Abstract
Anthracene molecule possesses remarkable optical activity and till today this molecule is of special interest of scientists. Present study is focused on the study of effects of Chloride, Sulfate, Nitrate and Ferrate salts on absorption and emission spectra of targeted fluorophore in carbontetrachloride, chloroform, dichloromethane and methanol. Prominent solvatochromic effects shows dependence of HOMO–LUMO orbitals on solvent polarity. Anthracene molecules exhibits changes in absorption and emission spectra, and show both ON and ON–OFF behavior on addition of said ions. Based on experimental results it was concluded that fluorophore molecule could be used more effectively as UV–Visible (UV-V) sensors in comparison to the emission sensor.
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References
Barraza-Jimenez D, Flores-Hidalgo A, Glossman-Mitnik D (2009) Theoretical analysis of anthracene and its carbonyl and carboxyl derivatives using DFT and TD-DFT. J Mol Struct (Thoechem) 894(1):64–70
Lara-Severino Rdel C et al (2016) Determination of the residual anthracene concentration in cultures of haloalkalitolerant actinomycetes by excitation fluorescence, emission fluorescence, and synchronous fluorescence: Comparative study. J Anal Methods Chem 2016:6287931
Irshad R, Asim S, Mansha A, Arooj Y (2023) Naphthalene and its derivatives: Efficient fluorescence probes for detecting and imaging purposes. J Fluoresc 33(4):1273–1303. https://doi.org/10.1007/s10895-023-03153
Tigoianu R, Dorohoi DO, Airinei A (2009) Solvent influence on the electronic absorption spectra of anthracene. Rev de Chim 60(1):42–44
Fatima S et al (2022) Absorption spectra of coumarin and its derivatives. Chem Pap 76(2):627–638
Huda ZU et al (2022) Effect of pH on fluorescence spectra of coumarin derivatives. J Fluoresc 32(1):57–66
de Melo JS et al (2005) Singlet and triplet energy transfer in a bichromophoric system with anthracene covalently linked through sulfonamide to a meso-tetraphenylporphyrin. J Photochem Photobiol A Chem 172(2):151–160
Saito Y et al (2008) Anthracene based base-discriminating fluorescent oligonucleotide probes for SNPs typing: synthesis and photophysical properties. Bioorg Med Chem 16(1):107–113
Filpponen I, Sadeghifar H, Argyropoulos DS (2011) Photoresponsive cellulose nanocrystals. Nanomater Nanotechnol 1:7
Na EJ et al (2013) Non-doped blue OLEDs based on 9,9′-dimethylfluorene containing 10-naphthylanthracene derivatives. Mol Cryst Liq Cryst 584(1):113–122
Baviera GS, Donate PM (2021) Recent advances in the syntheses of anthracene derivatives 17:2028–2050
Fahmy HM et al (2018) Spectroscopic study of solvent polarity on the optical and photo-physical properties of novel 9,10-bis(coumarinyl)anthracene. J Fluoresc 28(6):1421–1430
Asim S et al (2014) Spectral and thermodynamic properties for the exciplexes of N-alkyl carbazoles with dicyanobenzenes in THF. Spectrochim Acta Part A Mol Biomol Spectrosc 118:138–145
Ali M et al (2009) Hydrogen-bond-induced microstructural transition of ionic micelles in the presence of neutral naphthols: pH dependent morphology and location of surface activity. J Phys Chem B 113(47):15563–15571
Qazi MA et al (2013) An excellent copper selective chemosensor based on calix[4]arene framework. Anal Chim Acta 761:157–168
Liu Y et al (2020) Insight into effects of molten KNO3-NaNO2-NaNO3 volumetric absorption of solar radiation from different factors by absorption spectroscopy. J Mol Liq 301:110604
Garci A et al (2020) Mechanical-bond-induced exciplex fluorescence in an anthracene-based homo[2]catenane. J Am Chem Soc 142(17):7956–7967
Xu L et al (2018) Substitution position modulating the photophysical properties of anthracene derivatives based on Tröger’s base. Tetrahedron 74(36):4738–4745
Xu J et al (2017) A family of multi-color anthracene carboxyimides: Synthesis, spectroscopic properties, solvatochromic fluorescence and bio-imaging application. Dyes Pigm 139:166–173
Christ RD, Wernli RL (2014) Chapter 12 - Sensor Theory. In: Christ RD, Wernli RL (eds) The ROV Manual (Second Edition). Butterworth-Heinemann, Oxford, pp 297–326
Saravanan P, Jayamoorthy K, Kumar SA (2015) Switch-On fluorescence and photo-induced electron transfer of 3-aminopropyltriethoxysilane to ZnO: Dual applications in sensors and antibacterial activity. Sens Actuators B Chem 221:784–791
