Tailor-Made Conjugated Polymer Nanoparticles for Multicolor and Multiphoton Cell Imaging

Abstract

Sonogashira coupling of dibromo- and diethynyl-substituted benzenes and fluorenes in aqueous mini-emulsion afforded colloidally stable dispersions of highly fluorescent 60-120 nm particles of poly(arylene ethynylene)s of molecular weights M(n) 4 × 10(4)-2 × 10(5) g mol(-1) with solids contents up to 15 wt %. By covalent incorporation of diethynyl pyrrolo-pyrrole or diethynyl fluorenone in the mini-emulsion polymerization the emission color of these photostable nanoparticles can be tuned from blue (λ(em max) 470) to orange at a given excitation wavelength due to an efficient energy transfer to these acceptors. Two-photon action cross sections of the particles amount to 10(6) to 10(7) GM. The particles from emulsion polymerization are taken up by HeLa cells without an adverse effect on the cells. Differentiation of the location in cells of particle species varying in emission color was demonstrated for both linear and two-photon excitation microscopy in the NIR regime.

Highly Luminescent Conjugated Polymer Nanoparticles for Imaging and Therapy

“…In order to meet the needs of multiplexed biological imaging, CPNs have also been made for multicolor cell imaging. 60-120 nm particles of highly fluorescent poly(arylene ethynylene)s that were copolymerized with dibromo-substituted fluorenone showed emissions ranging from blue to orange color [24]. Fluorescent quantum yields increased with dye incorporation from 44% to over 60% and photostability studies showed a high tolerance of the CPNs to bleaching; after 500s of irradiation, there was no decrease in fluorescence.…”

Stark fluoreszierende halbleitende Polymerpunkte für Biologie und Medizin

“…[40][41][42][43][44] Es gab beachtliche Bemühungen, vielseitige halbleitende Polymernanopartikel (eine kleine Untergruppe davon sind die P-Punkte) zu erzeugen, ihre Eigenschaften und Funktionen einzustellen und deren Leistung für biomedizinische Untersuchungen zu verbessern. Die Forschungsbemühungen umfassen die Nutzung neuer Herstellungsverfahren, [45,46,69,70,72] die Untersuchung von NanopartikelBildungsmechanismen, [120,121] Sondierung der Photophysik der Nanopartikel, [47,49,54,122,123] Charakterisierung der Fluoreszenzleistung, [48,51,56,58] Abstimmung der Emissionsfarbe, [47,49,71,89] das Manipulieren der Partikeloberflä-che, [56-58, 64-66, 98, 102] die Verkapselung von anorganischen Materialien, [96,97,99,104,105] Entwicklung von Nanopartikelsensoren, [52,59,60,62,74,77] die Bildung von zellulären Strukturen, [56,57,[63][64][65][66] sowie das In-vivo-"Targeting" bei kleinen Tieren. [58,…”

“…[130,131] Erst kürzlich wurde dieser Ansatz auf fluoreszierende halbleitende Polymere ausgeweitet, um daraus Nanopartikel herzustellen. [69][70][71]132] [94,95] allerdings waren die Partikel etwa 250 nm groß und wiesen eine relativ geringe Fluorophorkonzentration auf (ca. 1 Gew.-%).…”

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

“…Recently, an excellent study by Kuehne et al [111] demonstrated that the highly monodisperse nanoparticles of PF-01f (PFO-co-F2/6), PF-04a (F8BT) and PF-15 could be prepared via Suzuki-Miyaura dispersion polymerization using a surfactant mixture of poly(1-vinylpyrrolidone-co-vinyl acetate), Triton X-45 and 1-propanol, which these monodisperse particles readily self-assemble into photonic crystals that exhibit a pronounced photonic stopgap. Nanoparticles of PF-07 and PF-09a-d have been reported via Knoevenagel and Sonogashira coupling emulsion polymerization, respectively [182][183][184]. Re-precipitation is an alternative method for obtaining hydrophobic nanoparticles, which was first employed for producing PF-based nanoparticles, as reported by McNeill and co-workers [191].…”

“…PF-CPNs can be further functionalized by cross-linking, blending, encapsulation and surface modification (figure 4), which have more advantages over the precursor nanoparticles for [104]; PF-01a and 06 from [177]; PF-01e and 15 from [111]; PF-07 from [182]; PF-09a, 09b and 9c from [183,184]; PF-04a from [111,185]; PF-04c from [186]; PF-04e, 08a and 08b from [187,188]; PF-10a from [189]; PF-01b from [190]; PF-01c from [191]; PF-03c from [192]; PF-03d and 3e from [193]; PF-04b from [194]; PF-10b from [195]; PF-16 from [176]; PF-17a from [180]; PF-17b from [173]; PF-04a and PF-05 or PF-01f and PF-02 from [163]; PF-3a, 3b and 12b from [196,197]; PF-11 from [198]; PF-12a from [199]; PF-18 from [200]; PF-13 from [201]; and PF-14b-14e from [202]. (Online version in colour.)…”