Host–guest interaction-induced emission enhancement of amphiphilic AIEgens: a computational study

Yang, Jiaxin; Peng, Qian; Xue, Ruide; Li, Ze-Sheng; Zheng, Xiaoyan

doi:10.1039/d0qm00942c

Cited by 19 publications

(22 citation statements)

References 51 publications

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“…The AIE behavior highly depends on the aggregation state of the hydrophobic TPE units, which is related to the balance of hydrophilicity/hydrophobicity of the polymers. [ 24,44 ] γ ‐CDs can form inclusion complexes with TPE units of TPE‐PEG as evidenced in Figure 1. The host–guest interaction between γ ‐CD and TPE could make the polymer more hydrophilic, dismantles the aggregation, and turn off the fluorescence of the TPE‐PEG in the aqueous medium (Scheme 1B), as demonstrated in our previous study.…”

Section: Resultsmentioning

confidence: 99%

“…The special structure endows itself a good candidate as a host for the formation of inclusion complexes with some hydrophobic guest molecules in aqueous media (for example, cholic acids (CA), adamantane derivatives, and AIE molecules of tetraphenylethylene (TPE) and so on). [15][16][17][18][19][20][21][22][23] The formation of host-guest complex with CDs could alter the hydrophobic molecules more soluble in water and further weaken the aggregated state, [24][25][26][27][28] which was applied to tune the aggregated state and fluorescence of AIE molecule. For example, Tang et al designed a 𝛾-cyclodextrin (𝛾-CD)-TPE hostguest inclusion complex, resulting in the disaggregation of TPE and no fluorescence in water.…”

Section: Introductionmentioning

confidence: 99%

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Multiregulation of Aggregation‐Induced Emission (AIE) via a Competitive Host–Guest Recognition and α‐Amylase Hydrolyzing

Cai

Lin

Qiao

et al. 2022

Macro Chemistry & Physics

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The multiregulation of aggregation‐induced emission (AIE) that responds to external stimuli to finish multifunctions has become a focus of interest in biodiagnosis. Host–guest‐ recognition is an efficient strategy to introduce switchable, reversible, and other functional properties into AIE molecules. Herein, an amphiphilic tetraphenylethylene (TPE) derivative TPE‐PEG is prepared via the simple amidation reaction and chosen as an AIE‐based guest polymer. The aggregated state of TPE‐PEG is altered and the fluorescence of TPE‐PEG can be turned off in the presence of γ‐cyclodextrins (γ‐CDs) due to the formation of host–guest complex between TPE units and γ‐CDs. TPE units in the cavities of γ‐CDs are released free and an aggregated state of TPE‐PEG is restored via the guest competition epistasis of bile acid. Meanwhile, α‐amylase can hydrolyze the host molecules of γ‐CDs, resulting in an aggregated state of TPE‐PEG again and turning the fluorescence on subtly. This reversible multiregulation of fluorescence may meet the multirequirements for the diagnosis in vivo due to the biological nature of α‐amylase and bile acid.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Multiregulation of Aggregation‐Induced Emission (AIE) via a Competitive Host–Guest Recognition and α‐Amylase Hydrolyzing

Cai

Lin

Qiao

et al. 2022

Macro Chemistry & Physics

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“…However, the detailed structure–property relationship that determines the host–guest interaction–induced emission enhancement phenomenon remains elusive. A typical host molecule CD and a TPE derivative (G-3, Scheme 1 ) were taken as examples to study the influence of host–guest interactions on the photophysical properties of AIEgens by multiscale modeling protocol ( Yang et al, 2021 ). MD simulations confirm that the host–guest inclusion complex 2CD/G-3(D) was formed by several cooperatively interplayed non-covalent interactions.…”

Section: Luminescent Properties Of Organic Aggregatesmentioning

confidence: 99%

Section: Luminescent Properties Of Organic Aggregatesmentioning

confidence: 99%

Progress on Exploring the Luminescent Properties of Organic Molecular Aggregates by Multiscale Modeling

Zhao

Zheng

2022

Front. Chem.

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Luminescent molecular aggregates have attracted worldwide attention because of their potential applications in many fields. The luminescent properties of organic aggregates are complicated and highly morphology-dependent, unraveling the intrinsic mechanism behind is urgent. This review summarizes recent works on investigating the structure–property relationships of organic molecular aggregates at different environments, including crystal, cocrystal, amorphous aggregate, and doped systems by multiscale modeling protocol. We aim to explore the influence of intermolecular non-covalent interactions on molecular packing and their photophysical properties and then pave the effective way to design, synthesize, and develop advanced organic luminescent materials.

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“…[39,[48][49][50] The incorporation of AIEgens into amphiphilic polymers can also be realized by non-covalent supramolecular host-guest interactions. [51][52][53] AIEgenic amphiphilic polymers, upon self-assembly in an aqueous medium, yield nanosized, bright fluorescent nanoparticles. Their intrinsic fluorescence and tuneable emission allow AIEgenic aggregates to be widely used in tracking and imaging of many biological events, from in vivo biodistribution and cellular internalization, to drug release.…”

Section: Introductionmentioning

confidence: 99%

Amphiphilic AIEgen‐polymer aggregates: Design, self‐assembly and biomedical applications

et al. 2021

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Aggregation-induced emission (AIE) is a phenomenon in which fluorescence is enhanced rather than quenched upon molecular assembly. AIE fluorogens (AIEgens) are flexible, conjugated systems that are limited in their dynamics when assembled, which improves their fluorescent properties. This intriguing feature has been incorporated in many different molecular assemblies and has been extended to nanoparticles composed of amphiphilic polymer building blocks. The integration of the fascinating AIE design principle with versatile polymer chemistry opens up new frontiers to approach and solve intrinsic obstacles of conventional fluorescent materials in nanoscience, including the aggregation-caused quenching effect. Furthermore, this integration has drawn significant attention from the nanomedicine community, due to the additional advantages of nanoparticles comprising AIEgenic molecules, such as emission brightness and fluorescence stability. In this regard, a range of AIEgenic amphiphilic polymers have been developed, displaying enhanced emission in the self-assembly/aggregated state. AIEgenic assemblies are regarded as attractive nanomaterials with inherent fluorescence, which display promising features in a biomedical context, for instance in biosensing, cell/tissue imaging and tracking, as well as (photo) therapeutics. In this review, we describe recent strategies for the design and synthesis of novel types of AIEgenic amphiphilic polymers via facile approaches including direct conjugation to natural/synthetic polymers, polymerization, post-polymerization and supramolecular host−guest interactions. Their self-assembly behavior and biomedical potential will be discussed.

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Host–guest interaction-induced emission enhancement of amphiphilic AIEgens: a computational study

Abstract: Host–guest interactions, including hydrophobic interactions, intermolecular H-bonds and O–H⋯π interactions, play important roles in the photophysical properties of amphiphilic AIEgens.

Cited by 19 publications

References 51 publications

Multiregulation of Aggregation‐Induced Emission (AIE) via a Competitive Host–Guest Recognition and α‐Amylase Hydrolyzing

Multiregulation of Aggregation‐Induced Emission (AIE) via a Competitive Host–Guest Recognition and α‐Amylase Hydrolyzing

Progress on Exploring the Luminescent Properties of Organic Molecular Aggregates by Multiscale Modeling

Amphiphilic AIEgen‐polymer aggregates: Design, self‐assembly and biomedical applications

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