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Volume 17, Issue 1 (Winter-Spring 2023)
IJOP 2023, 17(1): 11-20 |
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Khadem Sadigh M. Environment Polarity Effects on Spectral Properties and Dipole Moments of Fluorescein Disodium. IJOP 2023; 17 (1) :11-20
URL: http://ijop.ir/article-1-533-en.html
URL: http://ijop.ir/article-1-533-en.html
Department of Laser and Optical Engineering, University of Bonab, Bonab, Iran
Abstract: (1184 Views)
Xanthene and its derivatives are important in medical diagnosis and laser technology. In this work, spectral features of fluorescein disodium were investigated in different environments with different polarity characteristics. Hence, the absorption and fluorescence spectra of this molecule were studied in different environments. Our results show that spectral features of fluorescein disodium depend strongly on substituents in its structure and molecular interactions. To investigate the contribution of various molecular interactions on the spectral behavior of the used sample, the linear solvation energy relationship concept is used. Moreover, the dipole moment variations from ground to excited states were estimated using molecular spectral features in different solvent media. According to the results, the dipole moment value in the excited state is higher than that in the ground state.
Type of Study: Research |
Subject:
Spectroscopy
Received: 2023/04/20 | Revised: 2024/05/28 | Accepted: 2023/07/26 | Published: 2023/07/28
Received: 2023/04/20 | Revised: 2024/05/28 | Accepted: 2023/07/26 | Published: 2023/07/28
References
1. C. Reichardat, Solvents and solvent effects in organic chemistry, 2nd Ed. VCH, New York, 1988.
2. J.E. Puskas, G. Shrikhande, and K. Molnar, "Synthesis and characterization of four functional fluoresceins," J. Mol. Liq., Vol. 381, pp. 121747 (1-8), 2023. [DOI:10.1016/j.molliq.2023.121747]
3. N.O. Mchedlov-Petrossyan, S.V. Shekhovtsov, E.G. Moskaeva, I.V. Omelchenko, A.D. Roshal, and A.O. Doroshenko, "New fluorescein dyes with unusual properties: Tetra- and pentanitrofluoresceins," J. Mol. Liq., Vol. 367, pp. 120541 (1-13), 2022. [DOI:10.1016/j.molliq.2022.120541]
4. S.A. Wagay, M. Alam, and R. Ali, "Synthesis of two novel fluorescein appended dipyromethanes (DPMs): Naked-dye chemosensors for fluoride, acetate and phosphate anions," J. Mol. Struct., Vol. 1291, pp. 135982 (1-7), 2023. [DOI:10.1016/j.molstruc.2023.135982]
5. M. Murariu and L. Stroea, "Increasing detection sensitivity of fluorescent polymeric sensors containing fluorescein derivatives by Au NPs," Spectrochim Acta A, Vol. 291, pp. 122279 (1-14), 2023. [DOI:10.1016/j.saa.2022.122279] [PMID]
6. L. Niu, J. Liu, S. Gao, J. Gao, Y. Zhou, S. Liu, C. Ma, and Y. Zhao, "Fluoride ions detection in aqueous media by unprecedented ring opening of fluorescein dye: A novel multimodal sensor for fluoride ions and its utilization in live cell imaging," Spectrochim Acta A, Vol. 287, pp. 122001 (1-8), 2023. [DOI:10.1016/j.saa.2022.122001] [PMID]
7. A.E. Likhonina, G.M. Mamardashvili, N.Z. Mamardashvili, "Photoactive porphyrin-fluorescein arrays to control the acidity of medium," Spectrochim Acta A, Vol. 424, pp. 113650 (1-10), 2022. [DOI:10.1016/j.jphotochem.2021.113650]
