Preparation, spectroscopic, cyclic voltammetry and DFT/TD-DFT studies on fluorescein charge transfer complex for photonic applications

ABSTRACT. The solid charge transfer (CT) complexes of fluorescein (Flu) with definite acceptors (tetrafluoro para benzoquinone (Fla); 7,7,8,8-tetracyanoquinodimethane (TCNQ); 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) and iodine) were prepared. Several characteristic analytic procedures such as transmission (FT-IR), diffuse reflectance, UV-Vis absorption, and cyclic voltammetry were used to determine the structural and optical properties of the prepared fluorescein charge transfer complex. Kubelka Munk model (K-M) and the absorption spectral fitting (ASF) methods were used to obtain the optical transitions of the solid fluorescein charge transfer complex and fluorescein CT complexes in methanol solution. The cyclic voltammetry method has been presented as capable of obtaining valuable information on quasi-reversible redox systems in the fluorescein CT-complexes. The electrochemical gap of the fluorescein CT complex was successfully determined from the cyclic voltammetry technique. Theoretical calculations (density functional theory) were made to corroborate experimental results for the synthesized CT complexes.   KEY WORDS: Fluorescein charge transfer complex, Optical spectroscopy, Cyclic voltammetry Bull. Chem. Soc. Ethiop. 2023, 37(2), 515-532.                                                               DOI: https://dx.doi.org/10.4314/bcse.v37i2.19

[1]  A. Hassanien,et al.  Studying spectroscopic, cyclic voltammetry, electrical properties of novel 4-amino antipyrine derivative for photonic applications , 2022, Journal of Molecular Structure.

[2]  A. Hassanien,et al.  Supramolecular charge-transfer complex generated by the interaction between tin(II) 2,3-naphtalocyanine as a donor with DDQ as an acceptor: Spectroscopic studies in solution state and theoretical calculations , 2022, Journal of Molecular Liquids.

[3]  L. Al-Harbi,et al.  Spectroscopic and Physicochemical Studies on 1,2,4-Triazine Derivative , 2022, Coatings.

[4]  A. Hassanien,et al.  Exploring microstructural, optical, electrical, and DFT/TD-DFT studies of boron subphthalocyanine chloride for renewable energy applications , 2022, Optik.

[5]  Jungkyu K. Lee,et al.  Photoinduced radical polymerization by methyl fluoresceins under visible light and the application to signal amplification of hydrogen peroxide , 2022, Dyes and Pigments.

[6]  A. Hassanien,et al.  Impact of Charge Transfer Complex on the Dielectric Relaxation Processes in Poly(methyl methacrylate) Polymer , 2022, Molecules.

[7]  A. Hassanien,et al.  Impedance spectroscopy and DFT/TD-DFT studies of diyttrium trioxide for optoelectronic fields , 2022, Journal of Rare Earths.

[8]  Guishan Liu,et al.  Detection of early bruises in jujubes based on reflectance, absorbance and Kubelka-Munk spectral data , 2022, Postharvest Biology and Technology.

[9]  R. El-Mallawany,et al.  Impact of Yb2O3 on the physical, bonding, dispersion and dielectric properties of Li2O–ZnO–P2O5 glasses , 2022, Materials Science in Semiconductor Processing.

[10]  Yunhui Huang,et al.  Boosting the cyclability of tetracyanoquinodimethane (TCNQ) as cathode material in aqueous battery with high valent cation , 2021, Energy Storage Materials.

[11]  M. Vasilevskiy,et al.  Use and misuse of the Kubelka-Munk function to obtain the band gap energy from diffuse reflectance measurements , 2021, Solid State Communications.

[12]  S. Landi.  Comment on “Photocatalytic degradation of RhB from an aqueous solution using Ag3PO4/N-TiO2 heterostructure” and “Evaluation of the effect of dose change of Fe3O4 nanoparticles on electrochemical biosensor compatibility using hydrogels as an experimental living organism model” , 2021 .

[13]  M. Khaleeq-ur-Rahman,et al.  Microstructural and Optical study of polycrystalline manganese oxide films using Kubelka-Munk function , 2021, Thin Solid Films.

[14]  M. El-Nahass,et al.  Optical spectroscopic studies on poly(methyl methacrylate) doped by charge transfer complex , 2021, Optical Materials.

[15]  M. Refat,et al.  Charge-transfer (CT) dynamics of triamterene with 2,3-dichloro-5,6-dicyano-p-benzoquinone acceptor: A n → π* model CT complex generated by liquid- and solid-state reactions , 2021, Journal of Molecular Liquids.

[16]  A. Hassanien.  Surface topology, optical spectroscopic and electrical studies on boron subphthalocyanine chloride thin films , 2021, Journal of Dispersion Science and Technology.

[17]  W. Qin,et al.  Light-driven molecular motion modifying the electronic structure and spin properties of solid organic superstructure , 2021 .

