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Excited-State Intramolecular Proton Transfer in Five-Membered Hydrogen-Bonding Systems: 2-Pyridyl Pyrazoles
Abstract
The excited-state intramolecular proton transfer (ESIPT) reaction in five-membered N-H...N hydrogen-bonding systems has been explored through design and syntheses of a series of 5-(2-pyridyl) 1-H-pyrazoles 1a-d. The ESIPT mechanism was confirmed through spectroscopy, relaxation dynamics, and corresponding methylated analogues. The results demonstrate for the first time a unique system among ESIPT molecules, in which ESIPT incorporates an appreciably large energy barrier fine-tuned by the skeletal reorganization. This makes 1a-d systems ideal models for probing the reaction potential energy surface.
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Citations
Cited by
Proton-coupled electron transfer
Huynh, M. H. V., & Meyer, T. J. (2007) · Chemical Reviews · doi:10.1021/cr0500030 · Cited by 1,659
Hsieh, C.-C., Jiang, C.-M., & Chou, P.-T. (2010) · Accounts of Chemical Research · doi:10.1021/ar1000499 · Cited by 383
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Metadata
- Authors
- Yu, W.-S., Cheng, C.-C., Cheng, Y.-M., Wu, P.-C., Song, Y.-H., Chi, Y., & Chou, P.-T.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2003-08-14
- Volume
- 125
- Issue
- 36
- Pages
- 10800-10801
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2043694157
- Cited by
- 178
- References
- 0
- FWCI
- 4.17
- Type
- journal article
- Language
- en
- Open access
- closed
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- CoChat. (2026). Citation check: Excited-State Intramolecular Proton Transfer in Five-Membered Hydrogen-Bonding Systems: 2-Pyridyl Pyrazoles. https://app.cochat.ai/papers/10.1021/ja035382y
- The paper
- Yu, W.-S., Cheng, C.-C., Cheng, Y.-M., Wu, P.-C., Song, Y.-H., Chi, Y., & Chou, P.-T. (2003). Excited-State Intramolecular Proton Transfer in Five-Membered Hydrogen-Bonding Systems: 2-Pyridyl Pyrazoles. Journal of the American Chemical Society. https://doi.org/10.1021/ja035382y
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Contains information from the Semantic Scholar Academic Graph Datasets, made available under the ODC Attribution License (ODC-BY 1.0).
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