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Antiradical Properties of trans-2-(4-substituted-styryl)-thiophene

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Abstract

2-substituted thiophene compounds with electron donating and electron withdrawing p-phenyl substitution were synthesized and studied their radical scavenging properties using DPPH assay and DFT method. It is shown that p-hydroxy and p-amino phenyl substituted compound exhibit radical scavenging activity. From DFT and radical scavenging studies, a correlation between IC50 with the bond dissociation enthalpy, proton affinity, ground state dipole moment and optical band gap of compound is found. Compounds 1–3 with electron withdrawing substituent (NO2, CN, Cl) do not show any radical scavenging properties, whereas compounds 6–7 with electron donating substituent (OH, NH2) show antiradical properties. Further, the antiradical activity is reduced drastically by replacing the -OH and -NH2 with methoxy and -N-alkylating group respectively in 6 and 7. The compound with p-hydroxy phenyl substitution, exhibits stronger antiradical activity as compared to the p-amino phenyl substitution due to smaller O-H bond dissociation energy as compared to the N-H bond. From DPPH and DFT studies, it is suggested that the radical scavenging activity in 2-substituted thiophene is occurred through proton transfer mechanism. The other possible SET, SPLET mechanisms are also corroborated.

Antiradical properties of trans-2-(4-substituted-styryl)-thiophene Anamika Gusain, Naresh Kumar, Jagdeep Kumar, Gunjan Pandey, Prasanta Kumar Hota*

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Acknowledgements

PKH, AG, NK and JK are grateful to University Grants Commission, New Delhi for research grant (No F.30-72/2014-BSR) and research fellowship. GP is the recipient of national postdoctoral research fellowship from Department of Science & Technology (DST), New Delhi. Authors acknowledged AMRC, IIT Mandi for 1H NMR and 13C NMR facility.

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  1. Anamika Gusain and Naresh Kumar contributed equally to this work.

Authors and Affiliations

  1. Department of Chemistry, School of Sciences, Hemvati Nandan Bahuguna Garhwal University, Srinagar (Garhwal), Uttarakhand, 246174, India

    Anamika Gusain, Naresh Kumar, Jagdeep Kumar, Gunjan Pandey & Prasanta Kumar Hota

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  1. Anamika Gusain
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  2. Naresh Kumar
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  3. Jagdeep Kumar
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  4. Gunjan Pandey
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  5. Prasanta Kumar Hota
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Contributions

PKH, AG, NK synthesized and characterized the compounds using 1H and 13C NMR, GC-MS, FTIR techniques. PKH, AG, NK carried out the absorption, fluorescence measurement and analyzed the data. PKH, AG, NK and GP measured the antiradical activity. PKH and JK designed and JK carried out the DFT calculation. PKH, AG and NK wrote the paper.

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Correspondence to Prasanta Kumar Hota.

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Highlights

Thiophene compounds with p-hydroxy and p-amino phenyl substitutent, exhibit antiradical activity with IC50 range from 45 μM to 165μM . The activity is comparable to vitamin E (IC50 : 26 μM)

Correlation between the anti-radical activity with the ground state dipole moment, bond dissociation enthalpy, ionization potential and proton affinity of thiophene compound is elucidated.

In thiophene compounds, the radical scavenging activity is predominantly occurred through hydrogen atom transfer mechanism. The other possible mechanisms such as SET, SPLET are also discussed.

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Gusain, A., Kumar, N., Kumar, J. et al. Antiradical Properties of trans-2-(4-substituted-styryl)-thiophene. J Fluoresc 31, 51–61 (2021). https://doi.org/10.1007/s10895-020-02629-5

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