Proton-Transfer Spectroscopy of 7-Azaindole Derivatives
碩士 === 國立中正大學 === 化學研究所 === 88 === Self-dimerization of 7-azaindole (7AI) has long been recognized for undergoing the excited-state double proton transfer resulting in a large Stokes shifted emission. Drastically different crystal structures between 7AI and 3-Iodo-7-azaindole (3I7AI) have been explo...
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| Format: | Others |
| Language: | zh-TW |
| Published: |
2000
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| Online Access: | http://ndltd.ncl.edu.tw/handle/66387004189824275819 |
| Summary: | 碩士 === 國立中正大學 === 化學研究所 === 88 === Self-dimerization of 7-azaindole (7AI) has long been recognized for undergoing the excited-state double proton transfer resulting in a large Stokes shifted emission. Drastically different crystal structures between 7AI and 3-Iodo-7-azaindole (3I7AI) have been explored, in which 7AI reveals an unusual hydrogen-bonded tetramer. Whereas 3I7AI in a single crystal exhibits solely the intact doubly hydrogen-bonded dimeric form in which excited-state double proton transfer (ESDPT) takes place with a negligibly small energy barrier. The results provide a prototype to investigate the intrinsic ESDPT in a single crystal environment where the structural information is well documented. In another approach, ground-state therodynamics and excited-state amine/imine tautomerism in 7-azaindoline (7AZD) mediated by the hydrogen bonding formation have been studied by means of absorption and emission spectroscopies. Proton-transfer isomers of 7AZD have been identified through syntheses and spectral characterization of various 7AZD methyl derivatives. Further supporting the previously proposed catalytic-versus-noncatalytic model for the ESDPT reaction.
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