Synthesis and spectral properties of novel chlorinated pH fluorescent probes

Eight chlorinated fluoresceins have been synthesized by the reaction of chlorinated resorcinols with 4, 5, 6, 7-tetrachlorophthalic anhydride or 3, 6-dichloro-4-carboxyphthalic anhydride in the presence of methanesulfonic acid. The spectral properties of the chlorinated fluoresceins were studied. It...

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Bibliographic Details
Published in:Journal of luminescence 2011-04, Vol.131 (4), p.776-780
Main Authors: Wu, Xiang-long, Jin, Xi-lang, Wang, Yun-xia, Mei, Qi-bing, Li, Jian-li, Shi, Zhen
Format: Article
Language:English
Subjects:
Anhydrides
Biological and medical sciences
Chlorinated fluorescein
Chlorination
Chlorine
Emission
Fluorescein
Fluorescent probe
Luminescence
Medical sciences
pH probe
Quantum yield
Radiotherapy. Instrumental treatment. Physiotherapy. Reeducation. Rehabilitation, orthophony, crenotherapy. Diet therapy and various other treatments (general aspects)
Spectra
Spectral properties
Synthesis
Technology. Biomaterials. Equipments. Material. Instrumentation
Wavelengths
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Summary:Eight chlorinated fluoresceins have been synthesized by the reaction of chlorinated resorcinols with 4, 5, 6, 7-tetrachlorophthalic anhydride or 3, 6-dichloro-4-carboxyphthalic anhydride in the presence of methanesulfonic acid. The spectral properties of the chlorinated fluoresceins were studied. It was found that they have absorption and emission maxima at long wavelengths and high fluorescence quantum yields. Emission spectra of chlorinated fluoresceins shifted towards long wavelength with increase in chlorine. pH-dependent properties of chlorinated fluoresceins were studied in detail. These compounds showed a strongly pH-sensitive range of 3.0–7.0. These chlorinated fluoresceins will be used as pH probes for pH measurement of the cell because of the high quantum yield and strong pH-sensitivity. ► Eight chlorinated fluoresceins have been synthesized in the presence of methanesulfonic acid. ► Emission spectra of these compounds shifted towards long wavelength with increase in chlorine. ► Eight chlorinated fluoresceins showed a strongly pH-sensitive range of 3.0–7.0. ► They have emission maxima at long wavelengths and high fluorescence quantum yields.
ISSN:0022-2313
1872-7883
DOI:10.1016/j.jlumin.2010.12.001