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Synthesis and Photophysical Properties of 3,6-Diphenyl-9-hexyl-9H-carbazole Derivatives Bearing Electron Withdrawing Groups

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Summary.

3,6-Diphenyl-9-hexyl-9H-carbazole derivatives bearing electron withdrawing groups, such as the formyl or the nitro-group in 4-positions of the phenyl substituents, were prepared and characterized. Their photophysical properties were evaluated and compared with those of the unsubstituted counterpart 3,6-diphenyl-9-hexyl-9H-carbazole. The electron withdrawing groups bearing compounds exhibited considerable red shifts of the absorption and the emission maxima. While 3,6-di(4-nitrophenyl)-9-hexyl-9H-carbazole emitted in the orange region of the visible spectrum with its emission maximum peaking at 585 nm, 3,6-di(4-formylphenyl)-9-hexyl-9H-carbazole gave a pure blue emission with a luminescence quantum yield of 95% peaking at 450 nm. Observed features were explained using quantum mechanical calculations and organic light emitting diodes using the formylphenyl substituted compound as emissive layer were built demonstrating the practical applicability of this class of compounds.

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Authors and Affiliations

  1. Institute of Chemistry and Technology of Organic Materials, Graz University of Technology, Graz, Austria

    Gabriele Kremser, Stefan Kappaun & Christian Slugovc

  2. Institute of Solid State Physics, Graz University of Technology, Graz, Austria

    Oliver T. Hofmann, Stefan Sax, Emil J. W. List & Egbert Zojer

  3. NanoTecCenter Weiz Forschungsgesellschaft mbH, Weiz, Austria

    Stefan Sax, Stefan Kappaun & Emil J. W. List

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  1. Gabriele Kremser
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  2. Oliver T. Hofmann
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  3. Stefan Sax
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  4. Stefan Kappaun
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  5. Emil J. W. List
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  6. Egbert Zojer
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  7. Christian Slugovc
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Correspondence to Christian Slugovc.

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Kremser, G., Hofmann, O., Sax, S. et al. Synthesis and Photophysical Properties of 3,6-Diphenyl-9-hexyl-9H-carbazole Derivatives Bearing Electron Withdrawing Groups. Monatsh Chem 139, 223–231 (2008). https://doi.org/10.1007/s00706-007-0774-3

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