2019
DOI: 10.1002/chem.201805578
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Azaindolo[3,2,1‐jk]carbazoles: New Building Blocks for Functional Organic Materials

Abstract: The preparation and characterization of 12 azaindolo[3,2,1‐ jk ]carbazoles is presented. Ring‐closing C−H activation allowed for the convenient preparation of six singly and six doubly nitrogen‐substituted indolo[3,2,1‐ jk ]carbazole derivatives in which ten of the materials have not been described in the literature before. The detailed photophysical and electrochemical characterization of the developed materials revealed a significant impact of the incorporation o… Show more

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Cited by 19 publications
(23 citation statements)
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“…The molecules under investigation were synthesized by ring closure of 9-(2-bromophenyl)-9H-carbazole derivatives with the appropriate N-substitution patterns using 5 mol% of an allyl[1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene]chloropalladium(II) catalyst. Reaction optimization studies and full characterizations are given by Kader et al (2019). Crystals were grown by slow evaporation of acetonitrile solutions.…”
Section: Synthesis and Crystal Growthmentioning
confidence: 99%
“…The molecules under investigation were synthesized by ring closure of 9-(2-bromophenyl)-9H-carbazole derivatives with the appropriate N-substitution patterns using 5 mol% of an allyl[1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene]chloropalladium(II) catalyst. Reaction optimization studies and full characterizations are given by Kader et al (2019). Crystals were grown by slow evaporation of acetonitrile solutions.…”
Section: Synthesis and Crystal Growthmentioning
confidence: 99%
“…[17][18][19] A convenient synthetic approach towards ICz based on C-H activation renders the widespread application of this particular moiety possible. 17,20,21 ICz can be considered a fully planarized derivative of triphenylamine (TPA) and phenylcarbazole (PCz)triarylamine building blocks which are widely employed as electron donors. 22 However, stepwise planarization of TPA decreases the electron donating properties of the triarylamine as the lone pair of the central nitrogen is incorporated into the aromatic system of one (PCz) or two (ICz) pyrrole rings (Scheme 1) and induces light electron accepting properties.…”
mentioning
confidence: 99%
“…29 Therefore, we developed a series of nitrogen substituted ICz derivatives (NICz, Scheme 1) and were able to tune the energy levels of the highest occupied molecular orbitals (HOMOs) and lowest unoccupied molecular orbitals (LUMOs) over a wide range. 21 Inspired by these results we set out, to reverse the effect of increased electron deficiency by incorporation of sulfur atoms into the ICz scaffold. Substitution of one benzene ring by thiophene should increase the electron donating power and the HOMO level of the annulated system, yet retaining planarity, which is an important feature for intermolecular interactions and the overall alignment and thus interaction of individual molecules in the solid state.…”
mentioning
confidence: 99%
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