Synthesis, Functionalization, and Optical Properties of Chiral Carbazole-Based Diaza[6]helicenes

Autor:	Gintautas Bagdziunas, Audrius Bucinskas, Wim Dehaen, Deepali Waghray, Juozas V. Grazulevicius, Joice Thomas
Rok vydání:	2015
Předmět:	Electrophilic substitution chemistry.chemical_compound chemistry Helicene Carbazole Organic Chemistry Wittig reaction Quinoline Enantioselective synthesis Diastereomer Organic chemistry Bifunctional Combinatorial chemistry
Zdroj:	The Journal of Organic Chemistry. 80:2521-2528
ISSN:	1520-6904 0022-3263
DOI:	10.1021/jo5024188
Popis:	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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::283c442d24470304c4bc0d86810d54c6 https://doi.org/10.1021/jo5024188 Zobrazit plný text záznamu