Studies on UV-Visible, Fluorescent Spectral Properties and Solvatochromic behavior of Naphthalimide Compound Containing Quaternary Ammonium

Journal: Vol. 10, No.3, 2017 - Article 3   Pages :  163 Until 172

Article Code:

H. Shaki: Golestan University - Department of Chemical Engineering

Article's abstract:

This paper presents the results of absorption spectra, fluorescence properties and the effect of solvents on UV-Vis spectra of dye quaternized 4-acetylamino-N-2-aminomethylpyridine-1,8-naphthalimide. The fluorescency of the dye was evaluated and its Stokes shift value was 6140 cm-1 in DMF. The solvatochromism behavior of the novel compound is investigated by studying its spectra in pure organic solvents of different characteristics. The factors that affect solvatochromism are discussed like solvent polarity. Finally, the fluorescent dye was applied on polyamide fabrics in order to investigate its dyeing properties. Wash, light, and rubbing fastnesses of the dyed fabrics were measured by standard methods. Moreover, the build-up properties of the synthesized dye was measured on polyamide fabrics. Dyed polyamides had very good wash and rubbing fastness degrees and moderate light fastness. The antibacterial activity of the dyed fabrics was evaluated.

Absorption spectra Fluorescence properties,Solvatochromism effect,Dyeing properties,Quaternary ammonium

