Abstract
Supramolecular chemistry allows the construction of complex molecular architectures and the design of collective photophysical properties. DNA is an attractive template to build such supramolecular architectures due to its helical structure, the defined distances between the bases and the canonical base pairing that results in precise control of the chromophore position. The tailored properties of DNA-templated supramolecules eventually allow their implementation into optoelectronic applications. For the generation of free charge carriers from photo-generated excitons, fullerenes can be utilized. We synthesized two fullerene derivates, one of which binds by electrostatic interactions to single-stranded DNA, while the other contains two 2′-deoxyuridine moieties and assembles specifically along oligo-2′-deoxyadenosines (dA20) as DNA template. The DNA-directed assembly of both fullerenes in aqueous solution was investigated by UV/Vis absorbance and circular dichroism (CD) spectroscopy. The specific interactions with DNA make fullerenes with the 2′-deoxyuridine moieties a significantly better component for supramolecular DNA architectures. We studied the fluorescence quenching of both fullerenes with a DNA chromophore assembly. To investigate one of the key properties for optoelectronic applications, that is the supramolecular structure of the DNA-based assemblies in the solid phase, we characterized the CD of supramolecular chromophore-DNA architectures in thin films. Remarkably, the helical chirality of the chromophore assemblies that is induced by the DNA template is conserved even in the solid state. Upon implementation into organic solar cells, the external quantum efficiency measurements showed charge carrier generation on all three chromophore components of the DNA assemblies. The fullerenes with the 2′-deoxyuridine moieties enhance the quantum efficiency of the conversion process significantly, demonstrating the potential of DNA as structural element for ordering chromophores into functional π-systems, which may be employed in future organic solar cells.
Highlights
Supramolecular chemistry enables the construction of complex molecular architectures and functional hybrids (Amabilino et al, 2017)
We report a new 2′-deoxyuridine conjugate fullerene 2 which we compare with a literatureknown fullerene 1 (Cassell et al, 1998) that both assemble along DNA templates (Figure 1) by two different types of interactions, as well as the spectroscopic investigation of the resulting DNA-based light harvesting systems with pyreneand nile red-nucleoside conjugates Py-≡-dU and Nr-≡-dU
We investigated whether the DNA-templated chromophore assembly prevailed the transition to the solid state upon thin film drying, eventually enabling their implementation as light-harvesting compounds in organic solar cells
Summary
Supramolecular chemistry enables the construction of complex molecular architectures and functional hybrids (Amabilino et al, 2017). The covalent conjugation of fullerene to the DNA template yielded a DNA-based light-harvesting system through the non-covalent assembly of pyrene and nile red dyes, which was used for the first time as an active layer in an organic solar cell (Ensslen et al, 2016). This showed that supramolecular DNA chromophore architectures are suitable for the use in optoelectronic applications. We investigated whether the DNA-templated chromophore assembly prevailed the transition to the solid state upon thin film drying, eventually enabling their implementation as light-harvesting compounds in organic solar cells
Sign-in/Register to view highlights & summary Sign-in/Register to access full text options 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
