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亚环性库库比特[n]uril 含有硫酸离子组的硫酸
Christian Akakpo1, Peter Y Zavalij1, Lyle Isaacs1
1Department of Chemistry and Biochemistry, University of Maryland, College Park, Maryland 20742, United States.
Beilstein journal of organic chemistry
|April 8, 2025
概括
一个新的非循环库库尔比图里尔宿主,C1,与硫酸基团显示较低的水溶性和自我结合比M1. C1对氨客体,特别是四级客体具有增强的结合.
科学领域:
- 超分子化学 超分子化学
- 主机和客人的化学反应
- 有机合成 有机合成
背景情况:
- 循环子[n]urils (CB[n]) 是具有可调节性质的宏循环宿主.
- 离子功能组显著影响CB[n]的溶解性和结合性.
- 了解结构-属性关系是设计新型CB[n]主机的关键.
研究的目的:
- 合成和表征一种新型的非循环甲基[n]uril宿主 (C1),具有四个硫酸离子组.
- 调查硫酸盐组对C1的溶解性,自我关联性和分子识别性能的影响.
- 为了比较C1与相关的硫酸盐功能化宿主 (M1) 的结合亲和力,用于客.
主要方法:
- 合成和特征的非循环黄[n]uril主体C1.1.
- 进行X射线晶体学以确定C1·Me-CHDA复合物的结构.
- 1H NMR光谱和稀释实验,以评估可溶性和自我关联.
- 1H NMR光谱和异热定位热量计 (ITC) 来评估宿主-客体结合.
主要成果:
- 顺利合成和特征化了非循环的甲[n]uril宿主C1.
- 确定了C1·Me-CHDA复合物的X射线晶体结构.
- 与M1 (346 mM) 相比,C1的水溶性 (4 mM) 显著降低,自我关联率最低.
- C1对客体的结合亲和力略强于M1,偏好四级离子.
结论:
- 酸硫酸盐组存在于非循环曲[n]urils中,影响其物理化学特性,特别是降低水溶性.
- 与其硫酸盐模拟物M1.1相比,环状库库比图里尔宿主C1显示出明显的分子识别行为.
- C1显示出作为特定客的宿主分子的潜力,特别是四级离子.
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