Synthesis and Photophysical Properties of 3,6-Diphenyl-9-hexyl-9H-carbazole Derivatives Bearing Electron Withdrawing Groups |
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Authors: | Gabriele Kremser Oliver T Hofmann Stefan Sax Stefan Kappaun Emil J W List Egbert Zojer and Christian Slugovc |
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Institution: | (1) Departamento de Química, Universidade de Coimbra, 3004-535 Coimbra, Portugal;(2) INETI-DTIQ, Estrada do Paço do Lumiar, 22, 1649-038 Lisbon, Portugal |
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Abstract: | 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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