Dynamic dye emission ON/OFF systems by a furan moiety exchange protocol

Zhang, Qi; Wang, Ying; Gong, Junbo; Zhang, Xin

doi:10.1016/j.dyepig.2020.108652

Cited by 7 publications

(5 citation statements)

References 53 publications

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“…First, due to the reversibility of DA reactions and the differences of TPE-DAs, the exchange DA processes between TPEMI and diverse furan moieties or some other electron-rich dienes can be monitored theoretically . Taking TPE-A and TPE-B as examples, compared with the α-position (TPE-A), the β-position furan derivative (TPE-B) has reduced steric hindrance and optimal spatial configuration, so TPE-B is more competitive than TPE-A in the dynamic exchange reaction . As shown in Figure A(a,b), the reaction between TPE-A and excess 3-furanmethanol was monitored by fluorescence spectra.…”

Section: Resultsmentioning

confidence: 99%

“…51 Moreover, the density functional theory calculation was conducted to get an insight into the different fluorescence behaviors of TPEMI and TPE-A. As shown in Scheme 1C, the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO) energy gaps of TPEMI were small enough for the formation of the charge transfer state, giving reasonable interpretation for complete fluorescence quenching of TPEMI by intramolecular donor-toacceptor charge transfer, 52 while TPE-A possessed high LUMO values, indicating that the electron affinity of the acceptor and charge transfer interaction was weak for TPE-DAs.…”

Section: Resultsmentioning

confidence: 99%

“…40 Taking TPE-A and TPE-B as examples, compared with the α-position (TPE-A), the β-position furan derivative (TPE-B) has reduced steric hindrance and optimal spatial configuration, so TPE-B is more competitive than TPE-A in the dynamic exchange reaction. 52 As shown in Figure 4A(a,b), the reaction between TPE-A and excess 3-furanmethanol was monitored by fluorescence spectra. Because the fluorescence quantum yields of TPE-A and TPE-B were 0.169 and 0.494, respectively, during the exchange reaction, the fluorescence intensity increased with the production of TPE-B.…”

Section: Intermolecularmentioning

confidence: 99%

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In Situ Visualization of Reversible Diels–Alder Reactions with Self-Reporting Aggregation-Induced Emission Luminogens

Mao

Wang

et al. 2022

ACS Appl. Mater. Interfaces

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The dynamic reversible Diels–Alder (DA) reactions play essential roles in both academic and applied fields. Currently, in situ visualization and direct monitoring of the formation and cleavage of covalent bonds in DA reactions are hampered by finite compatibility and expensive precise instruments, especially limited in solid reactions. We herein report a fluorescence system capable of in situ visualization by naked eyes and monitoring DA/retro-DA reactions. With the fluorescence quenching effect, the synthesized TPEMI could work as an innovative self-indicator for both DA termination and retro-DA occurrence. The fluorescence increases during DA reactions, and the mechanism is investigated to establish qualitative and quantitative relations. Besides rapid screening of reaction conditions and monitoring of DA exchange processes, the TPEMI fluorescence system can visualize heterogeneous and solid-state reactions with the AIE character. The TPEMI platform is expected to offer novel insights into reversible DA processes and dynamic covalent chemistry.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Intermolecularmentioning

confidence: 99%

See 1 more Smart Citation

In Situ Visualization of Reversible Diels–Alder Reactions with Self-Reporting Aggregation-Induced Emission Luminogens

Mao

Wang

et al. 2022

ACS Appl. Mater. Interfaces

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“…The two carbon peaks in the aromatic ring are located at 123.7 and 110.6 ppm respectively. Most importantly, the peak at 37.5 ppm is clearly indicative of the methylene carbon that is formed by the Friedel-Crafts alkylation reaction [19,[30][31][32]. Therefore, carbazole monomers have successfully been cross-linked with and thiophene or furan monomers by the methylene bond into the copolymers HCP-CT and HCP-CF.…”

