Self-Assembly of a Highly Fluorescent Three-Dimensional Supramolecular Organic Framework and Selective Sensing for Picric Acid

doi:10.6023/A19060214

Acta Chimica Sinica ›› 2019, Vol. 77 ›› Issue (8): 735-740.DOI: 10.6023/A19060214 Previous Articles Next Articles

Special Issue: 分子探针、纳米生物学与生命分析化学

Article

一个强荧光三维超分子有机框架的构建及其对苦味酸的选择性传感

吴义鹏^a, 王泽坤^a, 王辉^a, 张丹维^a, 赵新^b, 黎占亭^a

a 复旦大学化学系上海市分子催化与功能材料重点实验室上海 200438;
b 中国科学院上海有机化学研究所有机功能分子合成与组装化学重点实验室上海 200032

投稿日期:2019-06-15 发布日期:2019-06-28
通讯作者: 赵新, 黎占亭 E-mail:xzhao@sioc.ac.cn;ztli@fudan.edu.cn
基金资助:
项目受国家自然科学基金（Nos.21432004，21890732）资助.

Self-Assembly of a Highly Fluorescent Three-Dimensional Supramolecular Organic Framework and Selective Sensing for Picric Acid

Wu Yi-Peng^a, Wang Ze-Kun^a, Wang Hui^a, Zhang Dan-Wei^a, Zhao Xin^b, Li Zhan-Ting^a

a Department of Chemistry, Shanghai Key Laboratory of Molecular Catalysis and Innovative Materials, Fudan University, Shanghai 200438, China;
b Key Laboratory of Synthetic and Self-Assembly Chemistry for Organic Functional Molecules, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China

Received:2019-06-15 Published:2019-06-28
Contact: 10.6023/A19060214 E-mail:xzhao@sioc.ac.cn;ztli@fudan.edu.cn
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21432004, 21890732).

1. Self-Assembly of a Highly Fluorescent Three-Dimensional Supramolecular Organic Framework and Selective Sensing for Picric Acid.PDF(734KB)

Abstract

Cucurbit[8]uril (CB[8])-encapsulation-based host-guest chemistry has been utilized to construct supramolecular organic frameworks, a family of water-soluble, self-assembled periodic porous structures, from multi-armed preorganized building blocks. The tetrahedral prototype building block has been incorporated with four CH₂ units to connect the central tetraphenylmethane and appended aromatic arms. Herein we designed and prepared a new fully conjugated tetrahedral building block T-1, which possesses four N-methyl 4-(4-styrylphenyl)pyridinium (SPP) arms. The 1:2 mixture of T-1 with CB[8] in water leads to the formation of a new three-dimensional homogeneous diamondoid supramolecular organic framework SOF-r-SPP through CB[8] encapsulation for intermolecular dimers of the appended SPP units. ¹H NMR, absorption and fluorescence experiments conformed strong binding between the two components at diluted concentrations and 1:2 binding stoichiometry. Isothermal calorimetric (ITC) experiments established that the three-component (SPP)₂ÌCB[8] complexes formed between the SPP units of T-1 and CB[8] had an apparent binding constant of 5.5×10¹³ M^-2, which was 5.5×10⁴ times as high as that of the complex of a SPP control. ITC experiments also revealed that the self-assembly of SOF-r-SPP are driven both enthalpically and entropically, but the enthalpic contribution was overwhelmingly higher. Dynamic light scattering experiments revealed that within the concentration range of 0.031 mmol/L to 1.0 mmol/L of T-1, the framework possessed a hydrodynamic diameter of 41 nm to 68 nm. Molecular modelling study indicated that the new regular framework formed an aperture of 2.3 nm. Although T-1 has nearly no fluorescence, SOF-r-SPP exhibits strong fluorescence in water probably due to the encapsulation of the SPP dimers by CB[8] that suppresses the relative rotation of the aromatic rings. Adding nitrobenzene or naphthalene derivatives to the solution of SOF-r-SPP remarkably quenched the fluorescence of the framework. Among other sixteen nitro-bearing aromatic molecules, picric acid (2,4,6-trinitrophenol) exhibited the largest quenching ability. At the low concentration of 1.0 μmol/L for T-1 of SOF-r-SPP, 0.1 μmol/L of 2,4,6-tirnitrophenol could cause 16% quenching of the fluorescence of SOF-r-SPP and 0.1 mmol/L of 2,4,6-tirnitrophenol could realize nearly complete quench (>97%). Following a reported method, the limit of detection of SOF-r-SPP for picric acid was as low as 0.024 μmol/L.

Key words: supramolecular organic framework, fluorescence sensing, 2,4,6-trinitrophenol, cucurbituril, self-assembly

Cite this article

Wu Yi-Peng, Wang Ze-Kun, Wang Hui, Zhang Dan-Wei, Zhao Xin, Li Zhan-Ting. Self-Assembly of a Highly Fluorescent Three-Dimensional Supramolecular Organic Framework and Selective Sensing for Picric Acid[J]. Acta Chimica Sinica, 2019, 77(8): 735-740.

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一个强荧光三维超分子有机框架的构建及其对苦味酸的选择性传感

Self-Assembly of a Highly Fluorescent Three-Dimensional Supramolecular Organic Framework and Selective Sensing for Picric Acid

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