Mixed non-covalent assemblies of ethynyl nile red and ethynyl pyrene along oligonucleotide templates

Ensslen, Philipp; Fritz, Yannic; Wagenknecht, Hans‐Achim

doi:10.1039/c4ob01860e

Cited by 31 publications

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“…Theonly difference to the covalent systems [7] was the left-handed chirality of the noncovalent chromophore assemblies.M ixed assemblies of Py--dU and the ethynyl-Nile-red-modified nucleoside (Nr--dU) along (dA) 20 yielded dual emission as ar esult of energy transfer between the two different chromophores. [8] To develop al ight-harvesting system from these assemblies for future DNA-based solar cells,w ep resent herein the templated assembly of the two chromophore conjugates Py--dU and Nr--dU along (dA) 20 as as ynthetic oligonucleotide, which has previously been conjugated to af ullerene,a nd its optical and photovoltaic properties. We have previously studied the photophysical processes between Py--dU and Nr--dU in DNAd ouble strands that were covalently modified with these two chromophores in close proximity to each other.…”

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A DNA–Fullerene Conjugate as a Template for Supramolecular Chromophore Assemblies: Towards DNA‐Based Solar Cells

et al. 2015

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A fullerene was covalently attached to a (dA)20 template that serves as structural scaffold to self-assemble an ordered and mixed array of ethynyl-pyrene- and ethynyl-Nile-red-nucleoside conjugates. Fluorescence spectroscopy revealed evidence for energy transfer between the two different chromophores. Moreover, fluorescence quenching is significantly enhanced by the attached fullerene in mixed assemblies of different chromophore ratios. This indicates exciton dissociation by electron transfer from the photo-generated exciton on the chromophore stack to the fullerene. The fullerene-DNA-conjugate was integrated as a photo-active layer in solar cells that showed charge-carrier generation in the spectral regime of all three components of the conjugate. This work clearly demonstrates that DNA is suitable as structural element for chromophore assemblies in future organic optoelectronic devices, such as solar cells.

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A DNA–Fullerene Conjugate as a Template for Supramolecular Chromophore Assemblies: Towards DNA‐Based Solar Cells

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“…[8] Die Fluoreszenzlçschung in den Chromophoraggregaten entlang des unmodifizierten (dA) 20 Te mplats kann durch einen Energietransfer von Py--dU auf Nr--dU gefolgt von einem Ladungstransfer in entgegengesetzter Richtung erklärt werden, der zu einem ladungsgetrennten Zustand (Exciton) führt. [9] Die Fluoreszenintensitäten beider Chromophore,Py--dU bei 475 nm und Nr--dU bei 672 nm, sind in Gegenwart des angehängten Fullerens noch stärker gelçscht (Abbildung 1, unten), insbesondere in solch verdünnten Lçsungen (Konzentration des Te mplats 1 mm).…”

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“…Der einzige Unterschied zu den kovalenten Systemen [7] ist die linksgängige Chiralität der nichtkovalenten Chromophor-Aggregate.G emischte Stapel von Py--dU und Ethinylnilrot-modifizierten Nucleosiden (Nr--dU) entlang (dA) 20 erzeugten eine duale Emission durch den Energietransfer zwischen den beiden Chromophoren. [8] Um aus diesen Aggregaten Lichtsammelsysteme für zukünftige DNA-basierte Solarzellen zu entwickeln, präsentieren wir hier die templierte Assoziation der beiden ChromophorKonjugate Py--dU und Nr--dU entlang (dA) 20 als Oligonucleotid, das zuvor mit einem Fulleren synthetisch konjugiert wurden, sowie die optischen und photoelektrischen Eigenschaften.…”

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“…[6,8] Die Chromophor-NucleosidKonjugate bilden p-Stapel, deren Spezifität vermutlich von Wasserstoffbrücken ähnlich der Watson-Crick-Basenpaarung herrührt. Außerdem haben wir gezeigt, dass Te mplate mit der Länge (dA) 10 -(dA) 20 fast exakt so viele Nr--dU-Monomere binden, wie sie Bindungsstellen enthalten.…”

