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Investigation of Solvent Effect and H-Bonding on Spectroscopic Properties of 1-(3-Amino-6-(2,5-dichlorothiophen-3-yl)-4-phenylfuro[2,3-b]Pyridin-2-yl) Ethenone: Experimental and Computational Study

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Abstract

The furo[2,3-b]pyridine moiety is an important scaffold for many biologically active compounds, therefore, the spectral data of the derivative 1-(3-Amino-6-(2,5-dichlorothiophen-3-yl)-4-phenylfuro[2,3-b]pyridin-2-yl) ethenone (FP1) were investigated. Analysis of absorption-pH profile and Förster cycle of FP1 revealed that its excited state is more acidic than its ground state (\(p{{K}_{a}}^{*}\) < \(p{K}_{a}\)). The main fluorescence emission band of FP1 at 480 nm (in hexane) is shifted to longer wavelengths with increasing polarities of solvents. Linear Lippert’s plot and linear correlation between bands maxima and Camlet-Taft parameter, α, of the protic solvents indicated efficient intramolecular charge transfer and noticeable H-bonding. Moreover, the disappearance of the absorption band of FP1 at 385 nm in water, along with the noticeable red shift and quenching of the emission band, and the lower lifetime, relative to nonaqueous solvents, indicate the interruption of the furo[2,3-b]pyridine aromatic moiety. In addition, results from the Time Dependent Density Functional Theory (TDDFT) and Molecular Mechanic (MM) calculations were in agreement with experimentally determined spectra of FP1.

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Acknowledgements

The authors gratefully acknowledge the Deanship of Scientific Research at Al Al-Bayt University for the financial support to perform this project (No. 5/2013/2014; Date 09/01/2014). All DFT calculations were conducted on the HPC facility at the Centre of Advance Material (CAM) at the University of Sharjah.

Funding

The authors gratefully acknowledge the Deanship of Scientific Research at Al Al-Bayt University for the financial support to perform this project (No. 5/2013/2014; Date 09/01/2014). All DFT calculations were conducted on the HPC facility at the Centre of Advance Material (CAM) at the University of Sharjah.

The authors have no relevant financial or non-financial interests to disclose.

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Authors and Affiliations

  1. Department of Chemistry, Al al-Bayt University, Mafraq, Jordan

    Rasha K. Abuflaha, Raed Ghanem, Khaldoun Al-Sou’od, Omar K. Almashaqbeh & Mahmoud Al-Refai

  2. Department of Chemistry, Al-Hussein Bin Talal University, Ma’an, Jordan

    Fakhri O. Yousef

  3. Department of Chemistry, Pure and Applied Chemistry Group, University of Sharjah, P.O. Box 27272, Sharjah, UAE

    Ihsan A. Shahdi

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  1. Rasha K. Abuflaha
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Contributions

Author Contributions: Raed Ghanem and Fakhri Yousef designed the experiments and controlled the whole project and wrote the manuscript. Rasha K. Abufaha, Omar K. Almashaqbeh and Mahmoud AlRefai prepared the molecules and did the experimental part. Khaldoun Al-Sou’od, Ihsan A. Shahdi did the theoretical calculations. All authors reviewed the manuscript.

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Correspondence to Raed Ghanem.

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Abuflaha, R.K., Yousef, F.O., Ghanem, R. et al. Investigation of Solvent Effect and H-Bonding on Spectroscopic Properties of 1-(3-Amino-6-(2,5-dichlorothiophen-3-yl)-4-phenylfuro[2,3-b]Pyridin-2-yl) Ethenone: Experimental and Computational Study. J Fluoresc 33, 2349–2360 (2023). https://doi.org/10.1007/s10895-023-03243-x

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