Symmetry-Breaking Charge Separation in a Nanoscale Terrylenediimide Guanine-Quadruplex Assembly
Guanine-quadruplex (G-quadruplex) assemblies provide a useful platform for studying the spatial, structural, and photophysical effects of intermolecular interactions. Coupling a single guanine moiety to terrylenediimide (TDI)a chromophore with a large extended π-surfaceproduces a structure (GTDI)...
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| Published in | Journal of the American Chemical Society Vol. 141; no. 44; pp. 17512 - 17516 |
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| Main Authors | , , , |
| Format | Journal Article |
| Language | English |
| Published |
WASHINGTON
American Chemical Society
06.11.2019
Amer Chemical Soc American Chemical Society (ACS) |
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| Online Access | Get full text |
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| Abstract | Guanine-quadruplex (G-quadruplex) assemblies provide a useful platform for studying the spatial, structural, and photophysical effects of intermolecular interactions. Coupling a single guanine moiety to terrylenediimide (TDI)a chromophore with a large extended π-surfaceproduces a structure (GTDI) that assembles in plate-like tetramers, with the potential of undergoing tunable π-stacking. At high concentrations (3 × 10–3 M), GTDI self-assembles into a nearly monodisperse G-quadruplex structure of 16 layers, with strong π-overlap between TDI moieties, observed by small- and wide-angle X-ray scattering. Transient absorption spectroscopy reveals that excitation of TDI in the G-quadruplex results in symmetry-breaking charge separation to form ion pairs within the structure, owing to the strong π-overlap enforced by the hydrogen-bonding. These assemblies yield important insights into the interplay of noncovalent interactions in the assembly of ordered chromophoric arrays. |
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| AbstractList | Guanine-quadruplex (G-quadruplex) assemblies provide a useful platform for studying the spatial, structural, and photophysical effects of intermolecular interactions. Coupling a single guanine moiety to terrylenediimide (TDI)a chromophore with a large extended π-surfaceproduces a structure (GTDI) that assembles in plate-like tetramers, with the potential of undergoing tunable π-stacking. At high concentrations (3 × 10–3 M), GTDI self-assembles into a nearly monodisperse G-quadruplex structure of 16 layers, with strong π-overlap between TDI moieties, observed by small- and wide-angle X-ray scattering. Transient absorption spectroscopy reveals that excitation of TDI in the G-quadruplex results in symmetry-breaking charge separation to form ion pairs within the structure, owing to the strong π-overlap enforced by the hydrogen-bonding. These assemblies yield important insights into the interplay of noncovalent interactions in the assembly of ordered chromophoric arrays. Guanine-quadruplex (G-quadruplex) assemblies provide a useful platform for studying the spatial, structural, and photophysical effects of intermolecular interactions. Coupling a single guanine moiety to terrylenediimide (TDI)—a chromophore with a large extended π-surface—produces a structure (GTDI) that assembles in plate-like tetramers, with the potential of undergoing tunable π-stacking. At high concentrations (3 × 10–³ M), GTDI self-assembles into a nearly monodisperse G-quadruplex structure of 16 layers, with strong π-overlap between TDI moieties, observed by small- and wide-angle X-ray scattering. Transient absorption spectroscopy reveals that excitation of TDI in the G-quadruplex results in symmetry-breaking charge separation to form ion pairs within the structure, owing to the strong π-overlap enforced by the hydrogen-bonding. These assemblies yield important insights into the interplay of noncovalent interactions in the assembly of ordered chromophoric arrays. Guanine-quadruplex (G-quadruplex) assemblies provide a useful platform for studying the spatial, structural, and photophysical effects of intermolecular interactions. Coupling a single guanine moiety to terrylenediimide (TDI)-a chromophore with a large extended π-surface-produces a structure (GTDI) that assembles in plate-like tetramers, with the potential of undergoing tunable π-stacking. At high concentrations (3 × 10-3 M), GTDI self-assembles into a nearly monodisperse G-quadruplex structure of 16 layers, with strong π-overlap between TDI moieties, observed by small- and wide-angle X-ray scattering. Transient absorption spectroscopy reveals that excitation of TDI in the G-quadruplex results in symmetry-breaking charge separation to form ion pairs within the structure, owing to the strong π-overlap enforced by the hydrogen-bonding. These assemblies yield important insights into the interplay of noncovalent interactions in the assembly of ordered chromophoric arrays.Guanine-quadruplex (G-quadruplex) assemblies provide a useful platform for studying the spatial, structural, and photophysical effects of intermolecular interactions. Coupling a