EN
Photophysics, pH Sensing and Hydrolysis Study of a Novel 1,8-Naphthalimide Derivative
Abstract
In this study, a novel highly emissive compound
was synthesized via two steps synthetic procedure and characterized by 1H-NMR,
13C-NMR and FTIR. Then its photophysical properties, pH sensing behaviours
and pH-dependent hydrolysis were systematically investigated by ultraviolet and
fluorescence spectroscopy. Photophysics studies were carried out in fourteen
common organic solvents and absorption/emission spectra were recorded in Britton Robinson buffers (pH=3-12) to determine pH sensing behaviours. From
the photophysical results, it has been shown that the novel compound exhibits
strongly solvent polarity dependent emission and has high quantum yield (up to
0.72). Furthermore, at pH=12, absorbance started to decrease while emission was
increasing and blue-shifting due to basic hydrolysis after a several minutes. Therefore,
time dependent hydrolysis was also investigated at mentioned pH.
Keywords
References
- Reference1. Atahan A, Durmus S. 1-Amino-2-hydroxy-4-naphthalenesulfonic acid based Schiff bases or naphtho[1,2-d]oxazoles: selective synthesis and photophysical properties. Spectrochimica Acta A Molecular and Bio-molecular Spectroscopy. 2015 Jun 5;144:61-7.
- Reference2. Orhan E, Gundogdu L, Kose M, Yokoyama Y. Synthesis and photochromic properties of 4,5-bisaryl-3(2H)-pyridazinones. Journal of Photochemistry and Photobiology A: Chemistry. 2016;314:164–170.
- Reference3. Yoon SA, Lee J, Lee MH. A ratiometric fluorescent probe for Zn2+ based on pyrene- appended naphthalimide-dipicolylamine. Sensors and Actuators B. 2018;258:50-5.
- Reference4. Ulla H, Kiran MR, Garudachari B, Satyanarayan MN, Umesh G, Isloor AM. Blue emitting halogen–phenoxy substituted 1,8-naphthalimides for potential organic light emitting diode applications. Optical Materials. 2014;37:311-21.
- Reference5. Li ZZ, Niu CG, Zeng GM, Liu YG, Gao PF, Huang GH, Mao YA. A novel fluorescence ratiometric pH sensor based on covalently immobilized piperazinyl-1,8-napthalimide and benzothioxanthene. Sensors and Actuators B. 2006;114:308-15.
- Reference6. Simas ER, Gehlen MH, Pinto MFS, Siqueira J, Misoguti L. Intrachain Energy Migration to Weak Charge-Transfer State in Polyfluorene End-Capped with Naphthalimide Derivative. Journal of Physical Chemistry A. 2010;114:12384–90.
- Reference7. Cao H, Chang V, Hernandez R, and Heagy M D. Matrix Screening of Substituted N-Aryl-1,8-naphthalimides Reveals New Dual Fluorescent Dyes and Unusually Bright Pyridine Derivatives. Journal of Organic Chemistry. 2005;70:4929-34.
- Reference8. Liu J, Qian Y. A novel naphthalimide-rhodamine dye: Intramolecular fluorescence resonance energy transfer and ratiometric chemodosimeter for Hg2+ and Fe3+. Dyes and Pigments. 2017;136:782-90.
Details
Primary Language
English
Subjects
Electrochemistry
Journal Section
Research Article
Publication Date
January 1, 2018
Submission Date
April 19, 2018
Acceptance Date
May 6, 2018
Published in Issue
Year 2018 Volume: 5 Number: 2
APA
Atahan, A., & Orhan, E. (2018). Photophysics, pH Sensing and Hydrolysis Study of a Novel 1,8-Naphthalimide Derivative. Journal of the Turkish Chemical Society Section A: Chemistry, 5(2), 775-784. https://doi.org/10.18596/jotcsa.414821
AMA
1.Atahan A, Orhan E. Photophysics, pH Sensing and Hydrolysis Study of a Novel 1,8-Naphthalimide Derivative. JOTCSA. 2018;5(2):775-784. doi:10.18596/jotcsa.414821
Chicago
Atahan, Alparslan, and Ersin Orhan. 2018. “Photophysics, PH Sensing and Hydrolysis Study of a Novel 1,8-Naphthalimide Derivative”. Journal of the Turkish Chemical Society Section A: Chemistry 5 (2): 775-84. https://doi.org/10.18596/jotcsa.414821.
EndNote
Atahan A, Orhan E (January 1, 2018) Photophysics, pH Sensing and Hydrolysis Study of a Novel 1,8-Naphthalimide Derivative. Journal of the Turkish Chemical Society Section A: Chemistry 5 2 775–784.
IEEE
[1]A. Atahan and E. Orhan, “Photophysics, pH Sensing and Hydrolysis Study of a Novel 1,8-Naphthalimide Derivative”, JOTCSA, vol. 5, no. 2, pp. 775–784, Jan. 2018, doi: 10.18596/jotcsa.414821.
ISNAD
Atahan, Alparslan - Orhan, Ersin. “Photophysics, PH Sensing and Hydrolysis Study of a Novel 1,8-Naphthalimide Derivative”. Journal of the Turkish Chemical Society Section A: Chemistry 5/2 (January 1, 2018): 775-784. https://doi.org/10.18596/jotcsa.414821.
JAMA
1.Atahan A, Orhan E. Photophysics, pH Sensing and Hydrolysis Study of a Novel 1,8-Naphthalimide Derivative. JOTCSA. 2018;5:775–784.
MLA
Atahan, Alparslan, and Ersin Orhan. “Photophysics, PH Sensing and Hydrolysis Study of a Novel 1,8-Naphthalimide Derivative”. Journal of the Turkish Chemical Society Section A: Chemistry, vol. 5, no. 2, Jan. 2018, pp. 775-84, doi:10.18596/jotcsa.414821.
Vancouver
1.Alparslan Atahan, Ersin Orhan. Photophysics, pH Sensing and Hydrolysis Study of a Novel 1,8-Naphthalimide Derivative. JOTCSA. 2018 Jan. 1;5(2):775-84. doi:10.18596/jotcsa.414821
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