title: Synthesis, functionalization, and optical properties of chiral carbazole-based diaza[6]helicenes.
abstract: In the present study, carbazole-based diaza[6]helicenes were synthesized utilizing versatile quinoline and 9-(2-ethylhexyl)-2,7-dimethoxycarbazole-3-carbaldehyde building blocks via the Wittig reaction-photocyclization strategy. The presence of bifunctional units comprising electrophilic chloroquinoline and electron-rich carbazole has opened up new opportunities. The chloro group was substituted with a chiral amine, allowing diastereomeric separation, and the chiral forms were monofunctionalized via electrophilic substitution on the carbazole unit. Postcyclization functionalization via substituting the carbazole unit provides a platform for the synthesis of chiral functionalized materials with potential application in fields such as asymmetric synthesis and organic electronics. The configuration of the diaza[6]helicene diastereomers was demonstrated by time-dependent density functional theory (TD-DFT) calculations. Furthermore, on the basis of the DFT calculations of the HOMO-LUMO energy levels of the chiral forms, these compounds can be potentially of interest as hole-transporting compounds.
authors: Molecular Design and Synthesis, Department of Chemistry, KU Leuven , Celestijnenlaan 200F, B-3001 Leuven, Belgium.
authors: Audrius
authors: A
authors: Bucinskas
authors: Deepali
authors: D
authors: Waghray
authors: Gintautas
authors: G
authors: Bagdziunas
authors: Joice
authors: J
authors: Thomas
authors: Juozas Vidas
authors: JV
authors: Grazulevicius
authors: Wim
authors: W
authors: Dehaen