Synthesis and photophysical properties of some novel fluorescent dyes based on naphthalimide derivatives

作者: H. Shaki , K. Gharanjig , S. Rouhani , A. Khosravi

DOI: 10.1016/J.JPHOTOCHEM.2010.09.004

关键词:

摘要: Abstract A series of novel naphthalimide dyes with amino and acetylamino functional groups were synthesized through imidation, reduction acetylation reactions on 4-nitro-1,8-naphthalic anhydride. The characterized by DSC, TLC (Rf values), FTIR, 1HNMR, 13CNMR, UV–visible Fluorometery. Molar extinction coefficients wavelength maxima obtained examining dye solutions in DMF THF. results demonstrated that the have ranging from 372 to 433 nm 370 419 nm THF molar 1.1 × 104–1.9 × 104 l mol−1 cm−1 0.84 × 104–1.4 × 104 l mol−1 cm−1 absorption spectra showed grafting N-substituted naphthalimides does not affect their color whilst type substitutions C-4 position very effectively changes color. fluorescency these was evaluated Stokes shift values determined as solutions. all had fluorescence properties between 4000 6600 cm−1 3880 cm−1 6400 cm−1 Measuring quantum yields containing N-ester group highest 4-acetylamino lowest yield.

参考文章(43)
Vladimir B. Bojinov, Ivo K. Grabchev, Novel functionalized 2-(2-hydroxyphenyl)-benzotriazole – benzo[de]isoquinoline-1,3-dione fluorescent UV absorbers Journal of Photochemistry and Photobiology A: Chemistry. ,vol. 172, pp. 308- 315 ,(2005) , 10.1016/J.JPHOTOCHEM.2004.12.020
G CHEN, L WANG, J ZHANG, F CHEN, M ANPO, Photophysical properties of a naphthalimide derivative encapsulated within Si-MCM-41, Ce-MCM-41 and Al-MCM-41 Dyes and Pigments. ,vol. 81, pp. 119- 123 ,(2009) , 10.1016/J.DYEPIG.2008.09.013
Vladimir B. Bojinov, Nikolai I. Georgiev, Peter S. Nikolov, Synthesis and photophysical properties of fluorescence sensing ester- and amidoamine-functionalized 1,8-naphthalimides Journal of Photochemistry and Photobiology A: Chemistry. ,vol. 193, pp. 129- 138 ,(2008) , 10.1016/J.JPHOTOCHEM.2007.06.016
Tomasz Martyński, Ewa Mykowska, Roland Stolarski, Danuta Bauman, Derivatives of 4-amino-N-ethylnaphthalimide for use in nematic liquid crystals Dyes and Pigments. ,vol. 25, pp. 115- 129 ,(1994) , 10.1016/0143-7208(94)85043-7
Xavier Poteau, Andrew I. Brown, Robert G. Brown, Colette Holmes, David Matthew, Fluorescence switching in 4-amino-1,8-naphthalimides: “on–off–on” operation controlled by solvent and cations Dyes and Pigments. ,vol. 47, pp. 91- 105 ,(2000) , 10.1016/S0143-7208(00)00067-X
Jian-Xin Yang, Xin-Liang Wang, Xue-Mei Wang, Long-He Xu, None, The synthesis and spectral properties of novel 4-phenylacetylene-1,8-naphthalimide derivatives Dyes and Pigments. ,vol. 66, pp. 83- 87 ,(2005) , 10.1016/J.DYEPIG.2004.07.015
Vladimir Bojinov, Galya Ivanova, Jean-Marc Chovelon, Ivo Grabchev, Photophysical and photochemical properties of some 3-bromo-4-alkylamino-N-alkyl-1,8-naphthalimides Dyes and Pigments. ,vol. 58, pp. 65- 71 ,(2003) , 10.1016/S0143-7208(03)00036-6
E. Martín, J.L.Gu. Coronado, J.J. Camacho, A. Pardo, Experimental and theoretical study of the intramolecular charge transfer on the derivatives 4-methoxy and 4-acetamide 1,8-naphthalimide N-substituted Journal of Photochemistry and Photobiology A: Chemistry. ,vol. 175, pp. 1- 7 ,(2005) , 10.1016/J.JPHOTOCHEM.2005.03.023
Vladimir B. Bojinov, Temenushka N. Konstantinova, Fluorescent 4-(2,2,6,6-tetramethylpiperidin-4-ylamino)-1,8-naphthalimide pH chemosensor based on photoinduced electron transfer Sensors and Actuators B-chemical. ,vol. 123, pp. 869- 876 ,(2007) , 10.1016/J.SNB.2006.10.035