8. M. Khadem Sadigh and M.S. Zakerhamidi, "Solvent polarity sensitive characteristics of various tautomers of azo compounds: linear and nonlinear optical properties," Spectrochim Acta A, Vol. 239, pp. 118445 (1-12), 2020. [DOI:10.1016/j.saa.2020.118445] [PMID]
9. M. Khadem Sadigh and M.S. Zakerhamidi, "Media polarity and concentration roles on the third order nonlinear behaviors of thiazine dyes," Opt. Laser. Technol., Vol. 100, pp. 216-224, 2018. [DOI:10.1016/j.optlastec.2017.10.007]
10. M. Khadem Sadigha, A.N. Shamkhali, R. Teimuri-Mofradd, S. Mozaffarnia, and K. Rahimpour "Polarity effects on the optical responses of some biologically active molecules with different substituents,", J. Mol. Struct., Vol. 1269, pp. 133787 (1-11), 2022. [DOI:10.1016/j.molstruc.2022.133787]
11. D. Magde, G.E. Rojas, and P.G. Seybold, "Solvent dependence of the fluorescence lifetimes of xanthene dyes," Photochem. Photobiol., Vol. 70, pp. 737-744, 1999. [DOI:10.1111/j.1751-1097.1999.tb08277.x]
12. D.S. Pellosi, B.M. Estevao, J. Semensato, D. Severino, M.S. Baptista, M.J. Politi, N. Hioka, and W. Caetano, "Photophysical properties and interactions of xanthene dyes in aqueous micelles," J. Photochem. Photobiol A, Vol. 247, pp. 8-15, 2012. [DOI:10.1016/j.jphotochem.2012.07.009]
13. C. Zhang, J. Wu, W. Liu, W. Zhang, C-S. Lee, and P. Wang, "NIR-II xanthene dyes with structure-inherent bacterial targeting for efficient photothermal and broad-spectrum antibacterial therapy," Acta Biomater., Vol. 159, pp. 247-258, 2023. [DOI:10.1016/j.actbio.2023.01.031] [PMID]
14. O. Karaman, G. Atakan Alkan, C. Kizilenis, C. Ceren Akgul, and G. Gunbas, "Xanthene dyes for cancer imaging and treatment: A material odyssey," Coord. Chem. Rev., Vol. 475, pp. 214841 (1-45), 2023. [DOI:10.1016/j.ccr.2022.214841]
15. H. Wang, G. Zhou, C. Mao, and X. Chen, "A fluorescence sensor bearing nitroolefin moiety for the detection of thiols and its biological imaging," Dyes Pigments., Vol. 96, pp. 232-236, 2013. [DOI:10.1016/j.dyepig.2012.07.013]
16. A. Nakamura and S. Tsukiji, "Ratiometric fluorescence imaging of nuclear pH in living cells using Hoechst-tagged fluorescein," Bioorg. Chem. Lett., Vol. 27, pp. 3127-3130, 2017. [DOI:10.1016/j.bmcl.2017.05.036] [PMID]
17. K. Minkin, E. Naydenov, K. Gabrovski, P. Dimova, M. Penkov, R. Tanova, S. Nachev, and K. Romanski, "Intraoperative fluorescein staining for benign brain tumors," Clin. Neurol. Neurosurg., Vol. 149, pp. 22-26, 2016. [DOI:10.1016/j.clineuro.2016.07.016] [PMID]
18. N. Klonis, A.H.A. Clayton, E.W. Voss, Jr, and W.H. Sawyer, "Spectral properties of fluorescein in solvent-water mixtures: applications as a probe of Hydrogen bonding environments in biological systems," Photochem. Photobiol., Vol. 67, pp. 500-510, 1998. [DOI:10.1111/j.1751-1097.1998.tb09085.x] [PMID]
19. B. Acemioglu, M. Arik, H. Efeoglu, and Y. Onganer, "Solvent effect on the ground and excited state dipole moments of fluorescein," J. Mol. Struct. (Theochem)., Vol. 548, pp. 165-171, 2001. [DOI:10.1016/S0166-1280(01)00513-9]
20. B.B. Bhowmik and P. Ganguly, "Photophysics of xanthene dyes in surfactant solution," Spectrochim Acta A, Vol. 61, pp. 1997-2003, 2005. [DOI:10.1016/j.saa.2004.07.031] [PMID]
21. R. Sariri, M.S. Zakerhamidi, K. Baharpaima, and A. Ghanadzadeh, "The anion effect and molecular association of rhodamine dyes in isotropic and anisotropic solvents," J. Mol. Liq., Vol. 115, pp. 55-61, 2004. [DOI:10.1016/j.molliq.2003.12.024]
