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Aggregation-Induced Emission Enhancement of 2-(2‘-Hydroxyphenyl)benzothiazole-Based Excited-State Intramolecular Proton-Transfer Compounds
Abstract
A novel class of 2-(2'-hydroxyphenyl)benzothiazole-based (HBT-based) excited-state intramolecular proton-transfer (ESIPT) compounds, N,N'-di[3-Hydroxy-4-(2'-benzothiazole)phenyl]isophthalic amide (DHIA) and N,N'-di[3-Hydroxy-4-(2'-benzothiazole)phenyl]5-tert-butyl-isophthalic amide (DHBIA) has been feasibly synthesized and the properties of their nanoparticles in THF/H2O mixed solvent were investigated. Both compounds were found to exhibit aggregation-induced emission enhancement (AIEE) due to restricted intramolecular motion and easier intramolecular proton transfer in solid state. On identical experimental conditions, the emission of DHBIA aggregates increased more remarkably than that of DHIA. Different aggregation forms of these two organic compounds, due to the steric hindrance of a single tert-butyl group, could be responsible for the notably different degrees of the fluorescence enhancement. Their aggregation modes were investigated on the basis of time-dependent absorption, scanning electron microscope (SEM) images, and molecular modeling with theoretical calculation. The photophysical dynamics were also depicted based on the extremely fast ESIPT four-level cycle.
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Cites
Aggregation-induced emission of 1-methyl-1,2,3,4,5-pentaphenylsilole
Luo, J., Xie, Z., Lam, J. W. Y., Cheng, L., Tang, B. Z., Chen, H., Qiu, C., Kwok, H. S., Zhan, X., Liu, Y., et al. (2001) · Chemical Communications · doi:10.1039/b105159h · Cited by 8,358
The exciton model in molecular spectroscopy
Kasha, M., Rawls, H. R., & Ashraf El-Bayoumi, M. (1965) · Pure and Applied Chemistry · doi:10.1351/pac196511030371 · Cited by 4,253
Cited by
Hong, Y., Lam, J. W. Y., & Tang, B. Z. (2011) · Chemical Society Reviews · doi:10.1039/c1cs15113d · Cited by 6,363
Wang, J., Mei, J., Hu, R., Sun, J. Z., Qin, A., & Tang, B. Z. (2012) · Journal of the American Chemical Society · doi:10.1021/ja208883h · Cited by 593
Dong, Y., Lam, J. W. Y., Qin, A., Liu, J., Li, Z., Tang, B. Z., Sun, J., & Kwok, H. S. (2007) · Applied Physics Letters · doi:10.1063/1.2753723 · Cited by 536
Gels with sense: supramolecular materials that respond to heat, light and sound
Jones, C. D., & Steed, J. W. (2016) · Chemical Society Reviews · doi:10.1039/c6cs00435k · Cited by 487
Luminogenic polymers with aggregation-induced emission characteristics
Qin, A., Lam, J. W. Y., & Tang, B. Z. (2012) · Progress in Polymer Science · doi:10.1016/j.progpolymsci.2011.08.002 · Cited by 441
Metadata
- Authors
- Qian, Y., Li, S., Zhang, G., Wang, Q., Wang, S., Xu, H., Li, C., Li, Y., & Yang, G.
- Venue
- The Journal of Physical Chemistry B
- Publisher
- American Chemical Society (ACS)
- Published
- 2007-05-01
- Volume
- 111
- Issue
- 21
- Pages
- 5861-5868
- ISSN
- 1520-5207 (ISSN-L)
- 1520-6106
- OpenAlex
- W2042963896
- Cited by
- 224
- References
- 2
- FWCI
- 7.68
- Type
- journal article
- Language
- en
- Open access
- closed
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- Qian, Y., Li, S., Zhang, G., Wang, Q., Wang, S., Xu, H., Li, C., Li, Y., & Yang, G. (2007). Aggregation-Induced Emission Enhancement of 2-(2‘-Hydroxyphenyl)benzothiazole-Based Excited-State Intramolecular Proton-Transfer Compounds. The Journal of Physical Chemistry B. https://doi.org/10.1021/jp070076i
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