期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 28, 期 4, 页码 -出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.202103584
关键词
excited-state intramolecular proton transfer; fluorescence; intramolecular hydrogen bonds; photobases; polymethine dyes
资金
- KAKENHI from the Japan Society for the Promotion of Science (JSPS) [18H05261]
A new design strategy for an excited-state intramolecular proton transfer (ESIPT) fluorophore capable of functioning in acidic media has been reported. By utilizing an intramolecular charge-transfer transition, the fluorophore undergoes proton transfer from the amine to the pyridine moiety in the excited state, resulting in significantly red-shifted emission wavelength and increased fluorescence quantum yield.
We report a new design strategy for an excited-state intramolecular proton transfer (ESIPT) fluorophore that can be used in acidic media. A photobasic pyridine-centered donor-acceptor-donor-type fluorophore is combined with a basic trialkylamine strap. In the presence of an acid, protonation occurs predominantly at the amine moiety in the ground state. A single-crystal X-ray diffraction analysis confirmed the formation of a pre-organized intramolecular hydrogen-bonded structure between the resulting ammonium moiety and the pyridine ring. Upon excitation, the intramolecular charge-transfer transition increases the basicity of the pyridine moiety in the excited state, resulting in proton transfer from the amine to the pyridine moiety. Consequently, the fluorophore takes on a polymethine-dye character in the ESIPT state, which gives rise to significantly red-shifted emission with an increased fluorescence quantum yield.
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