Nanoparticles with Near-Infrared Emission Enhanced by Pillararene-Based Molecular Recognition in Water

Shi, Bingbing; Jie, Kecheng; Zhou, Yujuan; Zhou, Jiong; Xia, Danyu; Huang, Feihe

doi:10.1021/jacs.5b11676

Cited by 282 publications

(177 citation statements)

References 51 publications

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“…Compared with other fluorophores such as small molecules and quantum dots, they are advantageous as biomaterials because of their good biocompatibility, ease of preparation, and biomimetic character (4)(5)(6). Conventional fluorophores show good emission in dilute solution but experience varying degrees of aggregation-caused quenching due to the intense intermolecular interactions, which will decay or relax the excited state back to the ground state via nonradiative channels (7).…”

mentioning

confidence: 99%

Fluorescent metallacycle-cored polymers via covalent linkage and their use as contrast agents for cell imaging

Zhang

Shu-ya

Yan

et al. 2016

Proc. Natl. Acad. Sci. U.S.A.

113

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The covalent linkage of supramolecular monomers provides a powerful strategy for constructing dynamic polymeric materials whose properties can be readily tuned either by the selection of monomers or the choice of functional linkers. In this strategy, the stabilities of the supramolecular monomers and the reactions used to link the monomers are crucial because such monomers are normally dynamic and can disassemble during the linking process, leading to mixture of products. Therefore, although noncovalent interactions have been widely introduced into metallacycle structures to prepare metallosupramolecular polymers, metallacyclecored polymers linked by covalent bonds have been rarely reported. Herein, we used the mild, highly efficient amidation reaction between alkylamine and N-hydroxysuccinimide-activated carboxylic acid to link the pendent amino functional groups of a rhomboidal metallacycle 10 to give metallacycle-cored polymers P1 and P2, which further yielded nanoparticles at low concentration and transformed into network structures as the concentration increased. Moreover, these polymers exhibited enhanced emission and showed better quantum yields than metallacycle 10 in methanol and methanol/water (1/9, vol/vol) due to the aggregationinduced emission properties of a tetraphenylethene-based pyridyl donor, which serves as a precursor for metallacycle 10. The fluorescence properties of these polymers were further used in cell imaging, and they showed a significant enrichment in lung cells after i.v. injection. Considering the anticancer activity of rhomboidal Pt(II) metallacycles, this type of fluorescent metallacycle-cored polymers can have potential applications toward lung cancer treatment.fluorescent polymers | supramolecular coordination complex | covalent linkage | aggregation-induced emission | cell imaging F luorescent polymers have received much attention in the chemical and life sciences due to their promising applications in biological labeling, tracking, monitoring, imaging, and diagnostics (1-3). Compared with other fluorophores such as small molecules and quantum dots, they are advantageous as biomaterials because of their good biocompatibility, ease of preparation, and biomimetic character (4-6). Conventional fluorophores show good emission in dilute solution but experience varying degrees of aggregation-caused quenching due to the intense intermolecular interactions, which will decay or relax the excited state back to the ground state via nonradiative channels (7). Such fluorophores are not ideal candidates for the preparation of fluorescent polymers, because they need to be aggregated by the polymerization process, which will more or less decrease the fluorescence emissions and the quantum yields of the derived fluorescent polymers.In 2001, Tang and coworkers (8) reported an opposite fluorescence effect named as aggregation-induced emission (AIE). In such cases, fluorophores are nearly nonemissive as discrete molecules, but they exhibit strong fluorescence in concentrated solution or in the s...

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mentioning

confidence: 99%

Fluorescent metallacycle-cored polymers via covalent linkage and their use as contrast agents for cell imaging

Zhang

Shu-ya

Yan

et al. 2016

Proc. Natl. Acad. Sci. U.S.A.

113

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“…No obvious shifts were observed for protons H f– h because G′ is too long to be wrapped completely in the cavity of WP5 . Peaks related to protons H 1–3 on WP5 slightly shifted downfield and peak of proton H 1 was broader than that before complexation, which provided further evidence to prove the formation of host–guest supramolecular complex WP5⊃G′ . A 2D nuclear overhauser effect spectroscopy (NOESY) NMR spectrum was further conducted to investigate the complexation between WP5 and G′ (Figure S5, Supporting Information).…”

Section: Resultsmentioning

confidence: 89%

Visible Light–Induced Supra‐Amphiphilic Switch Leads to Transition from Supramolecular Nanosphere to Nanovesicle Activated by Pillar[5]arene‐Based Host–Guest Interaction

Yao

Lü

et al. 2018

Macromol. Rapid Commun.

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A photoresponsive host-guest supramolecular complex (WP5⊃G) constructed by water-soluble pillar[5]arene (WP5) and spiropyran derivative (G) is presented. The spontaneous isomerization of G from spiropyran (SP) form to ring-opened merocyanine (MC) form happens either alone or in WP5⊃G in aqueous media. Irradiated by visible light, G can be converted into SP form completely and the hydrophilicity will be changed. G and WP5⊃G are both verified to self-assemble into nanospheres. Upon exposure to visible light, WP5⊃G reassemble into nanovesicles due to the change of supra-amphiphilicity, while G alone does not have this transition. Obviously, WP5 takes the key role that activates the photoinduced morphological transition.

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“…In particular, water-soluble pillararenes are of significance as prosperous hosts for various guests of biological importance [23][24][25][26][27][28]. With their ease of synthetic manipulation, completely different host-guest systems can be realized through the pillararene scaffold [29,30]. Amongst the most studied, carboxylato-pillar [5]arene [23] forms complexes with paraquat, various amines and basic amino acids [31] that can be exploited to compile FID assays for these analytes [32][33][34][35][36].Cationic, ammonium-containing pillar [5]arene was used as receptor in a FID sensor for various phenols [37].…”

Section: Introductionmentioning

confidence: 99%

Pillararene-based fluorescent indicator displacement assay for the selective recognition of ATP

Bojtár

Kozma

Szakács

et al. 2017

Sensors and Actuators B: Chemical

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Nanoparticles with Near-Infrared Emission Enhanced by Pillararene-Based Molecular Recognition in Water

Cited by 282 publications

References 51 publications

Fluorescent metallacycle-cored polymers via covalent linkage and their use as contrast agents for cell imaging

Fluorescent metallacycle-cored polymers via covalent linkage and their use as contrast agents for cell imaging

Visible Light–Induced Supra‐Amphiphilic Switch Leads to Transition from Supramolecular Nanosphere to Nanovesicle Activated by Pillar[5]arene‐Based Host–Guest Interaction

Pillararene-based fluorescent indicator displacement assay for the selective recognition of ATP

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