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Two anionic fluorene-thiophene alternating copolymers, poly[9,9-bis(4-sulfonylbutoxyphenyl)fluorene-2,7-diyl-2,5-thienylene] (PBS-PFT) and poly[9,9-bis(4-sulfonylbutoxyphenyl)fluorene-2,7-diyl-2,2'-bithiophene-5,5'-diyl] (PBS-PF2T), have been synthesized and their solution behaviors in water studied by UV-vis absorption spectroscopy, fluorescence, and electrical conductivity and compared with that of the previously studied conjugated polyelectrolyte (CPE) poly[9,9-bis(4-sulfonylbutoxyphenyl)fluorene-2,7-diyl-1,4-phenylene] (PBS-PFP). These conjugated polymers do not form solutions at the molecular level in water but instead form clusters. Information on the structure of these clusters for PBS-PF2T comes from small-angle X-ray and neutron scattering. The relative ease of dispersing the copolymers in water increases with an increase in the number of thiophene rings in these alternating copolymers. Semiempirical calculations on the structure suggest that this results from bending of the chains and increased conformational flexibility, decreasing interchain interactions. These CPEs can be dissolved in water at the molecular level using the nonionic surfactants n-dodecylpentaoxyethylene glycol ether (C12E5) or Triton X-100 to obtain systems with increased photoluminescence quantum yield and increased electrical conductivity that can be solution-processed for potential applications as components of sensory or optoelectronic devices.
ACS Appl Mater Interfaces 2009 Apr
PMID:Aqueous solution behavior of anionic fluorene-co-thiophene-based conjugated polyelectrolytes. 2035 13

In an effort to favor the formation of straight polymer chains without crystalline grain boundaries, we have synthesized an amphiphilic conjugated polyelectrolyte, poly(fluorene-alt-thiophene) (PFT), which self-assembles in aqueous solutions to form cylindrical micelles. In contrast to many diblock copolymer assemblies, the semiconducting backbone runs parallel, not perpendicular, to the long axis of the cylindrical micelle. Solution-phase micelle formation is observed by X-ray and visible light scattering. The micelles can be cast as thin films, and the cylindrical morphology is preserved in the solid state. The effects of self-assembly are also observed through spectral shifts in optical absorption and photoluminescence. Solutions of higher-molecular-weight PFT micelles form gel networks at sufficiently high aqueous concentrations. Rheological characterization of the PFT gels reveals solid-like behavior and strain hardening below the yield point, properties similar to those found in entangled gels formed from surfactant-based micelles. Finally, electrical measurements on diode test structures indicate that, despite a complete lack of crystallinity in these self-assembled polymers, they effectively conduct electricity.
ACS Nano 2013 Feb 26
PMID:Self-assembling semiconducting polymers--rods and gels from electronic materials. 2334 27

Conjugated polymer nanoparticles composed of PFT/PS as a core and PEG-COOH on the surface were prepared by a reprecipitating method. The CPNs diaplay excellet properties such as good photostability, low cytotoxicity, and strong brightness, etc. The average diamater of CPNs is 30 nm with a spherical morphology. To realize specific imaging in different parts of tumor cells, the bare CPNs with the carboxyls on the surface were conjugated with antibody or peptide by a covalent mode. Studies display that CPNs modified with anti-EpCAM can recognize MCF-7 tumor cells and locate on the membrane, while CPNs conjugated with transcriptional activator protein (Tat) specifically locate in the cytoplasm of MCF-7 cells. On the basis of the ability of CPNs for producing reactive oxygen species (ROS) under light irradiation, photodynamic therapy for tumor cells was investigated. Due to the long distance and wide diffusion range, MCF-7 tumor cells with CPNs/anti-EpCAM have no obvious change with or without white light irradiation. However, CPNs/Tat exhibits higher killing ability for MCF-7 cells. Noticeably, multifunctional CPNs linked with anti-EpCAM and Tat simultaneously not only can specifically target MCF-7 tumor cells, but also may inhibit and kill these cells. This work develops a potential application platform for multifunctional CPNs in locating imaging, photodynamic therapy, and other aspects.
ACS Appl Mater Interfaces 2016 Aug 03
PMID:Biological Functionalization of Conjugated Polymer Nanoparticles for Targeted Imaging and Photodynamic Killing of Tumor Cells. 2740 13

In this study, we fabricated conventional structured organic solar cells (OSCs) by introducing a hole extraction layer (HEL) that consisted of poly(3,4-ethylenedioxythiophene):polystyrenesulfonate (PEDOT:PSS) and conjugated polymer electrolyte (CPE) poly[9,9-bis(4'-sulfonatobutyl)fluorene-alt-thiophene] (PFT-D). PFT-D has a -SO3- functional group that acts as a conjugate base against the -SO3H of PSS. In addition, the molecular dipole of PFT-D can screen the Coulombic attraction between PEDOT chains and PSS chains. By blending PEDOT:PSS and PFT-D, the acidity of the HEL solution and changes to the surface morphology and potential of the HEL film as a function of exposure time in air were reduced. As a result, the half-life of the OSC fabricated with blended HEL was five times better at room temperature and 40% humidity without encapsulation as compared to the pristine PEDOT:PSS-based device.
ACS Appl Mater Interfaces 2016 Nov 23
PMID:Improvement in Half-Life of Organic Solar Cells by Using a Blended Hole Extraction Layer Consisting of PEDOT:PSS and Conjugated Polymer Electrolyte. 2776 50

In this study, we synthesized three conjugated polymer electrolytes (CPEs) with different conjugation lengths to control their dipole moments by varying spacers. P-type CPEs (PFT-D, PFtT-D, and PFbT-D) were generated by the facile oxidation of n-type CPEs (PFT, PFtT, and PFbT) and introduced as the hole-transporting layers (HTLs) of organic solar cells (OSCs) and polymer light-emitting diodes (PLEDs). To identify the effect on electrode work function tunability by changing the molecular conformation and arrangement, we simulated density functional theory calculations of these molecules and performed ultraviolet photoelectron spectroscopy analysis for films of indium tin oxide/CPEs. Additionally, we fabricated OSCs and PLEDs using the CPEs as the HTLs. The stability and performance were enhanced in the optimized devices with PFtT-D CPE HTLs compared to those of PEDOT:PSS HTL-based devices.
ACS Appl Mater Interfaces 2017 Dec 20
PMID:Effect on Electrode Work Function by Changing Molecular Geometry of Conjugated Polymer Electrolytes and Application for Hole-Transporting Layer of Organic Optoelectronic Devices. 2916 63