Precise heteroatom doping determines aqueous solubility and self-assembly behaviors for polycyclic aromatic skeletons.
Precise heteroatom doping determines aqueous solubility and self-assembly behaviors for polycyclic aromatic skeletons.
复制标题
DOI：
10.1038/s42004-022-00724-1
复制
发表时间：
2022-08-29
影响因子：
5.9
通讯作者：
Cai, Yue-Peng
中科院分区：
文献类型：
--
作者：
Li, Kang;Hu, Jia-Min;Qin, Wei-Min;Guo, Jing;Cai, Yue-Peng
开发有效的策略来改善疏水分子支架的亲水性或水溶性，对于学术研究和工业应用都具有重要意义。在这里，我们证明了逐步和精确的N/O杂原子掺杂的多环芳香族骨架可以逐渐改变这些结构从疏水性到亲水性，甚至导致优异的水溶性。汉森溶度参数（HSP）方法表明，这三个部分溶度参数与N/O掺杂种类、数量以及在分子面板上的位置密切相关。氢键溶解度参数表明，N/O掺杂分子与水之间的氢键相互作用在增强亲水性方面起着关键作用。此外，三个优化的水溶性分子经历了自组装过程，在水中形成稳定的纳米粒子，从而促进更好的氢键相互作用揭示HSP计算，NMR和单晶X-射线分析。从NMR和发光的角度来看，这些合奏甚至显示出在水中的准固体性质。增强疏水性分子支架的亲水性允许增加它们的水溶性，并因此增加它们在一系列应用中的可用性。在这里，N/O杂原子掺杂的多环芳烃显示从疏水性到亲水性的骨架切换，提高水溶性，并促进在水中的自组装。
Developing effective strategies to improve the hydrophilicity or aqueous solubility of hydrophobic molecular scaffolds is meaningful for both academic research and industrial applications. Herein, we demonstrate that stepwise and precise N/O heteroatoms doping on a polycyclic aromatic skeleton can gradually alter these structures from hydrophobic to hydrophilic, even resulting in excellent aqueous solubility. The Hansen solubility parameters (HSP) method shows that the three partial solubility parameters are closely related to N/O doping species, numbers and positions on the molecular panel. The hydrogen bonding solubility parameter indicates that the hydrogen bonding interactions between N/O doped molecules and water play a key role in enhancing hydrophilicity. Moreover, three optimized water-soluble molecules underwent a self-assembly process to form stable nanoparticles in water, thus facilitating better hydrogen bonding interactions disclosed by HSP calculations, NMR and single crystal X-ray analysis. These ensembles even show quasi-solid properties in water from NMR and luminescence perspectives. Enhancing the hydrophilicity of hydrophobic molecular scaffolds allows to increase their aqueous solubility and therefore their usability for a range of applications. Here, N/O heteroatom doping of polycyclic aromatic hydrocarbons is shown to switch the skeleton from hydrophobic to hydrophilic, enhancing aqueous solubility and facilitating self-assembly in water.
登录
查看更多内容
影响因子：
4.1
作者：
Nakano, Hideyuki;Nakamura, Daisuke
通讯作者：
Nakamura, Daisuke
影响因子：
16.6
作者：
Ensing, Bernd;Tiwari, Ambuj;Woutersen, Sander
通讯作者：
Woutersen, Sander
影响因子：
1.8
作者：
Feng, Xinliang;Pisula, Wojciech;Muellen, Klaus
通讯作者：
Muellen, Klaus
影响因子：
17.1
作者：
Bergin, Shane D.;Sun, Zhenyu;Coleman, Jonathan N.
通讯作者：
Coleman, Jonathan N.
影响因子：
15
作者：
Fennel, Franziska;Wolter, Steffen;Lochbrunner, Stefan
通讯作者：
Lochbrunner, Stefan