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Thienopyrrolo[3,2,1-jk]carbazoles: Building Blocks for Functional Organic Materials.

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.

SUBMITTER: Bader D

PROVIDER: S-EPMC7173703 | biostudies-literature | 2020 Mar

REPOSITORIES: biostudies-literature

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Thienopyrrolo[3,2,1-jk]carbazoles: Building Blocks for Functional Organic Materials.

Bader Dorian D Fröhlich Johannes J Kautny Paul P

The Journal of organic chemistry 20200203 5

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[ ...[more]

PMID: 31859503

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