Section: Characterizationmentioning

confidence: 99%

Facile synthesis of novel bi-heteroatom functionalized hyper-crosslinked porous polymers with efficient adsorption methylene blue and methyl orange

Fu,

He,

Guo

et al. 2024

Preprint

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In this work, we designed and synthesized two novel bi-heteroatom functionalized hyper-crosslinked porous polymers (HCP-CT and HCP-CF) through a simple one-step Friedel-Crafts alkylation reaction. The resulted polymers N/S bi-heteroatom functionalized polymer HCP-CT and N/O bi-heteroatom functionalized polymer HCP-CF both have good adsorption properties for organic dyes such as methyl orange (MO) and methylene blue (MB) in aqueous solution due to its rich pore structure, high specific surface area and rich-heteroatoms of pore surface. It is worth mentioned that the maximum adsorption capacity (qmax) of cationic dye MB by the polymer HCP-CT at room temperature was reached up to 1571.46 mg/g, which is much higher than that of most reported porous materials. Furthermore, the adsorption capacity of HCP-CT for the cationic dye MB was more than seven times that of the anionic dye MO (qmax=212.77 mg/g). Also, the polymer HCP-CF for the MB adsorption capacity (qmax=352.11 mg/g) was more than twice higher than that of anionic dye MO (qmax=131.75 mg/g). The above trends may be because of the stronger electrostatic interaction between the negatively charged N-S/O bi-heteroatom of HCP-CT and HCP-CF with the cationic dye MB than that of MO. In addition, the removal percentage of polymers HCP-CT and HCP-CF still remained above 80% after five adsorption-desorption cycles. Hence, this work provided a convenient synthetic route to develop a novel hyper-crosslinked polymer with high capacity for the entrapment of dyes from aqueous solution.

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“…The reversibility of the fmDA cycloadditions used to link diverse chemical, biochemical and inorganic scaffolds was widely applied in the design of dynamic molecular, biomolecular and organic-inorganic hybrid architectures. The DA reaction of an FA or FA ester 3 with maleimides containing aromatic amine groups led to cycloadducts 6 or 7, which exhibit fluorescent behavior and decompose back into non-fluorescent furan and maleimide upon heating (Scheme 2a) [61,62]. Thus, DA cyclization promotes fluorescence in these systems, and thermally induced rDA reaction quenches it.…”

Section: Application Of a Fmda "Click" Approach For The Development Of Dynamic Molecular Biomolecular And Organic-inorganic Hybrid Systemmentioning

confidence: 99%

Diels–Alder Cycloadditions of Bio-Derived Furans with Maleimides as a Sustainable «Click» Approach towards Molecular, Macromolecular and Hybrid Systems

2021

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This mini-review highlights the recent research trends in designing organic or organic-inorganic hybrid molecular, biomolecular and macromolecular systems employing intermolecular Diels–Alder cycloadditions of biobased, furan-containing substrates and maleimide dienophiles. The furan/maleimide Diels–Alder reaction is a well-known process that may proceed with high efficiency under non-catalytic and solvent-free conditions. Due to the simplicity, 100% atom economy and biobased nature of many furanic substrates, this type of [4+2]-cycloaddition may be recognized as a sustainable “click” approach with high potential for application in many fields, such as fine organic synthesis, bioorganic chemistry, material sciences and smart polymers development.

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Dynamic dye emission ON/OFF systems by a furan moiety exchange protocol

Cited by 7 publications

References 53 publications

In Situ Visualization of Reversible Diels–Alder Reactions with Self-Reporting Aggregation-Induced Emission Luminogens

In Situ Visualization of Reversible Diels–Alder Reactions with Self-Reporting Aggregation-Induced Emission Luminogens

Facile synthesis of novel bi-heteroatom functionalized hyper-crosslinked porous polymers with efficient adsorption methylene blue and methyl orange

Diels–Alder Cycloadditions of Bio-Derived Furans with Maleimides as a Sustainable «Click» Approach towards Molecular, Macromolecular and Hybrid Systems

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