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Hydrogen-Bonding-Induced Phenomena in Bifunctional Heteroazaaromatics
Abstract
Ground and excited state processes induced by hydrogen bond formation are discussed for a family of heterocyclic compounds which possess both a proton donor (pyrrole NH group) and an acceptor (pyridine-type nitrogen). Excited state double proton transfer and rapid S(0) <-- S(1) internal conversion are observed only for molecules capable of forming cyclic, multiply hydrogen-bonded complexes. If the 1:1 cyclic, doubly hydrogen-bonded solvate is present in the ground state, the phototautomerization occurs even in rigid solvents at low temperatures. Internal conversion process requires solvent rearrangement and, therefore, does not proceed in a rigid environment. Another type of fluorescence quenching was also detected, involving photoinduced electron transfer from an excited chromophore to an aromatic hydrogen-bonded acceptor, such as pyridine. In molecules consisting of proton donor and acceptor units linked by a single bond, syn-anti rotamerization caused by hydrogen bonding is observed.
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Cited by
Hsieh, C.-C., Jiang, C.-M., & Chou, P.-T. (2010) · Accounts of Chemical Research · doi:10.1021/ar1000499 · Cited by 383
Excited-state proton transfer relieves antiaromaticity in molecules
Wu, C.-H., Karas, L. J., Ottosson, H., & Wu, J. I.-C. (2019) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.1908516116 · Cited by 110
Dereka, B., & Vauthey, E. (2017) · Chemical Science · doi:10.1039/c7sc00437k · Cited by 82
Metadata
- Authors
- Waluk, J.
- Venue
- Accounts of Chemical Research
- Publisher
- American Chemical Society (ACS)
- Published
- 2003-08-23
- Volume
- 36
- Issue
- 11
- Pages
- 832-838
- ISSN
- 0001-4842 (ISSN-L)
- 1520-4898
- OpenAlex
- W2154970920
- Cited by
- 190
- References
- 0
- FWCI
- 5.80
- Type
- journal article
- Language
- en
- Open access
- closed
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- Waluk, J. (2003). Hydrogen-Bonding-Induced Phenomena in Bifunctional Heteroazaaromatics. Accounts of Chemical Research. https://doi.org/10.1021/ar0200549
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