Che Austin, Ghaseminezhad Homayoun, Zellmann-Parrotta Carson O, Duong Jessica, Williams Vance E, Ling Chang-Chun
Department of Chemistry, University of Calgary, 2500 University Drive NW, Calgary, AB T2N 1N4, Canada.
Department of Chemistry, Simon Fraser University, Burnaby, BC V5A 1S6, Canada.
Molecules. 2024 Nov 28;29(23):5633. doi: 10.3390/molecules29235633.
This study explores the liquid crystalline properties of novel amphiphilic β-cyclodextrin derivatives functionalized with seven oligoethylene glycol chains at the primary face, terminated with either an O-methyl or an O-cyanoethyl group, and fourteen hydrophobic aliphatic chains (elaidic or oleic acids) at the secondary face. These derivatives were designed to study the impact of chain conformation and terminal group polarity on their mesomorphic behavior. Thermal, microscopic, and X-ray diffraction studies revealed that the elaidic derivatives form columnar hexagonal mesophases, with the O-cyanoethyl derivative undergoing a slow, temperature-dependent transition to a bicontinuous cubic phase. The oleic derivatives, although less stable, also exhibit columnar hexagonal phases, but clear differences were observed in the clearing temperatures between these two groups of molecules, and they are also different from analogous derivatives containing no alkene functionalities. This work provides direct insights into the structure-mesomorphic property relationships of amphiphilic cyclodextrins in terms of the geometry and conformation flexibility of the hydrophobic regions, as well as the functional group attached to the end of the polar region.
本研究探索了新型两亲性β-环糊精衍生物的液晶性质，这些衍生物在主面用七条低聚乙二醇链官能化，末端为O-甲基或O-氰乙基，在次面有十四条疏水脂肪链（反油酸或油酸）。设计这些衍生物是为了研究链构象和端基极性对其介晶行为的影响。热学、显微镜和X射线衍射研究表明，反油酸衍生物形成柱状六方中间相，O-氰乙基衍生物会缓慢地、随温度转变为双连续立方相。油酸衍生物虽然稳定性较差，但也呈现柱状六方相，不过在这两组分子的清亮点温度上观察到明显差异，并且它们也与不含烯烃官能团的类似衍生物不同。这项工作就疏水区域的几何形状和构象灵活性以及极性区域末端连接的官能团，直接深入了解了两亲性环糊精的结构-介晶性质关系。