[18]  M. Refat,et al.  Charge-transfer chemistry of azithromycin, the antibiotic used worldwide to treat the coronavirus disease (COVID-19). Part III: A green protocol for facile synthesis of complexes with TCNQ, DDQ, and TFQ acceptors , 2021, Journal of Molecular Liquids.

[19]  Jinxin Gao,et al.  A fluorescein sodium wide-area pH optical sensor based on amplification characteristics , 2021 .

[20]  Daoben Zhu,et al.  Electronic structure engineering in organic thermoelectric materials , 2021 .

[21]  M. Refat,et al.  Correlations between spectroscopic data for charge-transfer complexes of two artificial sweeteners, aspartame and neotame, generated with several π-acceptors , 2021, Journal of Molecular Liquids.

[22]  M. Refat,et al.  Exploring the charge-transfer chemistry of fluorine-containing pyrazolin-5-ones: The complexation of 1-methyl-3-trifluoromethyl-2-pyrazoline-5-one with five π-acceptors , 2021 .

[23]  K. Miyoshi,et al.  Synthesis, properties and graft polymerization of ionic conjugated polymers with TCNQ anion radical , 2021 .

[24]  A. Rubino,et al.  Admittance spectroscopy and material modeling for organic electronic applications , 2021 .

[25]  Ji-Whan Ahn,et al.  Low concentrated phosphorus sorption in aqueous medium on aragonite synthesized by carbonation of seashells: Optimization, kinetics, and mechanism study. , 2020, Journal of environmental management.

[26]  M. El-Nahass,et al.  Structural, electrochemical and optical properties of 1,2,4-triazine derivative , 2020, Applied Physics A.

[27]  M. Karthikeyan,et al.  Systematic measurements of charge transfer complexes caused from 1-phenyl-1,2,3,4-tetrahydroisoquinoline and 4-aminoacetanilide with series of π-acceptors (BQ, DDQ, TCNQ). , 2020, Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy.

[28]  R. El-Mallawany,et al.  FTIR, UV–Vis–NIR spectroscopy, and gamma rays shielding competence of novel ZnO-doped vanadium borophosphate glasses , 2020, Journal of Materials Science: Materials in Electronics.

[29]  Jiezhi Chen,et al.  Two-dimensional electronic and charge-transport properties of a monolayer organic crystal: Impacts of the collinear transfer-integral correlations , 2020 .

[30]  G. Chadeyron,et al.  Revisiting fluorescein and layered double hydroxide using a synergistic approach: A complete optical study , 2019, Journal of Luminescence.

[31]  R. Kumar,et al.  Diffuse reflectance spectroscopy: An effective tool to probe the defect states in wide band gap semiconducting materials , 2018, Materials Science in Semiconductor Processing.

[32]  Zhihui Wang,et al.  Organic dyes containing indolodithienopyrrole unit for dye-sensitized solar cells , 2018 .

[33]  Jinghan He,et al.  Electrode buffer layers producing high performance nonvolatile organic write-once-read-many-times memory devices , 2017 .

[34]  J. Iqbal,et al.  Linear and non-linear optics of nano-scale 2′,7′dichloro-fluorescein/FTO optical system: Bandgap and dielectric analysis , 2016 .

[35]  Luís M. N. B. F. Santos,et al.  Optical band gaps of organic semiconductor materials , 2016 .

[36]  D. Souri,et al.  A new method for the determination of optical band gap and the nature of optical transitions in semiconductors , 2015, Applied Physics B.

[37]  Nishant Kumar,et al.  Biogenic synthesis and photocatalytic activity of CdS nanoparticles , 2014 .

[38]  M. El-Nahass,et al.  Optical characterizations of thermally evaporated perylene-66 (dye content 40%) thin films , 2013 .

[39]  Y. Bando,et al.  One dimensional ternary Cu–Bi–S based semiconductor nanowires: synthesis, optical and electrical properties , 2012 .

[40]  M. El-Nahass,et al.  Influence of X-ray irradiation on the optical properties of iron (III) chloride tetraphenylporphyrin thin films , 2010 .

[41]  E. Suh,et al.  White light emission from a blue LED, combined with a sodium salt of fluorescein dye , 2007 .

[42]  M. Fox.  Optical Properties of Solids , 2010 .

[43]  Daniel Dupont,et al.  Bibliographical review for reflectance of diffusing media , 2001 .

[44]  N. George,et al.  Optical absorption studies of free (H2Pc) and rare earth (RePc) phthalocyanine doped borate glasses , 2000 .

[45]  A. Becke.  Density-functional thermochemistry. III. The role of exact exchange , 1993 .

[46]  P. C. Hariharan,et al.  The effect of d-functions on molecular orbital energies for hydrocarbons , 1972 .

[47]  Martin Gouterman,et al.  Study of the Effects of Substitution on the Absorption Spectra of Porphin , 1959 .