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Synthesis, characterization, and systematic structure–property investigation of a series of carbazole–thiophene derivatives

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Abstract

A series of carbazole–thiophene oligomers linked at the 3,6-positions of the carbazole fragment of 4,4′-bis(carbazol-9-yl)biphenyl (CBP) and 4,4′-bis(carbazol-9-yl)-2,2′-dimethylbiphenyl (CDBP) with systematically elongated molecular lengths were synthesized via the Suzuki–Miyaura and Ullmann coupling reactions. Their electronic properties were studied by UV-Vis, cyclic voltammetry, and theoretical calculations. The coupling of CBP and CDBP with thiophene and bi- and terthiophene residues stabilized the HOMO and LUMO energy levels. The absorption and emission spectra exhibited a gradual red shift. The compounds with oligothiophene units had greatly decreased band gaps compared with CBP and CDBP. Therefore, these units may be introduced into the backbone of π-conjugated small molecules to develop new materials with low band gaps that may have potential applications in optoelectronics.

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Authors and Affiliations

  1. Chemistry Department, Faculty of Science, University of Malaya, Lembah Pantai, Kuala Lumpur, 50603, Malaysia

    E. F. Damit, N. Nordin & A. Ariffin

  2. Physics Department, Faculty of Science, University of Malaya, Lembah Pantai, Kuala Lumpur, 50603, Malaysia

    K. Sulaiman

Authors
  1. E. F. Damit
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  2. N. Nordin
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  3. A. Ariffin
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  4. K. Sulaiman
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Correspondence to A. Ariffin.

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The text was submitted by the authors in English.

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Damit, E.F., Nordin, N., Ariffin, A. et al. Synthesis, characterization, and systematic structure–property investigation of a series of carbazole–thiophene derivatives. Russ J Gen Chem 87, 1800–1812 (2017). https://doi.org/10.1134/S1070363217080278

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  • DOI: https://doi.org/10.1134/S1070363217080278

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