Directed ortho and Remote Metalation–Suzuki–Miyaura Cross Coupling Route to Azafluorenol Core Liquid Crystals

Autor:	Ross D. Jansen-van Vuuren, Victor Snieckus, Ping-Shan Lai, Robert P. Lemieux
Rok vydání:	2021
Předmět:	010405 organic chemistry Metalation Hydrogen bond Organic Chemistry Intermolecular force Mesophase 010402 general chemistry 01 natural sciences 3. Good health 0104 chemical sciences chemistry.chemical_compound Crystallography chemistry Liquid crystal Phase (matter) Pyridine Side chain
Zdroj:	The Journal of Organic Chemistry. 86:17543-17549
ISSN:	1520-6904 0022-3263
Popis:	Two new smectic C* mesogens containing a hexyloxy side chain and an azafluorenone (3a) or azafluorenol (3b) core were synthesized using a combined directed ortho metalation-directed remote metalation-Suzuki-Miyaura cross-coupling strategy. 3b was formed in 10 steps and 25% overall yield based on starting benzamide 1a. 3a forms a nematic phase, while 3b forms a smectic A phase. The large temperature range of the smectic phase for the azafluorenol 3b is indicative of mesophase stabilization by intermolecular hydrogen bonding between the hydroxyl group and pyridine nitrogen of neighboring 3b molecules.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::7c08bb59daeb27bac7ed566874fff890 https://doi.org/10.1021/acs.joc.1c01027 Zobrazit plný text záznamu