Buchwald–Hartwig Amination of Aryl Halides with Heterocyclic Amines in the Synthesis of Highly Fluorescent Benzodifuran-Based Star-Shaped Organic Semiconductors

Autor:	Dariusz Kędziera, Alicja A Zielińska, Mariusz J. Bosiak, Piotr Trzaska, Jörg Adams
Jazyk:	angličtina
Rok vydání:	2021
Předmět:	chemistry.chemical_compound chemistry Carbazole Phenothiazine Aryl Organic Chemistry Polymer chemistry Solvatochromism Diphenylamine Buchwald–Hartwig amination Phenoxazine Amination Article
Zdroj:	The Journal of Organic Chemistry
ISSN:	1520-6904 0022-3263
Popis:	The study of palladium-catalyzed amination of bromobenzene with aromatic and heterocyclic amines, widely used in the synthesis of organic semiconductors, was performed. The best conditions for the coupling of aryl bromides with carbazole, diphenylamine, phenoxazine, phenothiazine, 9,9-dimethyl-9,10-dihydroacridine, and their derivatives have been developed. Based on the results, nine new star-shaped organic semiconductors, exhibiting up to 100% fluorescent quantum yield in the 400-550 nm range, have been synthesized in good yields. The TDDFT calculations of the absorption spectra revealed a good correlation with experimental results and slight solvatochromic effects with a change in the polarity of the solvent.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::9df42b7327bd33600ec65d67ef1a6db5 http://europepmc.org/articles/PMC8689646 Zobrazit plný text záznamu