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Azaindolo[3,2,1‐ jk ]carbazoles: New Building Blocks for Functional Organic Materials
Author(s) -
Kader Thomas,
Stöger Berthold,
Fröhlich Johannes,
Kautny Paul
Publication year - 2019
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201805578
Subject(s) - carbazole , pyridine , intermolecular force , solid state , characterization (materials science) , hydrogen bond , ring (chemistry) , chemistry , materials science , nitrogen , combinatorial chemistry , polymer chemistry , nanotechnology , organic chemistry , molecule
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 of pyridine‐like nitrogen into the fully planar indolo[3,2,1‐ jk ]carbazole backbone. Furthermore, the nitrogen position decisively impacted intermolecular hydrogen bonding and thus the solid‐state alignment. Ultimately, the versatility of the azaindolo[3,2,1‐ jk ]carbazoles scaffold makes this class of materials an attractive new building block for the design of functional organic materials.