single guanine moiety to terrylenediimide (TDI)-a chromophore with a large extended π-surface-produces a structure (GTDI) that assembles in plate-like tetramers, with the potential of undergoing tunable π-stacking. At high concentrations (3 × 10-3 M), GTDI self-assembles into a nearly monodisperse G-quadruplex structure of 16 layers, with strong π-overlap between TDI moieties, observed by small- and wide-angle X-ray scattering. Transient absorption spectroscopy reveals that excitation of TDI in the G-quadruplex results in symmetry-breaking charge separation to form ion pairs within the structure, owing to the strong π-overlap enforced by the hydrogen-bonding. These assemblies yield important insights into the interplay of noncovalent interactions in the assembly of ordered chromophoric arrays. Guanine-quadruplex (G-quadruplex) assemblies provide a useful platform for studying the spatial, structural, and photophysical effects of intermolecular interactions. Coupling a single guanine moiety to terrylenediimide (TDI)-a chromophore with a large extended π-surface-produces a structure ( ) that assembles in plate-like tetramers, with the potential of undergoing tunable π-stacking. At high concentrations (3 × 10 M), self-assembles into a nearly monodisperse G-quadruplex structure of 16 layers, with strong π-overlap between TDI moieties, observed by small- and wide-angle X-ray scattering. Transient absorption spectroscopy reveals that excitation of TDI in the G-quadruplex results in symmetry-breaking charge separation to form ion pairs within the structure, owing to the strong π-overlap enforced by the hydrogen-bonding. These assemblies yield important insights into the interplay of noncovalent interactions in the assembly of ordered chromophoric arrays. Guanine-quadruplex (G-quadruplex) assemblies provide a useful platform for studying the spatial, structural, and photophysical effects of intermolecular interactions. Coupling a single guanine moiety to terrylenediimide (TDI)—a chromophore with a large extended $π$-surface—produces a structure (GTDI) that assembles in plate-like tetramers, with the potential of undergoing tunable $π$-stacking. We report that at high concentrations (3 x 10-3 M), GTDI self-assembles into a nearly monodisperse G-quadruplex structure of 16 layers, with strong $π$-overlap between TDI moieties, observed by small- and wide-angle X-ray scattering. Transient absorption spectroscopy reveals that excitation of TDI in the G-quadruplex results in symmetry-breaking charge separation to form ion pairs within the structure, owing to the strong $π$-overlap enforced by the hydrogen-bonding. These assemblies yield important insights into the interplay of noncovalent interactions in the assembly of ordered chromophoric arrays. Guanine-quadruplex (G-quadruplex) assemblies provide a useful platform for studying the spatial, structural, and photophysical effects of intermolecular interactions. Coupling a single guanine moiety to terrylenediimide (TDI)-a chromophore with a large extended pi-surface-produces a structure (GTDI) that assembles in plate-like tetramers, with the potential of undergoing tunable pi-stacking. At high concentrations (3 x 10(-3) M), GTDI self-assembles into a nearly monodisperse G-quadruplex structure of 16 layers, with strong p-overlap between TDI moieties, observed by small- and wide-angle X-ray scattering. Transient absorption spectroscopy reveals that excitation of TDI in the G-quadruplex results in symmetry-breaking charge separation to form ion pairs within the structure, owing to the strong pi-overlap enforced by the hydrogen-bonding. These assemblies yield important insights into the interplay of noncovalent interactions in the assembly of ordered chromophoric arrays. |
| Author | Powers-Riggs, Natalia E Zuo, Xiaobing Wasielewski, Michael R Young, Ryan M |
| AuthorAffiliation | Department of Chemistry and Institute for Sustainability and Energy at Northwestern X-ray Science Division |
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| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/31647646$$D View this record in MEDLINE/PubMed https://www.osti.gov/servlets/purl/1608330$$D View this record in Osti.gov |
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| Keywords | X-RAY SOLUTION BIOLOGICAL MACROMOLECULES DNA SOLUTION SCATTERING G-QUARTETS SINGLET FISSION CATION PERYLENE |
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| Snippet | Guanine-quadruplex (G-quadruplex) assemblies provide a useful platform for studying the spatial, structural, and photophysical effects of intermolecular... |
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| SubjectTerms | Absorption Chemical structure Chemistry Chemistry, Multidisciplinary G-Quadruplex Guanine hydrogen bonding INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY moieties Physical Sciences Scattering Science & Technology spectroscopy wide-angle X-ray scattering |
| Title | Symmetry-Breaking Charge Separation in a Nanoscale Terrylenediimide Guanine-Quadruplex Assembly |
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