Imine organic cages derived from tetraphenylethylene dialdehydes exhibiting aggregation-induced emission and explosives detection

Feng, Fan-Da; Peng, Yu-Xin; Zhang, Lei; Huang, Wei

doi:10.1016/j.dyepig.2021.109657

Cited by 11 publications

(12 citation statements)

References 41 publications

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“…Semicage , by contrast, has a slightly weaker detection sensitivity (3.15 × 10 6 M –1 , Figure S16c,d), which is still significantly higher than that of TPP (2.94 × 10 3 M –1 , Figure S16e,f). The experimental results indicated that the sensing capability of Imi-cage and Semicage for PA is significantly higher than most other previously reported hosts. , …”

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confidence: 55%

“…The experimental results indicated that the sensing capability of Imi-cage and Semicage for PA is significantly higher than most other previously reported hosts. 49,50 The evolution of the 1 H NMR spectrum (Figure 5c) of Imicage in the absence/presence of PA was further recorded. The chemical shifts of aromatic protons of Imi-cage were found to move downfield, while the aromatic protons of PA shifted upfield, which demonstrated that the excellent detection sensitivity of Imi-cage likely results from the synergistic effect of hydrogen bonding interactions of both the TPP blocks 51 and the imine groups with the acidic PA, respectively.…”

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confidence: 99%

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Cage-Confinement Induced Emission Enhancement

Tao

Zhao

et al. 2022

J. Phys. Chem. Lett.

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As a proof-of-concept study, Imi-cage and Phos-cage organic molecular cages (OMCs) containing the triphenylphosphine (TPP) moiety, a nonclassic AIE luminogen (AIEgen), have been designed to demonstrate the cage-confinement induced emission enhancement (CCIEE). Thanks to the confinement effect of OMCs, the rigid Imi-cage exhibits much higher photoluminescence (PL) quantum yield (ΦPL) than the open-shell Semicage and small molecule TPP in both solution and amorphous solid states. The emission of Phos-cage could be further enhanced in crystalline solid state with a remarkably high ΦPL of 97.6% (vs 3.47% of crystalline TPP) benefiting from AIE enabled by the highly ordered molecular packing. The novel strategy of CCIEE via confining an AIEgen into an OMC to achieve a significant emission enhancement will shed light on the development of solid-state highly fluorescent materials. The fluorescent nature of Imi-cage was further exploited for the ultrahighly sensitive detection of the explosive picric acid.

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confidence: 55%

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confidence: 99%

Cage-Confinement Induced Emission Enhancement

Tao

Zhao

et al. 2022

J. Phys. Chem. Lett.

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“…The emission of 103 was significantly attenuated (Figure 2C) with increasing amount of TNP in the mixed solution. Huang and coworkers 42 decreased by approximately 90%. Besides metal ions, the fluorescence of Ag I metallacage 119 84 (Scheme 10) can also be quenched by I − and NO 3 − by 28% and 50%, respectively, as a result of the interactions between I − /NO 3 − and Ag + ions.…”

Section: Detecting Explosivesmentioning

confidence: 92%

“…Intriguingly, macrocycle 11 can aggregate to form nanofibers that show a selective affinity to Cu ions. In 2021, Huang and co-workers constructed (Scheme ) two TPE-based [3 + 2] imine nanocages, 12 and 13 , through a one-step condensation reaction between the TPE-based dialdehyde 3 or 4 and tris(2-aminoethyl)amine ( 9 ), respectively, in trichloromethane (CHCl 3 ) in high yields, which, in both solution and the solid state, exhibit typical AIE characteristics and an effective detection ability for various explosives such as nitrobenzene. Such high sensitivity is attributed to the high-density enrichment of nine benzene donors in the frameworks of both cages.…”

Section: Strategies For the Construction Of Tpe-incorporated Macrocyc...mentioning

confidence: 99%

“…Nitroaromatic compounds usually quench fluorescence through a photoinduced-electron-transfer mechanism for their electron-deficient nature. A number of TPE-incorporated macrocycles and nanocages with typical AIE character exhibit (Figure A) an effective detection ability to various explosives. ,,,,, Zheng and co-workers employed an ether-linked TPE macrocycle, 24 (Scheme ), as a sensor to detect nitroaromatic explosives. They found that (Figure B) 24 had a significant detection effect on TNT and 2,4-dinitrotoluene (2,4-DNT) in 10 different explosives involving TNT, 2,4,6-trinitrophenol (TNP), 1,3,5-trinitrobenzene (TNB), DNT, 2,4-dinitrophenol (DNP), 1,3-dinitrobenzene (DNB), 4-nitrotoluene (4-NT), para -nitrophenol (PNP), nitrobenzene (NB), and phenol (P).…”

Section: Applications Of Tpe-incorporated Macrocycles and Nanocagesmentioning

confidence: 99%

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Tetraphenylethylene-Incorporated Macrocycles and Nanocages: Construction and Applications

Bian

Liang

Liu

2022

ACS Appl. Nano Mater.

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Dyes exhibiting aggregation-induced emission (AIE) properties can efficiently circumvent the aggregation-caused quenching phenomenon presented in conventional fluorophores in their solid state. As one of the AIE dyes, tetraphenylethylene (TPE) has attracted tremendous attention because of its concise synthesis, stability, at least four reaction sites, and so on, making it a splendid building block for macrocycles and nanocages. In TPE-incorporated macrocycles and nanocages, the AIE effect can be not only preserved but also enhanced as a result of the geometrical constraint of the otherwise rotatable phenylene rings in the TPE units, which endows them with various applications involving the encapsulation and detection of explosives and dyes. This review surveys the recent developments of TPE-incorporated macrocycles and nanocages all the way from the perspective of synthetic strategies involving dynamic covalent chemistry, covalent bonding, and metal coordination to their potential applications in explosives detection, chemical sensing, cell imaging, and catalysis. Finally, we summarize the state-of-the-art status and challenges in this area, which we hope will guide future investigations.

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Construction and modulation of aggregation‐induced emission materials based on dynamic covalent bonds

Zheng,

Wang,

et al. 2024

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The remarkable advantages and promising application potentials of aggregation‐induced emission (AIE) materials have seen significant advancements in recent years. Notably, AIE materials incorporating dynamic covalent bonds (DCBs) have garnered escalating attention and demonstrated remarkable progress due to their reversible and self‐adaptive properties, thus exhibiting immense potential across various domains including biomedicine, nanomaterials, sensing, and optical displays. This review aims to provide a comprehensive overview of the recent strides in DCBs‐based AIE materials, organized by the types of dynamic covalent bonds utilized, such as Diels–Alder reaction, imine bond, transesterification, boronic ester bond, disulfide bond, [2+2] Cycloaddition Reaction and X‐yne adducts exchange. Through exemplifying representative cases, we elucidate the design principles of chemical structures and the diverse dynamic behaviors exhibited by DCBs‐based AIE materials. Leveraging the principles of dynamic covalent chemistry, these emissive materials can be facilely prepared, and they possess inherent self‐adaptability and responsiveness to stimuli. Finally, we present succinct conclusions and discuss future trends in this burgeoning field, offering fresh insights into the design of novel luminescent materials based on dynamic covalent bonds for broader applications.

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Imine organic cages derived from tetraphenylethylene dialdehydes exhibiting aggregation-induced emission and explosives detection

Cited by 11 publications

References 41 publications

Cage-Confinement Induced Emission Enhancement

Cage-Confinement Induced Emission Enhancement

Tetraphenylethylene-Incorporated Macrocycles and Nanocages: Construction and Applications

Construction and modulation of aggregation‐induced emission materials based on dynamic covalent bonds

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