Suresh S, Jayamoorthy K, Karthikeyan S (2018) Switch-on fluorescence of 5-amino-2-mercapto benzimidazole by Mn3O4 nanoparticles: Experimental and theoretical approach. J Lumin 198:28–33
Selvaraj SK et al (2022) 21 - Wireless nanosensor network for irrigation control. Nanosens Smart Agric, A. Denizli, et al., Editors. Elsevier. p. 463–478
Kang Z et al (2022) Smart COD sensor using UV–Vis spectroscopy against optical window surface contamination. Measurement 187:110125
Mirsky VM (2008) Chapter 18 - spreader-bar structures as molecular templates for electrochemical synthesis of nanoparticles. In: Corain B, Schmid G, Toshima N (eds) Metal Nanoclust Catal Mater Sci. Elsevier, Amsterdam, pp 321–325
Prakash SM et al (2016) Fluorescence tuning of 2-(1H-Benzimidazol-2-yl)phenol-ESIPT process. J Lumin 172:304–308
Jayabharathi J, Thanikachalam V, Jayamoorthy K (2013) Synthesis of some fluorescent benzimidazole derivatives using cobalt(ii) hydroxide as highly efficient catalyst — spectral and physico-chemical studies and ESIPT process. Photochem Photobiol Sci 12(10):1761–1773
Jayabharathi J, Thanikachalam V, Jayamoorthy K (2012) Effective fluorescent chemosensors for the detection of Zn2+ metal ion. Spectrochim Acta Part A Mol Biomol Spectrosc 95:143–147
Karunakaran C et al (2012) Photosensitization of imidazole derivative by ZnO nanoparticle. J Fluoresc 22(4):1047–1053
Karunakaran C et al (2012) Inhibition of fluorescence enhancement of benzimidazole derivative on doping ZnO with Cu and Ag. J Photochem Photobiol, A 247:16–23
Saravanan P, Jayamoorthy K, Anandakumar S (2016) Fluorescence quenching of APTES by Fe2O3 nanoparticles – Sensor and antibacterial applications. J Lumin 178:241–248
Suresh S et al (2016) Switch-Off fluorescence of 5-amino-2-mercapto benzimidazole with Ag3O4 nanoparticles: Experimental and theoretical investigations. Sens Actuators B Chem 225:463–468
Jayabharathi J et al (2012) Solvatochromic studies of fluorescent azo dyes: Kamlet-Taft (π*, α and β) and catalan (Spp, SA and SB) solvent scales approach. J Fluoresc 22(1):213–221
Anbuselvan C et al (2012) Physico-chemical studies on some fluorescence sensors: DFT based ESIPT process. Spectrochim Acta Part A Mol Biomol Spectrosc 97:125–130
Jayabharathi J et al (2014) Estimation of excited state dipolemoments from solvatochromic shifts-effect of pH. J Fluoresc 24(2):599–612
Jayabharathi J et al (2013) Synthesis, spectral studies and solvatochromism of some novel benzimidazole derivatives – ESIPT process. Spectrochim Acta Part A Mol Biomol Spectrosc 105:223–228
Karunakaran C et al (2012) Sensing rutile TiO2 through fluorescence of imidazole derivative. Sens Actuators B Chem 168:263–270
Schaschke C (2014) A dictionary of chemical engineering, ed. I.C.E. Neil Atkinson. Oxford
Senthilkumar S, Nath S, Pal H (2004) Photophysical properties of coumarin-30 dye in aprotic and protic solvents of varying polarities¶. Photochem Photobiol 80(1):104–111
Omary MA, Patterson HH (2017) Luminescence, Theory. In: Lindon JC, Tranter GE, Koppenaal DW (eds) Encyclopedia of Spectroscopy and Spectrometry (Third Edition). Academic Press, Oxford, pp 636–653
Tigoianu IR, Dorohoi DO, Airinei A (2009) Solvent influence on the electronic absorption spectra of anthracene. Rev Chim 60(1):42–44
Yang H, Rasmuson ÅC (2010) Solubility of butyl paraben in methanol, ethanol, propanol, ethyl acetate, acetone, and acetonitrile. J Chem Eng Data 55(11):5091–5093
Belova AS et al (2021) Solvent-controlled intramolecular excimer emission from organosilicon derivatives of naphthalene. Tetrahedron 93:132287
Shi B et al (2019) Excited states and excitonic interactions in prototypic polycyclic aromatic hydrocarbon dimers as models for graphitic interactions in carbon dots. Phys Chem Chem Phys 21(18):9077–9088
Sahi S et al (2018) Wavelength-shifting properties of luminescence nanoparticles for high energy particle detection and specific physics process observation. Sci Rep 8(1):10515
Chouk R, Bergaoui M, Khalfaoui M (2018) On the optoelectronic properties of non-covalently functionalized graphene for solar cell application. J Comput Electron 17(2):791–809
Vorona MY et al (2019) Developing 9,10-anthracene derivatives: Optical, electrochemical, thermal, and electrical characterization. Materials 12(17):2726
Kayama A, Shimizu A, Shintani R (2021) Anthracene-based zwitterion with a small HOMO–LUMO energy gap. Synthesis 53(21):4042–4047
Nishiuchi T, Kisaka K, Kubo T (2021) Synthesis of anthracene-based cyclic π-clusters and elucidation of their properties originating from congested aromatic planes. Angew Chem Int Ed 60(10):5400–5406
