Synthesis and self-assembly of novel oxacalix[2]arene[2]triazine amphiphiles

• Published in: Science China. Chemistry Vol. 59; no. 10; pp. 1306 - 1310
• Main Authors: Xu, Ruibin, Hou, Baoyong, Wang, Dexian, Wang, Meixiang
• Format: Journal Article
• Language: English
• Published: Beijing Science China Press 01.10.2016; Springer Nature B.V
• Subjects: Chemistry; Chemistry and Materials Science; Chemistry/Food Science; Hydrogen bonds; Photon correlation spectroscopy; Self-assembly; Tetrahydrofuran; 三嗪; 分子自组装; 动态光散射; 合成; 大环分子; 杯芳烃; 自组装行为; 超分子化学; self-assembly; oxacalixarenetriazine; heteracalixaromatics; amphiphile
• ISSN: 1674-7291; 1869-1870
• DOI: 10.1007/s11426-016-0169-3

Heteracalixaromatics are an emerging generation of macrocyclic host molecules in supramolecular chemistry. As a typical example of heteracalixaromatics, oxacalix[2]arene[2]triazine adopts a shape-persistent 1,3-alternate conformation and can be easily functionalized. Taking it as a platform, a series of oxacalix[2]arene[2]triazine-based amphiphiles bearing long alkyl chains were synthesized through post-macrocyclization functionalization or 3＋1 fragment coupling protocols. The self-assembly behavior of these arnphiphiles in a mixture of tetrahydrofuran （THF） and water was investigated. Dynamic light scattering （DLS） measurements revealed that the size of the self-assembled aggregates is dependent on the structure of the amphiphiles. The long alkyl chain substituents and/or interrnolecular hydrogen bonds were found to promote the self-assembly.