Citation: 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. doi: 10.6023/A19060214 shu

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

Corresponding author: Zhao Xin, xzhao@sioc.ac.cn Li Zhan-Ting, ztli@fudan.edu.cn
Received Date: 15 June 2019
Available Online: 28 August 2019
Fund Project: Project supported by the National Natural Science Foundation of China (Nos. 21432004, 21890732)the National Natural Science Foundation of China 21890732the National Natural Science Foundation of China 21432004

Figures(8)

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.
- supramolecular organic framework,
- fluorescence sensing,
- 2, 4, 6-trinitrophenol,
- cucurbituril,
- self-assembly
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