González I et al (2020) Studies on the solvatochromic effect and NLO response in new symmetric bimetallic Rhenium compounds. Polyhedron 187:114679
Fatima S, Mansha A, Asim S (2022) Computational studies followed by effect of solvent polarity and salts on HOMO–LUMO gap of 7-hydroxy coumarine notabally reflected by absorption and emission spectra. J Fluoresc 32(6):2351–2362
Hamlin JD, Phillips DAS, Whiting A (1999) UV/Visible spectroscopic studies of the effects of common salt and urea upon reactive dye solutions. Dyes Pigm 41(1):137–142
Loisel G et al (2021) Ionic strength effect on the formation of organonitrate compounds through photochemical degradation of vanillin in liquid water of aerosols. Atmos Environ 246:118140
Chen W, Zhu T (2014) Formation of nitroanthracene and anthraquinone from the heterogeneous reaction between NO2 and anthracene adsorbed on NaCl particles. Environ Sci Technol 48(15):8671–8678
Kan L et al (2019) Anthracene dimer crosslinked polyurethanes as mechanoluminescent polymeric materials. New J Chem 43(6):2658–2664
Ma C et al (2007) Synthesis and hypochromic effect of phthalocyanines and metal phthalocyanines. Dyes Pigm 74(1):141–147
Tong A et al (2020) Study on the shift of ultraviolet spectra in aqueous solution with variations of the solution concentration. Spectrochim Acta Part A Mol Biomol Spectrosc 234:118259
Ghana P et al (2020) Reduced arene complexes of scandium. Chem A Eur J 26(45):10290–10296
Mäntele W, Deniz E (2017) UV–VIS absorption spectroscopy: Lambert-Beer reloaded. Spectrochim Acta Part A Mol Biomol Spectrosc 173:965–968
Karoui R (2018) Spectroscopic technique: Fluorescence and ultraviolet-visible (UV-Vis) spectroscopies. Modern techniques for food authentication. Elsevier, pp 219–252
Guo Y et al (2019) Studies of the effect of halide ions on the fluorescence of quinine sulfate. Luminescence 34(4):450–455
Kivrak A et al (2017) Synthesis and solar-cell applications of novel furanyl-substituted anthracene derivatives. Opt Mater 73:206–212
Modukuru NK et al (2006) Tuning the DNA binding modes of an anthracene derivative with salt. J Photochem Photobiol A 177(1):43–54
Peter Pappas S, Tilley MG, Pappas BC (2003) Anthracene-bound sulfonium salts: highly efficient photoinitiators for cationic polymerization: A new synthesis of sulfonium salts which avoids the use of silver salts. J Photochem Photobiol A Chem 159(2):161–171
Haldar R et al (2016) Luminescent metal-organic complexes of pyrene or anthracene chromophores: Energy transfer assisted amplified exciplex emission and Al3+ sensing. Cryst Growth Des 16(1):82–91
Sayin S (2021) Synthesis of new anthracene-substituted calix[4]triazacrown-5 as highly sensitive fluorescent chemosensor and extractant against hazardous dichromate anion. Luminescence 36(7):1716–1724
Das A et al (2021) Dynamics of anthracene excimer formation within a water-soluble nanocavity at room temperature. J Am Chem Soc 143(4):2025–2036
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Concept and design of this article is collective contribution of all authors. They all read and approve the final manuscript of this research article. Zakia Kausar along with Sadia Asim plays a vital role in performing experimental analysis regarding the absorption and emission studies with the help of UV–Visible and Fluorescence spectroscopies. Literature survey was done by Asim Mansha. The first draft of manuscript was written by Zakia Kausar which was later refined by Sadia Asim and Asim Mansha.
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The research article entitled “Effect of Chloride, Sulfate, and Ferrate salts on Electronic Energy levels of Anthracene Proving it a Potential Candidate as an ON and ON–OFF UV–Vis Sensor.”: is carried out with the financial help from Higher Education Commission, Pakistan (Project number: 9922). All the authors involved in the write up of this article do not have any conflict of Interest.
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Kausar, Z., Mansha, A. & Asim, S. Effect of Chloride, Sulfate, and Ferrate Salts on Electronic Energy Levels of Anthracene Proving it a Potential Candidate as an ON and ON–OFF UV–Vis Sensor. J Fluoresc 34, 1365–1378 (2024). https://doi.org/10.1007/s10895-023-03363-4
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DOI: https://doi.org/10.1007/s10895-023-03363-4