Selective recognition of biologically important anions using a diblock polyfluorene–polythiophene conjugated polyelectrolyte

Willis‐Fox, Niamh; Gutacker, Andrea; Browne, Michelle P.; Khan, Amir R.; Lyons, Michael E. G.; Scherf, Ullrich; Evans, Rachel C.

doi:10.1039/c7py01478c

Cited by 7 publications

(6 citation statements)

References 40 publications

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“…CPEs composed of conjugated backbone and side chains containing ionic groups are attractive materials due to their intrinsic dual electronic and ionic conductivity, and good solubility in polar solvents [ 351 , 352 , 353 , 354 , 355 , 356 ]. Some examples of the chemical structure of CPEs used as HTLs are shown in Scheme 2 .…”

Section: Hole-transporting Materials As Htls In Oscsmentioning

confidence: 99%

Recent Advances in Hole-Transporting Layers for Organic Solar Cells

et al. 2022

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Global energy demand is increasing; thus, emerging renewable energy sources, such as organic solar cells (OSCs), are fundamental to mitigate the negative effects of fuel consumption. Within OSC’s advancements, the development of efficient and stable interface materials is essential to achieve high performance, long-term stability, low costs, and broader applicability. Inorganic and nanocarbon-based materials show a suitable work function, tunable optical/electronic properties, stability to the presence of moisture, and facile solution processing, while organic conducting polymers and small molecules have some advantages such as fast and low-cost production, solution process, low energy payback time, light weight, and less adverse environmental impact, making them attractive as hole transporting layers (HTLs) for OSCs. This review looked at the recent progress in metal oxides, metal sulfides, nanocarbon materials, conducting polymers, and small organic molecules as HTLs in OSCs over the past five years. The endeavors in research and technology have optimized the preparation and deposition methods of HTLs. Strategies of doping, composite/hybrid formation, and modifications have also tuned the optical/electrical properties of these materials as HTLs to obtain efficient and stable OSCs. We highlighted the impact of structure, composition, and processing conditions of inorganic and organic materials as HTLs in conventional and inverted OSCs.

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Section: Hole-transporting Materials As Htls In Oscsmentioning

confidence: 99%

Recent Advances in Hole-Transporting Layers for Organic Solar Cells

et al. 2022

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“…Therefore, both experiments and molecular modeling indicate that guanidinium‐based π‐conjugated molecules could be utilized as organic chiroptical reporter for the detection of enzymatic activity, ie, hydrolysis by a phosphatase or phosphorylation by a kinase. This approach, coupled to conventional adenosine‐phosphates assays, could possibly help in the analysis of the composition in APs or other nucleotide phosphates, as recently reported for supramolecular polymers and conjugated copolymers . Moreover, the possibility of using guanidinium‐based photoresponsive molecules with GuaBiPy in multicomponent assemblies could also be exploited, for instance to modulate ATP release within dynamic supramolecular systems.…”

Section: Resultsmentioning

confidence: 99%

“…This approach, coupled to conventional adenosine-phosphates assays, could possibly help in the analysis of the composition in APs or other nucleotide phosphates, as recently reported for supramolecular polymers and conjugated copolymers. 1,11,33 Moreover, the possibility of using guanidinium-based photoresponsive molecules with GuaBiPy in multicomponent assemblies could also be exploited, 26 for instance to modulate ATP release within dynamic supramolecular systems.…”

Section: Discussionmentioning

confidence: 99%

Self‐assembly and chiroptical properties in supramolecular complexes of adenosine phosphates and guanidinium‐bispyrene

et al. 2018

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Supramolecular systems that respond to the hydrolysis of adenosine phosphates (APs) are attractive for biosensing and to fabricate bioinspired self-assembled materials. Here, we report on the formation of supramolecular complexes between an achiral guanidinium derivative bearing two pyrene moieties, with each of the three adenosine phosphates: AMP, ADP, and ATP. By combining results from circular dichroism spectroscopy and molecular modeling simulations, we explore the induced chirality, the dynamics of the complexes, and the interactions at play, which altogether provide insights into the supramolecular self-assembly between APs and the guanidinium-bispyrene. Finally, we identify the chiroptical signals of interest in mixtures of the guanidinium derivative with the three APs in different proportions. This study constitutes a basis to evolve toward a chiroptical detection of the hydrolysis of APs based on organic supramolecular probes.

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“…The aromaticity of the fluorene skeleton also makes the fluorenol derivative relatively highly acidic; the acid dissociation constants of the hydroxyl group and of the hydrogen atom at the 9‐position were reported to be 10.3 and 8.9, respectively, which are much larger than those of aliphatic alcohols and comparable to those of phenols . Polymers containing the 9‐substituted fluorene derivative unit have been synthesized as dyes and fluorescent materials for applications in organic solar cells and sensors, and these polymers are often substituted with bulky alkyl groups. However, the reports on the polymers containing fluorenol (alcohol) units had been very limited only to the two: the acetylenic polymer, poly(9‐ethynyl‐9‐fluorenol), and aromatic conjugated polymers containing the fluorenol unit …”

Section: Methodsmentioning

confidence: 99%

Reversible Hydrogen Releasing and Fixing with Poly(Vinylfluorenol) through a Mild Ir‐Catalyzed Dehydrogenation and Electrochemical Hydrogenation

Kato

Oka

Yoshimasa

et al. 2019

Macromol. Rapid Commun.

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The radical polymerization of 2‐vinylfluorenol, an alcohol derivative of vinylfluorene, gives poly(vinylfluorenol), which quantitatively releases hydrogen gas (≈110 mL per gram polymer at standard temperature and pressure) by simply warming at 100 °C with an iridium catalyst. A high population of fluorenol units in the polymer accomplishes a large formula‐weight‐based theoretical hydrogen density (1.0 wt%). The dehydrogenated ketone derivative, poly(vinylfluorenone), exhibits reversible negative‐charge storage with a high density of 260 mAh g−1. The electrolytically reduced poly(vinylfluorenone) is momentarily hydrogenated in the presence of an electrolyte with water as the hydrogen source to be converted to the original poly(vinylfluorenol). The formed poly(vinylfluorenol) almost quantitatively evolves hydrogen gas similar to the starting poly(vinylfluorenol). Both hydrogen and charge storage with the organic fluorenol/fluorenone polymer suggest a new type of energy‐storage configuration.

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Selective recognition of biologically important anions using a diblock polyfluorene–polythiophene conjugated polyelectrolyte

Abstract: Fluorescence detection of nucleotide phosphates with a polyfluorene–polythiophene diblock copolymer is demonstrated, accompanied by determination of the sensor mechanism.

Cited by 7 publications

References 40 publications

Recent Advances in Hole-Transporting Layers for Organic Solar Cells

Recent Advances in Hole-Transporting Layers for Organic Solar Cells

Self‐assembly and chiroptical properties in supramolecular complexes of adenosine phosphates and guanidinium‐bispyrene

Reversible Hydrogen Releasing and Fixing with Poly(Vinylfluorenol) through a Mild Ir‐Catalyzed Dehydrogenation and Electrochemical Hydrogenation

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