双萘二甲酰亚胺的自组装有机凝胶形成及其在对苯二胺检测中的应用。

Bis-naphthalimides self-assembly organogel formation and application in detection of p-phenylenediamine.

作者信息

Cao Xinhua, Zhao Na, Gao Aiping, Lv Haiting, Jia Yuling, Wu Renmiao, Wu Yongquan

机构信息

College of Chemistry and Chemical Engineering, Institute for Conservation and Utilization of Agro-bioresources in Dabie Mountains, Xinyang Normal University, Xinyang, Henan, 464000, PR China; State Key Laboratory of Chemo/Biosensing and Chemometrics, Hunan University, Changsha 410082, PR China.

College of Chemistry and Chemical Engineering, Institute for Conservation and Utilization of Agro-bioresources in Dabie Mountains, Xinyang Normal University, Xinyang, Henan, 464000, PR China.

出版信息

Mater Sci Eng C Mater Biol Appl. 2017 Jan 1;70(Pt 1):216-222. doi: 10.1016/j.msec.2016.08.079. Epub 2016 Aug 31.

DOI:10.1016/j.msec.2016.08.079

PMID:27770884

Abstract

Two new gelators containing bis-naphthalimides group were designed and synthesized. The gelator 1b could form gels in DMF and mixed solvent of DMSO/HO (10/1, v/v). The self-assembly processes of 1b in two kinds of solvents were detailedly investigated by UV-vis, fluorescence, infrared spectroscopy, field emission scanning electron microscope (FE-SEM), X-ray diffraction and contact angle experiments. The experiment results showed the hydrogen bonding was the main force for the gel formation. The gel 1b formed in mixed solvent of DMSO/HO (10/1, v/v) possessed of the ability of distinguishing of o-phenylenediamine, m-phenylenediamine and p-phenylenediamine. At the same time, the gelator 1b could selectively and sensitively detect p-phenylenediamine in solution with the detection limit of 8.961×10ML. The detection experiment was also confirmed by DFT theoretical calculations. This research would expand the supramolecular self-assembly materials application in sensor field and offer a new detection method for organic amines.

摘要

设计并合成了两种含双萘二甲酰亚胺基团的新型凝胶因子。凝胶因子1b能在N,N-二甲基甲酰胺（DMF）以及二甲基亚砜/水（DMSO/H₂O，体积比10/1）的混合溶剂中形成凝胶。通过紫外-可见光谱、荧光光谱、红外光谱、场发射扫描电子显微镜（FE-SEM）、X射线衍射和接触角实验，详细研究了1b在这两种溶剂中的自组装过程。实验结果表明，氢键是形成凝胶的主要作用力。在DMSO/H₂O（体积比10/1）混合溶剂中形成的凝胶1b具有区分邻苯二胺、间苯二胺和对苯二胺的能力。同时，凝胶因子1b能够选择性且灵敏地检测溶液中的对苯二胺，检测限为8.961×10⁻⁶mol/L。检测实验也得到了密度泛函理论（DFT）计算的证实。该研究将拓展超分子自组装材料在传感器领域的应用，并为有机胺提供一种新的检测方法。