Measurement of Solubilization Location in Micelles Using Anchored Aggregation‐Induced Emission Donors

Guan, Weijiang; Yang, Tingting; Lu, Chao

doi:10.1002/anie.202005085

Cited by 30 publications

(38 citation statements)

References 63 publications

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“…High FRET efficiency are conducive to the preparation of various monochromatic lights, and moderate FRET efficiency could be used to produce composite lights (for example, white light). [19] The CIE chromaticity diagram in Figure 3b,d exhibited the colortuning maps with adjusting the concentration of acceptor. More importantly, in the PYC12/COONa-γ-CD/NiR triad assembly, with the addition of NiR to PYC12/COONa-γ-CD assembly, the emission color changed from cyan to red, which included the whitelight emission with the chromaticity coordinates in (0.32, 0.30).…”

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Photocontrolled Light‐Harvesting Supramolecular Assembly Based on Aggregation‐Induced Excimer Emission

Zhang

Liu

et al. 2020

Advanced Optical Materials

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should be relatively high. [9] Considering the advantages of host-guest interaction, supramolecular assembly with macrocycle has turned out to be a useful approach to develop aqueous light-harvesting systems. [10] For example, Tang and co-workers reported an efficient light-harvesting system with ultrahigh antenna effect based on aggregation-induced enhanced emission (AEE) conjugated polymeric supramolecular network. [11] Anderson and co-workers synthesized a complex comprising a cyanine dye rotaxane and a porphyrin nanoring as a model light-harvesting system. [12] Wang and coworkers fabricated highly efficient artificial light-harvesting systems based on supramolecular selfassembly. [4a,13] Our group also developed aqueous light-harvesting systems with efficient energy transfer efficiency. [14] Antenna chromophores with distinct fluorescence property play a significant role in light-harvesting systems. In this regard, some people have paid increasing attention to improving the photophysical properties of optical materials to achieve high quantum yield, strong emission, and broad color emission. [15] Traditional luminophores have suffered from the undesired ACQ effect in aggregated state because of intermolecular compact π-π stacking, which severely limits their further applications in aqueous solution. On the contrary, organic fluorogens with aggregation-induced emission are highly emissive in aggregated state, which exhibits remarkable advantages to construct light-harvesting systems. [16] However, fluorophores with stacked-induced excimer emission characteristics typically provide a broad spectrum with the maximum red-shifted around 100 nm in aggregated state compared to monomer emission, [17] which overcomes the ACQ effect and is not restricted to the UV or blue regions in water. Therefore, constructing light-harvesting systems by tuning a single fluorophore's photoluminescence from monomer emission in monomeric state to excimer emission in aggregated state was rarely reported to our knowledge. Herein, we fabricated novel photo-controlled light-harvesting system based on the supramolecular assembly of polyanionic γ-cyclodextrin (COONa-γ-CD), pyrene derivative (PYC12), Nile red (NiR), and diarylethene derivative (DAE) in aqueous solution (Scheme 1). PYC12 displays intense fluorescence emission at 375 and 395 nm in isolated or monomeric state, whereas they produce strong red-shift excimer emission at 490 nm in the aggregated state. COONa-γ-CD could induce efficient aggregation into well-ordered PYC12/COONa-γ-CD Photocontrolled light-harvesting supramolecular assembly with aggregation-induced excimer emission is fabricated by polyanionic γ-cyclodextrin (COONa-γ-CD), pyrene derivative (PYC12), Nile red (NiR), and diarylethene derivative (DAE) in aqueous solution. Benefiting from the COONa-γ-CDinduced aggregation of PYC12, the fluorescence can be modulated from monomeric state to assembled state with a large red-shift around 100 nm, which exhibits aggregation-induced excimer emission enhancement and makes PYC12 a ...

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Photocontrolled Light‐Harvesting Supramolecular Assembly Based on Aggregation‐Induced Excimer Emission

Zhang

Liu

et al. 2020

Advanced Optical Materials

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“…Similarly,p ara-hydroxy-TPE (TPE-OH) reacted with 1,12dibromododecane to form TPE-C 12 Br. [22] In the presence of TiCl 4 and zinc dust, McMurry coupling of BP-C 4 Br and BP-C 8 ,and BP-C 8 Br and BP-C 4 could produce C 8 -TPE-C 4 Br and C 4 -TPE-C 8 Br. [23] Their molecular structures were verified using 1 Hn uclear magnetic resonance ( 1 HNMR) spectra (Supporting Information, Figures S2-S4).…”

