Facile synthesis of cross-linked patchy fluorescent conjugated polymer nanoparticles by click reactions

İbrahimova, Vüsala; Ekiz, Seyma; Gezici, Özlem; Tuncel, Dönüş

doi:10.1039/c1py00332a

Cited by 29 publications

(30 citation statements)

References 40 publications

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“…Briefly, the reaction of 2-bromofluorene with 1,3-dibromopropane in the presence of aqueous solution of NaOH afforded 2-bromo-9,9-bis(3-bromopropyl)-9H-fluorene (M1). 3,4 The reaction of M1 with tributylvinyltin in toluene in the presence of palladium catalyst gave 9,9-bis(3-bromo-propyl)-2-vinyl-9H-flourene, M2. Then, the compound M2 was reacted with dimethyl amine to yield 3,3′-(2-vinyl-9H-flourene-9,9-diyl)-bis(N,N-dimethylpropane-1-amine), M3.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Red Emitting, Cucurbituril-Capped, pH-Responsive Conjugated Oligomer-Based Nanoparticles for Drug Delivery and Cellular Imaging

et al. 2014

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Here we report the synthesis of nanoparticles based on a conjugated oligomer which is synthesized through Heckcoupling of divinylfluorene and dibromobenzothiodiazole monomers. These water dispersible nanoparticles emit in the region of red tailing to the near-infrared region of the spectrum with high fluorescent quantum yield and brightness. The nanoparticles were found to be stable in water for a prolonged time without forming any aggregates and could carry camptothecin, an anticancer drug with high loading efficiency. MTT cell viability studies performed with breast cancer cell lines showed that halfmaximal inhibitory concentration (IC 50 ) values of nanoparticles for MCF7 and MDA-MB-231 were 44.7 μM and 24.8 μM, respectively. In order to further decrease the cytotoxicity and increase the stability of nanoparticles, amine groups were disguised by capping with cucurbit [7]uril (CB7). Drug release studies showed that drugs were released at low pH (at 5.0) faster than physiological pH (7.4) confirming the pH-responsive nature of the nanoparticles. On the other hand, CB7-capped drug-loaded nanoparticles regulated the release rate by providing slower release at pH 7.4 than the nanoparticles in the absence of CB7s. IC 50 values for camptothecin in the presence of nanoparticles with or without CB7 were significantly reduced in MCF7 and MDA-MB-231 cells. ■ INTRODUCTIONConjugated polymer nanoparticles (CPNs) are highly appealing for various advanced applications such as in vivo imaging, cell labeling, and delivery of therapeutic agents, as well as nanophotonics, owing to their high quantum yields and molar absorptivity, tunable properties, easy functionalization, photostability, and so forth. 1−7 To date, the use of CPNs has been demonstrated successfully in cell imaging, oxygen sensing, drug delivery, and nucleic acid delivery. 8−16 When these nanostructures are judiciously designed, they can be utilized in theranostic applications by combining more than one functionality to deliver therapeutic and imaging agents. 17−21 For the controlled delivery of therapeutic agents to the targets the nanoparticles could also include responsive groups that will respond to stimuli such as pH, oxidation−reduction, and enzymes. However, in the literature, examples are scarce regarding the multifunctional conjugated polymer nanoparticles (CPNs) and even less with conjugated oligomer-based nanoparticles (CONs). 22,23 Recently, Schenning et al. compared the capabilities of conjugated polymer nanoparticles to selfassembled oligomer-based nanoparticles in terms of their fluorescent quantum yields, stabilities, molar absorptivity, guest-holding, and releasing. 24 They demonstrated that oligomer nanoparticles have higher fluorescent quantum yields and comparable stabilities and molar absorptivity, but they release the guest faster than the conjugated polymer nanoparticles. Thus, this feature should be considered for the further design of oligomer-based nanoparticles for theranostic applications. CONs also offer some useful addi...

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Section: ■ Results and Discussionmentioning

confidence: 99%

Red Emitting, Cucurbituril-Capped, pH-Responsive Conjugated Oligomer-Based Nanoparticles for Drug Delivery and Cellular Imaging

et al. 2014

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“…The precipitates were collected by suction and dried under vacuum for 6 h (547 mg, 56%). The synthesis of PFBT-Br can also be found in ref 27. Preparation of PFBT-Br Nanoparticles.…”

