Accelerating the thermal fading rate of photochromic naphthopyrans by pillar[5]arene-based conjugated macrocycle polymer

Liu, Shuangyan; Yan, Taishan; Wu, Qiuxia; Xu, Zheng; Han, Jie

doi:10.1016/j.cclet.2021.07.023

Cited by 14 publications

(4 citation statements)

References 42 publications

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“…As a marvelous host molecule, pillar[n]arene has been used widely as part of various water-soluble supramolecular materials in diverse practical fields such as supramolecular gelation systems [ 19 , 20 , 21 , 22 ], catalysis [ 23 , 24 , 25 ] and optical materials [ 26 , 27 , 28 , 29 ], as well as adsorption and separation materials [ 30 , 31 ]. Particularly, pillar[n]arene-based amphiphilic supramolecular polymers not only show improved water solubility but also exhibit good performance in terms of the delivery of dyes to cells for bioimaging [ 32 , 33 ].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Optical Properties and Cellular Toxicity of Water-Soluble near Infrared-II Fluorescent Assemblies Based on Pillar[5]arene

Wu,

Sun,

Yang

et al. 2023

Polymers

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The main challenges in second near-infrared region molecular fluorophores are poor water solubility and unknown long-term toxicity at present. Herein, new NIR-II molecular fluorophores have been designed and employed to integrate biocompatible pillar[5]arene with 10 outer triethylene oxide groups for the synthesis of rotaxane IRCR. In addition, PEGylated pillar[5]arenes have been combined for the self-assembly of two supramolecular vesicular systems, i.e., PP5-IR1 and PP5-IR2, affording aqueous solubility and lowered cellular toxicity. In aqueous solution, all these fluorophores displayed room-temperature emission with λmax at 986–1013 nm and quantum yields of 0.54–1.45%. They also exhibited good chemical stability and reasonable self-assembled sizes, which may find potential applications in NIR-II imaging. In addition, PP5-IR1 can be used as a fluorescent chemosensor for selective recognition of glutathione through the cleavage of dinitrophenyl ether and release the fluorescent dye.

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Section: Introductionmentioning

confidence: 99%

Synthesis, Optical Properties and Cellular Toxicity of Water-Soluble near Infrared-II Fluorescent Assemblies Based on Pillar[5]arene

Wu,

Sun,

Yang

et al. 2023

Polymers

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“…Their size-specific electron-rich hydrophobic cavities can selectively bind certain molecules through host–guest interactions [ 26 , 27 , 28 ]. The host–guest properties of macrocycles have been extensively applied in the fields of drug delivery [ 29 , 30 , 31 ], water purification [ 32 ], self-assembly [ 33 ], photochromism [ 34 , 35 ], and substance detection [ 36 , 37 , 38 , 39 ]. In particular, the development of pillararene-based macrocyclic arenes has increased rapidly since they were first reported on in 2008, and a variety of expanded versions of macrocyclic arenes, such as leaning pillar[6]arene [ 40 ], biphenyl-extended pillar[6]arene [ 41 ], geminiarenes [ 42 ], leggero pillar[5]arene [ 43 ], and hybrid [n] arenes [ 44 ], have been synthesized.…”

Section: Introductionmentioning

confidence: 99%

Separation of Low-Molecular-Weight Organics by Water-Soluble Macrocyclic Arenes

Wang

Song

et al. 2022

Molecules

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In this study, we fabricate a series of water-soluble anionic macrocyclic arenes, including pillar[5]arene (WP5), pillar[6]arene (WP6), leaning pillar[6]arene (WLT6), and biphenyl-extended pillar[6]arene (WBpP6), which show different separation capabilities toward low-molecular-weight organics, such as short chain haloalkanes, cyclic aliphatics, and aromatics, in water. The liquid–liquid distribution experiments are carried out at room temperature. The separation factor for low-molecular-weight organics is evaluated in the extraction of equimolar mixtures. WP6 demonstrates a high extraction efficiency of up to 89% in separating toluene/methylcyclohexane mixtures. These adsorbents also have the advantages of rapid adsorption, high separation efficiency, remarkable selectivity, and good recyclability. This work not only expands the application scope of macrocyclic chemistry, but also has practical research value for organics separation and water purification.

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“…To date, the relationship between the molecular structures of naphthopyrans and the photochromic properties has been investigated continuously. 33,34 However, the discolourization mechanisms, especially the effect of the additional fused cyclic units at the 2H-naphthopyran skeleton on the thermal fading rate, have been hardly explored. This has become a bottleneck problem that restricts the development of such kinds of photo-functional materials.…”

Section: Introductionmentioning

confidence: 99%

Development of photochromic fused 2H-naphthopyrans with promising thermal fading rates

Han

Yan

et al. 2022

J. Mater. Chem. C

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Accelerating the thermal fading rate of photochromic naphthopyrans by pillar[5]arene-based conjugated macrocycle polymer

Cited by 14 publications

References 42 publications

Synthesis, Optical Properties and Cellular Toxicity of Water-Soluble near Infrared-II Fluorescent Assemblies Based on Pillar[5]arene

Synthesis, Optical Properties and Cellular Toxicity of Water-Soluble near Infrared-II Fluorescent Assemblies Based on Pillar[5]arene

Separation of Low-Molecular-Weight Organics by Water-Soluble Macrocyclic Arenes

Development of photochromic fused 2H-naphthopyrans with promising thermal fading rates

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