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Novel type of azomethine with combined effects of thiophene cores and vicinal cyano groups

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Abstract

Through the condensation of 2,5-diaminothiophene-3,4-dicarbonitrile with thiophene-2-carbaldehyde, a new homologue of azomethine-based compounds was achieved. The newly synthesized 2,5-bis-[(thiophen-2-ylmethylene)amino]thiophene-3,4-dicarbonitrile consists of three thiophene cores showing structural similarity to terthiophene, which is commonly employed as a part of the active layers in organic semiconductors. Additionally, the imine linkage (–HC = N–) affects the planar arrangement of the compound, enhancing the effective π-conjugation. As a result, the proximity of FMO (frontier molecular orbitals) of value 3.60 eV between the highest occupied and lowest unoccupied molecular orbital according to the DFT approach (Gamess, B3LYP/6-31g(d,p)), is achieved within the strategy of synthesis of small molecule-based organic semiconductors. The vicinal cyano groups at the Cβ-position of the central thiophene core offer the possibilities of further cyclization towards phthalocyanines and subphthalocyanines.

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Acknowledgements

Financial supports from the Slovak Ministry of Education, Science, Research and Sport under the contract no. VEGA 2/0055/21 and the Slovak Research and Development Agency APVV-17-0513 is gratefully acknowledged. The work was also financially supported by a grant of University of SS Cyril and Methodius with the project number UCM FPPV 22-2022.

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Natural Sciences, University of St. Cyril and Methodius, Trnava, Slovakia

    Marcela Gašparová, Natália Kabaňová & Zita Tokárová

  2. Center for Computational Material Science, Institute of Physics, Slovak Academy of Sciences, Bratislava, Slovakia

    Kamil Tokár

  3. Advanced Technologies Research Institute ATRI, Faculty of Materials Science and Technology in Trnava, Slovak University of Technology, Trnava, Slovakia

    Kamil Tokár

  4. Institute of Organic Chemistry, Catalysis and Petrochemistry, Faculty of Chemical and Food Technology, Slovak University of Technology, Bratislava, Slovakia

    Daniel Végh

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  1. Marcela Gašparová
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  2. Natália Kabaňová
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  3. Kamil Tokár
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  4. Daniel Végh
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  5. Zita Tokárová
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Correspondence to Marcela Gašparová.

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Gašparová, M., Kabaňová, N., Tokár, K. et al. Novel type of azomethine with combined effects of thiophene cores and vicinal cyano groups. Monatsh Chem 153, 1099–1105 (2022). https://doi.org/10.1007/s00706-022-02993-x

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