Section: ■ Materials and Experimental Methodologymentioning

confidence: 99%

Morphology-Dependent Energy Transfer of Polyfluorene Nanoparticles Decorating InGaN/GaN Quantum-Well Nanopillars

et al. 2013

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Conjugated polymer nanoparticles (CPNs), prepared in aqueous dispersion from poly[(9,9-bis{3-bromopropyl}fluorenyl-2,7-diyl)-co-(1,4-benzo-{2,1,3}-thiodiazole)] (PFBT-Br), are incorporated into a nanopillar architecture of InGaN/GaN multiple quantum wells (MQWs) to demonstrate a new organic/inorganic class of nanostructured excitonic model system. This hybrid system enables intimate integration for strong exciton−exciton interactions through nonradiative energy transfer (NRET) between the integrated CPNs and MQW pillars. The NRET of these excitonic systems is systematically investigated at varied temperatures. In these hybrids, InGaN/GaN MQWs serve as the donor of the NRET pair, while immobilized PFBT-Br polymer serves as the acceptor. To understand morphology-dependent NRET, PFBT-Br CPNs coating InGaN/GaN MQWs are made to defold into polymer chains by in situ treatment with a good solvent (THF). The experimental results indicate that NRET is significantly stronger in the case of CPNs compared with their defolded polymer chains. At room temperature, while the NRET efficiency of open polymer chains−nanopillar system is only 10%, PFBT-Br CPNs exhibit a substantially higher NRET efficiency of 33% (preserving the total number of polymer molecules). The NRET efficiency of the nanoparticle systems is observed to be 25% at 250 K, 22% at 200 K, 19% at 150 K, and 15% at 100 K. On the other hand, the defolded polymer chains exhibit significantly lower NRET efficiencies of 17% at 250 K, 16% at 200 K, 11% at 150 K, and 5% at 100 K. This work may potentially open up new opportunities for the hybrid organic/inorganic systems where strong excitonic interactions are desired for light generation, light harvesting, and sensing applications. C onjugated polymer nanoparticles (CPNs) attract significant attention for important applications including bioimaging, 1−3 biosensing, 4,5 and optoelectronics. 6−12 One of the most attractive features of CPNs is the convenient tunability and control of their properties through the choice and functionalization of the polymer and the surface modification of nanoparticles. Furthermore, CPNs exhibit low toxicity, 13 and their mechanical stability can be enhanced through cross-linking.14 Their optical properties arise from the controlled conformational changes of the polymer and their aggregation form rather than the quantum confinement effects, in contrast with inorganic nanoparticles, for example, colloidal semiconductor quantum dots (QDs).13 As a result of these attractive properties, CPNs find use as alternative color convertors, or molecular beacons, in various biotechnology 1,3,4 and optoelectronic applications. 6,9,10,13,14 The emission of color convertors, including CPNs, can be enhanced via the Forster-type nonradiative energy transfer (NRET) (also dubbed as Forster resonance energy transfer, FRET), which basically relies on the exciton−exciton interactions between the donor and acceptor emitters. 15 For example, polymers, 16 organic dyes, 17 inorganic QDs, 18 and epitaxial quan...

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“…To date, a variety of luminescent polymeric nanoparticles based on conventional organic dyes, conjugated polymers, aggregation‐induced emission (AIE) dyes, and polydopamine have been reported . The basic principle for the formation of luminescent polymeric nanoparticles is the incorporation of hydrophobic dyes into amphiphilic polymers, which can be readily self‐assembled into core–shell organic nanoparticles in aqueous solution .…”

Section: Introductionmentioning

confidence: 99%

Preparation and Bioimaging Applications of AIE Dye Cross-linked Luminescent Polymeric Nanoparticles

et al. 2014

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With the ever increasing interest in biomedical applications of luminescent probes, the development of novel luminescent nanoparticles which showed high water dispersibility, strong luminescence and excellent biocompatibility has been extensively pursued. In this work, cross-linked luminescent polymeric nanoparticles based on aggregation induced emission (AIE) dyes were fabricated through combination of free radical polymerization and ring-opening reaction using AIE dye as the fluorogen and linker simultaneously. Our results demonstrated that these AIE dye based cross-inked polymeric nanoparticles showed high water dispersibility, remarkable luminescent properties and excellent biocompatibility, is highly potential for biomedical applications.

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Facile synthesis of cross-linked patchy fluorescent conjugated polymer nanoparticles by click reactions

Cited by 29 publications

References 40 publications

Red Emitting, Cucurbituril-Capped, pH-Responsive Conjugated Oligomer-Based Nanoparticles for Drug Delivery and Cellular Imaging

Red Emitting, Cucurbituril-Capped, pH-Responsive Conjugated Oligomer-Based Nanoparticles for Drug Delivery and Cellular Imaging

Morphology-Dependent Energy Transfer of Polyfluorene Nanoparticles Decorating InGaN/GaN Quantum-Well Nanopillars

Preparation and Bioimaging Applications of AIE Dye Cross-linked Luminescent Polymeric Nanoparticles

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