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“…Außerdem haben wir gezeigt, dass Te mplate mit der Länge (dA) 10 -(dA) 20 fast exakt so viele Nr--dU-Monomere binden, wie sie Bindungsstellen enthalten. [8] Für die hier berichtete Arbeit verlassen wir uns auf diese Eigenschaften, Schema 1. Photophysikalisches Prinzip des Chromophorpaars Py--dU und Nr--dU in DNA: [9] Nach selektiver Anregungv on Py--dU erfolgt ein Energietransfer von Py--dU auf Nr--dU, gefolgt von einem Ladungstransfer in entgegengesetzter Richtung, von Nr--dU auf Py--dU, der zu einem ladungsgetrennten Zustand führt.…”

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Ein DNA‐Fulleren‐Konjugat als Templat für supramolekulare Chromophorstapel: Auf dem Weg zu DNA‐basierten Solarzellen

et al. 2015

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Merging Biology and Photovoltaics: How Nature Helps Sun‐Catching

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et al. 2021

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conditions. This makes difficult to further reduce the cost of electricity production. [7,8] Furthermore, although solar energy is a renewable source, it does not mean that any kind of photovoltaics (PV) is sustainable. For instance, silicon is an essential material in electronics and solar industries and, up to date, is irreplaceable. Despite its abundancy in Earth's crust, it is for the vast majority (80%) present as ferrosilicon, whose purification is expensive and highly pollutant. The production of 1 ton of silicon requires 6 tons of raw materials, almost 3 tons of Quartz, 1.5 tons of reducing agents, 1.5 tons of wood and 13 000 kWh of energy. [9,10] Therefore, in 2014 the EU commission included silicon metal in the critical raw material (CRM) list. [11] In this context, the third generation PV has reborn, offering cost-effective and efficient CRM-free devices with a lower reliance on the incident angle of light and integration in smart-end applications, like flexible and wearable devices, [12][13][14] fully transparent solar cells and windows, [15,16] and biocompatible devices. [17][18][19] The leading third generation SCs are organic solar cells (OSCs), [20][21][22] perovskite solar cells (PSCs), [23][24][25][26][27] and dye-sensitized solar cells (DSSCs). [28][29][30] Despite their versatile applications and high performances, sustainability still represents a major issue toward becoming an ideal energy technology in the mid-long term future. Among others, fullerene-based materials are toxic, [31] indium tin oxide (ITO) is brittle, chemically unstable, and expensive due to limited indium sources on Earth's crust. [32,33] Cobalt is also listed as CRM, [11] while cadmium, selenium, lead and ruthenium are toxic materials. [34,35] With regard to flexible devices, polyethylene terephthalate (PET) is the standard substrate; though its environmental footprint is critical and its nonbiodegradable properties lead to harmful effects in living organisms. [36] This has fueled a strong cooperation among the fields of engineering, biology, chemistry, and physics to discover new strategies for cost-effectiveness preparation and implementation of bio-derived materials in highly performing PVs.In general, this cooperation constitutes a part of the emerging and multidisciplinary field of biophotonics, [37] which involves biomedical optics, [38] living light, [39][40][41] biomimetic, biomaterials and bioengineered compounds, as well as fabrication/implementation methods applied to optoelectronics [42] and photonics, [43] among others. For instance, artificial lightning and biology have been recently merged with the implementation of cellulose, chitosan, silk, and fluorescent proteins as Accomplishing sustainability in optoelectronics, in general, and photovoltaics (PV), in particular, represents a crucial milestone in green photonics. Third generation PV technologies, such as organic solar cells (OSCs), perovskite solar cells (PSCs), and dye-sensitized solar cells (DSSCs) have reached a mature age and are slowly making thei...

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Mixed non-covalent assemblies of ethynyl nile red and ethynyl pyrene along oligonucleotide templates

Cited by 31 publications

References 30 publications

A DNA–Fullerene Conjugate as a Template for Supramolecular Chromophore Assemblies: Towards DNA‐Based Solar Cells

A DNA–Fullerene Conjugate as a Template for Supramolecular Chromophore Assemblies: Towards DNA‐Based Solar Cells

Ein DNA‐Fulleren‐Konjugat als Templat für supramolekulare Chromophorstapel: Auf dem Weg zu DNA‐basierten Solarzellen

Merging Biology and Photovoltaics: How Nature Helps Sun‐Catching

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