通往氮杂芴醇核心液晶的定向和远程金属化-铃木-宫浦交叉偶联路线
Directed and Remote Metalation-Suzuki-Miyaura Cross Coupling Route to Azafluorenol Core Liquid Crystals.
作者信息
Lai Ping-Shan, Jansen-van Vuuren Ross D, Lemieux Robert P, Snieckus Victor
机构信息
Queen's University, Chernoff Hall, 9 Bader Lane, Kingston, Ontario K7K 2N1, Canada.
Department of Chemistry, University of Waterloo, 200 University Avenue W., Waterloo, Ontario N2L 3G1, Canada.
出版信息
J Org Chem. 2021 Dec 17;86(24):17543-17549. doi: 10.1021/acs.joc.1c01027. Epub 2021 Dec 1.
Two new smectic C* mesogens containing a hexyloxy side chain and an azafluorenone () or azafluorenol () core were synthesized using a combined directed metalation-directed remote metalation-Suzuki-Miyaura cross-coupling strategy. was formed in 10 steps and 25% overall yield based on starting benzamide . forms a nematic phase, while forms a smectic A phase. The large temperature range of the smectic phase for the azafluorenol is indicative of mesophase stabilization by intermolecular hydrogen bonding between the hydroxyl group and pyridine nitrogen of neighboring molecules.
采用定向金属化-远程金属化-铃木-宫浦交叉偶联相结合的策略，合成了两种新的含有己氧基侧链和氮杂芴酮（）或氮杂芴醇（）核心的近晶C*液晶基元。基于起始苯甲酰胺，经10步反应合成得到，总产率为25%。形成向列相，而形成近晶A相。氮杂芴醇的近晶相温度范围较大，表明相邻分子的羟基与吡啶氮之间通过分子间氢键实现了中间相稳定。
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