Citation: Baoqi Wu, Rongzhi Tang, Zhi-Wei Li, Feng Lin, Zongyu Sun, Huanyu Xia, Lin Jiang, Yu Tan. Selective encapsulation of azo compounds by tetracationic cyclophane in water and photo-controlled reversible release[J]. Chinese Chemical Letters, ;2025, 36(9): 110896. doi: 10.1016/j.cclet.2025.110896 shu

Selective encapsulation of azo compounds by tetracationic cyclophane in water and photo-controlled reversible release

Baoqi Wu ^{a, 1} ,
Rongzhi Tang ^{b, 1} ,
Zhi-Wei Li ^c ,
Feng Lin ^a ,
Zongyu Sun ^a ,
Huanyu Xia ^a ,
Lin Jiang ^a ,
Yu Tan ^{a, *,}

a.
School of Chemical Engineering and Technology, Sun Yat-sen University, Zhuhai 519082, China
b.
School of Energy and Environment, City University of Hong Kong, Hong Kong 999077, China
c.
School of Chemistry, Sun Yat-sen University, Guangzhou 510006, China

tany78@mail.sysu.edu.cn

Received Date: 1 October 2024
Revised Date: 4 January 2025
Accepted Date: 20 January 2025
Available Online: 31 January 2025

Figures(6)

Many azo compounds and their intermediates are toxic and have been linked to various health issues, representing a growing global problem. Molecular engineering for selective encapsulation of azobenzene compounds is critical, given their significant use in smart materials and prevalence as environmental micropollutants released from the food and dye industries. However, the current host molecules catering to azobenzene compounds are mainly limited to cyclodextrins, pillar[n]arenes and cucurbit[n]urils, demonstrating a moderate affinity. This report describes that a novel 3,3′-bipyridinium-based cyclophane was capable of encapsulating anionic azobenzene compounds in water with high binding affinity and pH stability through electrostatic attraction-enhanced mechanism, surpassing the extensively reported supramolecular systems. 1D & 2D NMR experiments, UV–vis spectrum, X-ray crystallography and computational modeling were carried out to understand the host-guest complexation. It's worth noting that the tetracationic cyclophane exhibited good selective and anti-interference encapsulation properties in binary, ternary and seawater systems. Furthermore, upon UV/white light irradiation, the reversible conversion between (E)-4,4′-azobisbenzoate and (Z)-4,4′-azobisbenzoate triggers the dissociation/recomplexation of the host-guest complex within 3 min. This reversible photo-switchable (E)-disodium 4,4′-azobisbenzoate-BPy-Box⁴⁺ supramolecular system holds promise for designing novel materials for extraction/release of azo compounds and other small smart materials.
- Cyclophane,
- Macrocycle,
- Molecular recognition,
- Photo-switchable,
- Encapsulation
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