An experimental and quantum mechanical study on electrochemical properties of N-substituted pyrroles

Nurcan S. Tuzun*, Fatma Bayata, A. Sezai Sarac

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

12 Citations (Scopus)

Abstract

In this study, successful electropolymerization of a series of N-substituted monomers are reported for the first time at the same reaction conditions in a comparative sense. The electronic properties from quantum mechanical calculations (DFT B3LYP/6-31+G*) and electrochemical properties from the experiment are surveyed. The linear relationship between the inverse chain length and HOMO and HOMO-LUMO energy values of 1-Phenyl-1H-pyrrole allowed us to calculate the ionization energy and the band gap as 3.35 and 2.81 eV, respectively. The linear correlation between the Hammett parameters and the calculated HOMO energies with high regression coefficient has demonstrated the electronic effects of substituents to be important on redox behavior. The correlations between the experimental electrochemical data produced in this study and the calculated molecular orbital energies have shown a relationship between the reversibility of the process and the molecular orbital energy levels, which are in turn related to the nature of substitution.

Original languageEnglish
Pages (from-to)95-104
Number of pages10
JournalJournal of Molecular Structure: THEOCHEM
Volume857
Issue number1-3
DOIs
Publication statusPublished - 30 May 2008

Funding

The authors gratefully acknowledge the ITU High Performance Computing Center (Grant No.: 20202007) for the computer time provided.

FundersFunder number
ITU High Performance Computing Center20202007

    Keywords

    • B3LYP
    • DFT
    • Electropolymerization
    • N-substituted pyrrole
    • Pyrrole
    • Quantum mechanical calculations

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