQ) problem encountered by traditional organic luminophores
Tetraphenylpyrazine (TPP)-based active luminogens (AIEgens) were designed based on the restriction of the intramolecular rotation mechanism and facilely synthesized
A new type of AIEgen based on tetraphenylpyrimidine (TPPM) was rationally designed and facilely prepared
Summary
The research on aggregation-induced emission (AIE) is drawing increasing interest since it can solve the aggregation-caused quenching (ACQ) problem encountered by traditional organic luminophores. AIE-active luminogens (AIEgens) possess relatively high emission efficiency in the aggregate or solid states, which meets the requirements for practical applications in organic light-emitting diodes, optical waveguides, biosensors and bioimaging, etc. AIEgens exhibit remarkable advantages over traditional ACQ luminophores in aggregate and solid states, so constructing new AIEgens is of great importance for promoting the development of AIE research. The introduction of aromatic nitrogen heterocycles could help produce electron donor-acceptor structures to fine-tune the light emission in a wide range. Along these lines, tetraphenylpyrazine (TPP)-based AIEgens were designed based on the restriction of the intramolecular rotation mechanism and facilely synthesized
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