22. E. Slyusareva, A. Sizykh, A. Tyagi, and A. Penzkofer, "Spectral and photophysical properties of fluorone dyes in bio-related films and methanol," J. Photochem Photobiol A, Vol. 208, pp. 131-140, 2009. [DOI:10.1016/j.jphotochem.2009.09.006]
23. S. De, S. Das, and A. Girigoswami, "Environment effects on the aggregation of some xanthene dyes used in lasers," Spectrochim Acta A, Vol. 61, pp. 1821-1833, 2005. [DOI:10.1016/j.saa.2004.06.054] [PMID]
24. M.J. Abboud, M.J. Kamlet, and R.W. Taft, "Regarding a generalized scale of solvent polarities," J. Am. Chem. Soc., Vol. 99, pp. 8325-8327, 1977. [DOI:10.1021/ja00467a039]
25. M.J. Kamlet and R.W. Taft, "The solvatochromic comparison method. I. The Beta-scale of solvent hydrogen-bond acceptor (HBA) basicities," J. Am. Chem. Soc., Vol. 98, pp. 377-383, 1976. [DOI:10.1021/ja00418a009]
26. M.J. Kamlet and R.W. Taft, "Linear solvation energy relationships. 3. Some re-interpretations of solvent effects based on correlations with solvent pi-star and alpha values," J. Chem. Soc., Perkin Trans. Vol. 2, pp. 349-356, 1979. [DOI:10.1039/P29790000349]
27. N. Klonis, A.H.A. Clayton, E.W. Voss, and W.H. Sawyer, "Spectral properties of fluorescein in solvent-water mixtures: applications as a probe of hydrogen bonding environments in biological systems," J. Photochem. Photobiol., Vol. 67, pp. 500-510, 1998. [DOI:10.1111/j.1751-1097.1998.tb09085.x] [PMID]
28. A. Kawaski, Progress in Photochemistry and Photophysics, Boca Raton, Boston, pp. 1-47, 1992.
29. A. Kawski, "The influence of polar molecules on the electron spectra of 4-aminophthalimide," Acta. Phys. Pol., Vol. 25, pp. 285-290, 1964.
30. J. Kabatc, B. Osmialowski, and J. Paczkowski, "The experimental studies on the determination of ground and excited state dipole moments of some hemicyanine dyes," Spectrochim Acta A, Vol. 63, pp. 524-531, 2006. [DOI:10.1016/j.saa.2005.05.039] [PMID]
31. V.R. Batistela, J.C. Cedran, H.P.M. Oliveria, I.S. Scarminio, L.T. Ueno, A.E.H. Machado, and N. Hioka, "Protolytic fluorescein species evaluated using chemometry and DFT studies," Dyes. Pigm., Vol. 86, pp. 15-24, 2010. [DOI:10.1016/j.dyepig.2009.11.002]
32. R. Sjöback, J. Nygren, and M. Kubista, "Absorption and fluorescence properties of fluorescein," Spectrochim Acta A, Vol. 51, pp. L7-L21, 1995. [DOI:10.1016/0584-8539(95)01421-P]
33. J. R. Lakowicz, Principles of fluorescence spectroscopy, Springer: USA, Chap. 6, p. 210, 2006. [DOI:10.1007/978-0-387-46312-4]
34. M.S. Zakerhamidi, M. Moghadam, A. Ghanadzadeh, and S. Hosseini, "Anisotropic and isotropic solvent effects on the dipole moment and photophysical properties of rhodamine dyes," J. Lumin., Vol. 132, pp. 931-937, 2012. [DOI:10.1016/j.jlumin.2011.11.027]
35. F. Naderi, A. Farajtabar, and F. Gharib, "Solvatochromic and preferential solvation of fluorescein in some water-alcoholic mixed solvents," J. Mol. Liq., Vol. 190, pp. 126-132, 2014. [DOI:10.1016/j.molliq.2013.10.028]
36. A. Cezarina Morosanu, D. Gheorghe Dimitriu, and D. Ortansa Dorohoi, "Excited state dipole moment of the fluorescein molecule estimated from electronic absorption spectra," J. Mol. Struct., Vol. 1180, pp. 723-732, 2019. [DOI:10.1016/j.molstruc.2018.12.057]
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