Abstract
The facile preparation of three regioisomeric thienopyrrolo[3,2,1-jk]carbazoles applying a convenient C–H activation approach is presented. The incorporation of thiophene into the triarylamine framework significantly impacted the molecular properties in comparison to the analogous indolo[3,2,1-jk]carbazole scaffold. Dependent on the exact substitution pattern, the absorption onsets of the new materials are shifted toward slightly higher wavelengths compared to the analogous indolo[3,2,1-jk]carbazole, whereas the emission maxima of the sulfur derivatives is shifted from 375 to 410 nm. In analogy, the HOMO–LUMO energy gap of the thienopyrrolo[3,2,1-jk]carbazoles is reduced compared to indolo[3,2,1-jk]carbazole. Therefore, the developed thienopyrrolo[3,2,1-jk]carbazoles enrich the family of triarylamine donors and constitute a novel building block for functional organic materials.
Highlights
The facile preparation of three regioisomeric thienopyrrolo[3,2,1-jk]carbazoles applying a convenient C−H activation approach is presented
The versatility of the ICz building block has been demonstrated by its application as a donor in push−pull photosensitizers for dye-sensitized solar cells.[25−27] ICz has been employed as weak electron acceptor in thermally activated delayed fluorescent (TADF) emitters.[28,29]
We developed a series of nitrogen substituted ICz derivatives (NICz, Scheme 1) and tuned the energy levels of the highest occupied molecular orbitals (HOMOs) and lowest unoccupied molecular orbitals (LUMOs) over a wide range.[21]
Summary
The facile preparation of three regioisomeric thienopyrrolo[3,2,1-jk]carbazoles applying a convenient C−H activation approach is presented. Regarding the HOMO−LUMO energy gaps, thiophene incorporation has similar effects on the thienopyrrolo[3,2,1jk]carbazoles.
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