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Click Synthesis, Aggregation-Induced Emission, E/Z Isomerization, Self-Organization, and Multiple Chromisms of Pure Stereoisomers of a Tetraphenylethene-Cored Luminogen
Abstract
It has been difficult to decipher the mechanistic issue whether E/Z isomerization is involved in the aggregation-induced emission (AIE) process of a tetraphenylethene (TPE) derivative, due to the difficulty in the synthesis of its pure E and Z conformers. In this work, pure stereoisomers of a TPE derivative named 1,2-bis{4-[1-(6-phenoxyhexyl)-4-(1,2,3-triazol)yl]phenyl}-1,2-diphenylethene (BPHTATPE) are successfully synthesized. Both isomers show remarkable AIE effect (α(AIE) ≥ 322) and high fluorescence quantum yield in the solid state (Φ(F) 100%). The conformers readily undergo E/Z isomerization upon exposure to a powerful UV light and treatment at a high temperature (>200 °C). Such conformational change, however, is not observed under normal fluorescence spectrum measurement conditions, excluding the involvement of the E/Z isomerization in the AIE process of the TPE-based luminogen. The molecules of (E)-BPHTATPE self-organize into ordered one-dimensional nanostructures such as microfibers and nanorods that show obvious optical waveguide effect. BPHTATPE shows rich chromic effects, including mechano-, piezo-, thermo-, vapo-, and chronochromisms. Its emission peak is bathochromically shifted by simple grinding and pressurization and the spectral change is reversed by fuming with a polar solvent, heating at a high temperature, or storing at room temperature for some time. The multiple chromic processes are all associated with changes in the modes of molecular packing.
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Metadata
- Authors
- Wang, J., Mei, J., Hu, R., Sun, J. Z., Qin, A., & Tang, B. Z.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2012-06-06
- Volume
- 134
- Issue
- 24
- Pages
- 9956-9966
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W1963505485
- Cited by
- 593
- References
- 90
- FWCI
- 25.92
- Type
- journal article
- Language
- en
- Open access
- closed
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