Fluorescent Nanoparticles Based on Self‐Assembled <i>π</i>‐Conjugated Systems

Kaeser, AG Adrien; Schenning, Aphj Albert

doi:10.1002/adma.201000427

Cited by 285 publications

(238 citation statements)

References 117 publications

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“…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.…”

Section: ■ Introductionmentioning

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: ■ Introductionmentioning

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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“…Conjugated polymer nanoparticles (CPNs) have attracted a board attention from home and abroad scholar because of their easy synthesis, less toxicity and more biocompatibility [5]. In the past few years, their preparation methods and functional modifications have been explored [6][7][8]. In this paper, novel fluorescent conjugated polymers (TEB) were synthesized by Wittig and Wittig-Horner reaction, and the average molecular weight was improved effectively by Wittig-Horner reaction.…”

Section: Introductionmentioning

confidence: 99%

The Preparation and Fluorescence of Conjugated Polymer Nanoparticles with Triphenylamine Derivatives

Zhu¹,

Zhang²,

Qin³

et al. 2014

Proceedings of the 2015 International Conference on Material Science and Applications

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Abstract. The conjugated polymers TEB1 and TEB2 were synthesized by Wittig and Wittig-Horner reaction, and the conjugated polymer nanoparticles CPNs1 and CPNs2 were prepared by reprecipitation method with TEB1 and TEB2, respectively. Moreover, the morphology and fluorescence of CPNs were investigated. The synthetic results indicated that the average molecular weight was improved effectively by Wittig-Horner reaction. CPNs2 with a higher average molecular weight showed a better feature and bright fluorescence.

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“…An extensive pioneering structural study has been performed by Lee and co-workers [108,109], using a large variation of π-conjugated oligomers. The inherent characteristics of supramolecular self-assembly may exhibit predictable advantages such as a convenient preparation process, tunable properties and multi-functionality [70]. Solution-phase self-assembly of supramolecular CPs offers a powerful alternative to the thinfilm techniques [55].…”

Section: Introductionmentioning

confidence: 99%

“…The extensively used templates include surfactant micelles and aggregates [144]. Surfactant molecules such as hexadecyltrimethylammonium bromide (CTAB) [145], sodium dodecylsulfate (SDS) [146], a triblock copolymer and (PEO) 20 -(PPO) 70 -(PEO) 20 (Pluronic P123) have been explored as soft templates, acting as the segregates for nanostructures. Other useful soft templates for the synthesis of one-dimensional nanostructures include amphiphilic molecules, copolymers [147], liquid crystals, polymer nanofibres and self-assembled monolayers, biological molecules and macromolecular self-organized structures.…”

Section: Introductionmentioning

confidence: 99%

Fluorene-based macromolecular nanostructures and nanomaterials for organic (opto)electronics

Xie

Yang

Lin

et al. 2013

Phil. Trans. R. Soc. A.

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Nanotechnology not only opens up the realm of nanoelectronics and nanophotonics, but also upgrades organic thin-film electronics and optoelectronics. In this review, we introduce polymer semiconductors and plastic electronics briefly, followed by various top-down and bottom-up nano approaches to organic electronics. Subsequently, we highlight the progress in polyfluorene-based nanoparticles and nanowires (nanofibres), their tunable optoelectronic properties as well as their applications in polymer light-emitting devices, solar cells, field-effect transistors, photodetectors, lasers, optical waveguides and others. Finally, an outlook is given with regard to four-element complex devices via organic nanotechnology and molecular manufacturing that will spread to areas such as organic mechatronics in the framework of robotic-directed science and technology.

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Fluorescent Nanoparticles Based on Self‐Assembled π‐Conjugated Systems

Cited by 285 publications

References 117 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

The Preparation and Fluorescence of Conjugated Polymer Nanoparticles with Triphenylamine Derivatives

Fluorene-based macromolecular nanostructures and nanomaterials for organic (opto)electronics

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