Section: Resultsmentioning

confidence: 98%

“…In detail, under basic conditions, 4‐hydroxybenzophenone (BP‐OH) was converted into BP‐C 4 Br, BP‐C 8 , BP‐C 8 Br, and BP‐C 4 by reacting with 1,4‐dibromobutane, 1‐bromooctane, 1,8‐dibromooctane, and 1‐bromobutane, respectively. Similarly, para‐hydroxy‐TPE (TPE‐OH) reacted with 1,12‐dibromododecane to form TPE‐C 12 Br [22] . In the presence of TiCl 4 and zinc dust, McMurry coupling of BP‐C 4 Br and BP‐C 8 , and BP‐C 8 Br and BP‐C 4 could produce C 8 ‐TPE‐C 4 Br and C 4 ‐TPE‐C 8 Br [23] .…”

Section: Resultsmentioning

confidence: 99%

“…Their molecular structures were verified using 1 H nuclear magnetic resonance ( 1 H NMR) spectra (Supporting Information, Figures S2–S4). Thereafter, three bromine‐functionalized intermediates (C 8 ‐TPE‐C 4 Br, C 4 ‐TPE‐C 8 Br, and TPE‐C 12 Br) were reacted with excess trimethylamine to afford three target products: C 8 ‐TPE‐C 4 TAB, C 4 ‐TPE‐C 8 TAB, and TPE‐C 12 TAB [22] . The 1 H NMR spectra (Figure 1) indicated that all hydrogen atoms were in the correct positions and the corresponding peak integrations were consistent with their structures.…”

Section: Resultsmentioning

confidence: 99%

“…Chemie Forschungsartikel 13140 www.angewandte.de ure S13). [22,24] Thef luorescence quantum yields of the three micelle solutions (80 mM) were 8.45 %, 15.19 %, and 9.10 %, indicating that the TPE groups could intensely emit in the micelles.I na ddition, the spectral overlap between donor emission and acceptor absorption was essential for RET to occur. [27][28][29] As shown in Figure 2d,t he CL spectrum of luminol was recorded in the presence of 5mMo fH 2 O 2 and 10 mMo fC o 2+ ,w hich could overlap with the absorption spectra of the micelle solutions of C 8 -TPE-C 4 TAB, C 4 -TPE-C 8 TAB, and TPE-C 12 TAB.…”

Section: Methodsmentioning

confidence: 99%

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Chemiluminescence Resonance Energy Transfer Efficiency and Donor–Acceptor Distance: from Qualitative to Quantitative

et al. 2021

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Since its birth in 1967, the utilization of chemiluminescence resonance energy transfer (CRET) has made substantial progress in av ariety of fields for its unique features. However,t he quantitative relationship between CRET efficiency and donor-acceptor distance has not yet been determined owing to the difficulty in designing the variable lengths between chemiluminescent donors and acceptors.H erein, we synthesized three kinds of tetraphenylethene (TPE)-anchored cationic surfactants with aggregation-induced emission (AIE) characteristics.F or the first time,i ti sq uantitatively demonstrated that the CRET efficiency is inversely proportional to the sixth power of distance between luminol donors and TPE acceptors.T he details disclosed in this contribute have provided the solid evidence that CRET follows Fçrster resonance theory.O ur strategy would build ap romising platform to control donor-acceptor distance,a llowing to the interdisciplinary applications of CRET.

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Steric Barrier‐Steered Reaction Sites in Micellar Catalysis

Zhang

Yin

Guan

et al. 2023

Advanced Optical Materials

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In the pursuit of an advanced micellar catalysis system, the reaction sites in micelles determine its catalytic performances. However, the intrinsic polarity gradient of micelles anchors the reactants in the fixed regions, leading to an unmet challenge to steer the reaction sites to the optimal ones. To overcome this limitation, a Förster resonance energy transfer (FRET) spectroscopic ruler is established to position the true sites of reactants in micellar catalysis by using tetraphenylethylene (TPE) in the aggregation‐induced emission (AIE) micelles as the FRET donor and Nile red as the FRET acceptor. Subsequently, the customizable TPE steric barriers in the AIE micelles are apt to mediate the reactants into the polar micellar surface, the semipolar palisade layer, or the nonpolar internal layer, achieving the corresponding catalytic efficiencies. Additionally, the universality of steric barrier‐steered reaction sites in micellar catalysis is further demonstrated by the simple incorporation of small nonpolar molecules into the commercially available surfactants. To the authors’ knowledge, this is the first report on the design of steric barriers to steer the reaction sites in micellar catalysis. These findings open up attractive perspectives for the exploration of new classes of efficient micellar catalysis systems in a variety of reactions.

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Measurement of Solubilization Location in Micelles Using Anchored Aggregation‐Induced Emission Donors

Cited by 30 publications

References 63 publications

Photocontrolled Light‐Harvesting Supramolecular Assembly Based on Aggregation‐Induced Excimer Emission

Photocontrolled Light‐Harvesting Supramolecular Assembly Based on Aggregation‐Induced Excimer Emission

Chemiluminescence Resonance Energy Transfer Efficiency and Donor–Acceptor Distance: from Qualitative to Quantitative

Steric Barrier‐Steered Reaction Sites in Micellar Catalysis

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