1. L. G. F Patrick, A Whiting, Synthesis of some polymerisable fluorescent dyes, Dyes Pigm., 55(2002), 123-132. 2. H. Soltani Panah, A. Khosravi, K. Gharanjig, M. Khorassani, M. Khatib Zadeh, F. Afshar Taromi, Synthesis and Characterization of New Fluorescent Polymerizable Dyes Based on Naphthalimide, Iran Polym J., 19(2010), 491-500. 3. M. Hosseinnezhad, S. Moradian, K. Gharanjig, Acid azo dyes for efficient molecular photovoltaic: study of dye-sensitized solar cells performance, Prog. Color Colorants Coat., 9(2016), 61-70. 4. H. Shaki, K. Gharanjig, Sh. Rouhani, A. Khosravi, J. Fakhar, Synthesis and application of some novel antimicrobial monoazonaphthalimide dyes: synthesis and characterisation, Color. Technol., 128(2012), 270-275. 5. H. Shaki, K. Gharanjig, S. Rouhani, A. Khosravi, Synthesis and photophysical properties of some novel fluorescent dyes based on naphthalimide derivatives, J Photoch Photobio A Chem., 216(2010), 44-50. 6. A. Mohammadi, F. Golshahi, H. Ghafoori, Naphthalene-Based Azo Dyes: Synthesis, Characterization and Dyeing Performance on Polyester Fibers, Prog. Color Colorants Coat., 8(2015), 317-327. 7. R. H. Abu-Eittah, M.K.Khedr, The electronic absorption spectra of pyridine azides, solvent-solute interaction, Spectrochim. Acta A, 71(2009), 1688–1694. 8. H. Kilic, Electronic absorption study on acid-base equilibria for some keto and thioketo pyrimidine derivatives. Experimental and theoretical evidence of enolization and solute-solvent interactions, Spectrochim.Acta A, 67(2007), 1210–1219. 9. E. Ruckenstein, G.O.Berim, Effect of solute–solute and solute–solvent interactions on the kinetics of nucleation in liquids, J. Colloid Interface Sci., 342(2010), 528–532. 10. I. Banik, M.N.Roy, Study of solute–solvent interaction of some bio-active solutes prevailing in aqueous ascorbic acid solution, J. Mol. Liq., 169(2012), 8–14. 11. M. A. Rauf, J. Graham, S.B. Bukallah, M.A.S. Al-Saedi, Solvatochromic behavior on the absorption and fluorescence spectra of Rose Bengal dye in various solvents, Spectrochim.Acta A, 72(2009), 133–137. 12. A. Dogan, N. Aslan, E. Canel, E. Kilic, olvent Effects on the Protonation Constants of Some α-Amino Acid Esters in 1,4-Dioxane–Water Mixtures, J. Sol. Chem., 39(2010), 1589–1596. 13. M. A. Rauf, S. Hisaindee, Studies on solvatochromic behavior of dyes using spectral techniques, J. Mol. Struct., 1042(2013), 45–56. 14. M. A. Rauf, S. Hisaindee, J. P. Graham, M. Nawaz, Solvent effects on the absorption and fluorescence spectra of Cu(II)-phthalocyanine and DFT calculations, J. Mol. Liq., 68(2012), 102–109. 15. M. S. Masoud, S. S. Hagagg, A. E. Ali, N. M. Nasr, Solvatochromic behavior of the electronic absorption spectra of gallic acid and some of its azo derivatives, Spectrochim. Acta A, 94(2012), 256–264. 16. M. Domınguez, M. C. Rezende, Towards a unified view of the solvatochromism of phenolate betaine dyes, J. Phys. Org. Chem., 23(2010), 156–170. 17. S. Cha, M. G. Choi, H. R. Jeon, S. K. Chang, Negative solvatochromism of merocyanine dyes: Application as water content probes for organic solvents, Sens. Actuators B: Chem., 157(2011), 14–18. 18. E. Obłak, A. Piecuch, K. Guz-Regner, E. Dworniczek, Antibacterial activity of gemini quaternary ammonium salts, FEMS Microbiol Lett., 350(2014), 190–198. 19. M. Ma, G. Sun, Antimicrobial cationic dyes. Part 3: simultaneous dyeing and antimicrobial finishing of acrylic fabrics, Dyes Pigm., 66(2005), 33-41. 20. H. Shaki, A. Khosravi, K. Gharanjig, Novel Cationic Dye Based on Naphthalimide: Part 1: Synthesis, Characterization and Evaluation of Biology Efficacy as Antimicrobial Agent, Prog. Color Colorants Coat., 9(2016), 261-268. 21. J. Liu, C. C. Min, Q. G. Zhou, Y. X. Cheng, L. X. Wang, D. G. Ma, Blue light-emitting polymer with polyfluorene as the host and highly fluorescent 4-dimethylamino-1,8-naphthalimide as the dopant in the sidechain, Appl. Phys. Lett., 88(2006), 083505:1-3. 22. P. Gasiorski, K. S. Danel, M. Matusiewicz, T. Uchacz, W. Kuznik, L. Piatek, A.V. Kityk, DFT/TDDFT study on the electronic structure and spectral properties in annulated analogue of phenyl heteroazulene derivative, Mater. Chem. Phys., 132(2012), 330–338. 23. Andriy V. Kityk, Absorption and Fluorescence Spectra of Heterocyclic Isomers from Long-Range-Corrected Density Functional Theory in Polarizable Continuum Approach, J. Phys. Chem. A., 116(2012), 3048–3055. 24. H. Ulla, B. Garudachari, M. N. Satyanarayan, G. Umesh, A.M. Isloor, Blue organic light emitting materials: Synthesis and characterization of novel 1,8-naphthalimide derivatives, Opt. Mater., 36(2014), 704–711. 25. K. Gharanjig, M. Arami, H. Bahrami, B. Movassagh, N. Mohammad Mahmoodi, S. Rouhani, Synthesis, spectral properties and application of novel monoazo disperse dyes derived from N-ester-1,8-naphthalimide to polyester, Dyes Pigm., 76(2008), 684-689. 26. H. Shaki, K. Gharanjig, A. Khosravi, Spectral, dyeing and antimicrobial properties of some monoazo naphthalimide dyes on polyamide, Indian J Fibre Text Res., 40(2015), 425-430. 27. H. Shaki, K. Gharanjig, A. Khosravi, Synthesis and Investigation of Antimicrobial Activity and Spectrophotometric and Dyeing Properties of Some Novel Azo Disperse Dyes Based on Naphthalimides, Biotechnol. Prog., 31(2015), 1086–1095. 28. N. I. Georgiev, M. D. Dimitrova, Y. D. Todorova, V. Bojinov, Synthesis, chemosensing properties and logic behaviour of a novel ratiometric 1,8-naphthalimide probe based on ICT and PET, Dyes Pigm., 131(2016), 9–17. 29. M. Dodangeh, K. Gharanjig , M. Arami, A novel Ag+ cation sensor based on polyamidoamine dendrimer modified with 1,8-naphthalimide derivatives, Spectrochim. Acta A., 154(2016), 207–214. 30. A. Alimmari, D. Mijin, R. Vukićević, B. Božić, N. Valentić, V. Vitnik, Ž. Vitnik, G. Ušćumlić, Synthesis, structure and solvatochromic properties of some novel 5-arylazo-6-hydroxy-4-phenyl-3-cyano-2-pyridone dyes, Chem. Cent. J., 6(2012), 71-78. 31. M. S. Zakerhamidi, A. Ghanadzadeh, M. Moghdam, Solvent Effects on the UV/ Visible Absorption Spectra of Some Aminoazobenzene Dyes, Chem. Sci. Trans., 1(2012), 1-8. 32. E. O. Moradi Rufchahi, H. Yousefi, M. Mohammadinia, Synthesis and spectral properties of some azo disperse dyes containing a benzothiazole moiety, J. Mol. Liq., 188(2013), 173–177. 33. H. Khanmohammadi, M. Pass, K. Rezaeian, G. Talei, Solvatochromism, spectral properties and antimicrobial activities of new azo-azomethine dyes with N2S2O2 donor set of atoms, J. Mol. Struct., 1072(2014), 232-237. 34. D. Gao, A. Li, L. Guan, X. Zhang, L. Y. Wang, Solvent-dependent ratiometric fluorescent merocyanine dyes: Spectral properties, interaction with BSA as well as biological applications, Dyes Pigm., 129(2016), 163-173. 35. E. V. Sanin, A. I. Novikov, A. D. Roshal, Spectral Properties of Dyes with Interfragmental Charge Transfer: Solvatochromism and Solvatofluoro-chromism of 2-(3-Coumaroyl)-benzopyrylium Perchlorates, Int. J. Spectrosc., 2014(2014), 1-8. 36. J. Thipperudrappa, Analysis of solvatochromism of a biologically active ketocyanine dye using different solvent polarity scales and estimation of dipole moments, Int. j. life sci. pharma res., 4(2014), 1-11. 37. M Sadeghi-Kiakhani, S. Safapour, Functionalization of poly(amidoamine) dendrimer-based nano-architectures using a naphthalimide derivative and their fluorescent, dyeing and antimicrobial properties on wool fibers, Luminescence, 31(2016), 1005-1012.

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