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  • Title: Synthesis and properties of methoxyphenyl-substituted derivatives of indolo[3,2-b]carbazole.
    Author: Simokaitiene J, Stanislovaityte E, Grazulevicius JV, Jankauskas V, Gu R, Dehaen W, Hung YC, Hsu CP.
    Journal: J Org Chem; 2012 Jun 01; 77(11):4924-31. PubMed ID: 22537513.
    Abstract:
    The synthesis and full characterization of new derivatives of indolo[3,2-b]carbazole with differently substituted phenyl groups at nitrogen atoms is reported. Comparative study on their thermal, optical electrochemical, and photoelectrical properties is presented. The synthesized compounds are electrochemically stable. Their highest occupied molecular orbital energy values range from -5.14 to -5.07 eV. The electron photoemission spectra of the films of synthesized materials revealed the ionization potentials of 5.31-5.47 eV. Hole drift mobility of the amorphous film of 5,11-bis(3-methoxyphenyl)-6-pentyl-5,11-dihydroindolo[3,2-b]carbazole exceed 10(-3) cm(2)/V·s at high electric fields, as it was established by xerographic time-of-flight technique. In contrast to diphenylamino substituted derivatives of carbazole, no effect of the position of methoxy groups on the photoelectrical properties was observed for the synthesized methoxyphenyl-substituted derivatives of indolo[3,2-b]carbazole. The indolo[3,2-b]carbazole core has a larger resonance structure that includes 3 phenyl rings, and thus the energy gap of the HOMO and LUMO π orbitals is lower as compared to that of carbazoles. With a larger energy difference between the phenyl substituents and the core moiety, the indolo[3,2-b]carbazole derivatives studied all have a weaker coupling between the phenyl group and a much weaker dependence of the molecular properties on the position of substituents on the phenyl groups as compared to those observed in substituted carbazoles.
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