Abstract
A method for the synthesis of N-aryl-substituted 4-amino- and 4-acetylaminonaphthalimide derivatives with mono- and dialkoxy groups or a 15-crown-5 moiety in the N-aryl substituent is described. The introduction of electron-donating alkoxy groups into the benzene ring of the N-aryl fragment results in fluorescence quenching of the naphthalimide chromophore, which is most pronounced in the spectra of N-acetyl derivatives. The photophysical properties of the synthesized 4-amino- and 4-acetylaminonaphthalimides depend on the solvent polarity and its specific solvating ability due to H-bonding. The crown-containing compounds are promising fluorescent chemosensors for metal cations.
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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 6, pp. 1199–1206, June, 2009.
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Panchenko, P.A., Fedorov, Y.V., Fedorova, O.A. et al. Synthesis and spectral properties of 4-amino- and 4-acetylamino-N-arylnaphthalimides containing electron-donating groups in the N-aryl substituent. Russ Chem Bull 58, 1233–1240 (2009). https://doi.org/10.1007/s11172-009-0160-x
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DOI: https://doi.org/10.1007/s11172-009-0160-x