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2- and 2,7-substituted para-N-methylpyridinium pyrenes: syntheses, molecular and electronic structures, photophysical, electrochemical, and spectroelectrochemical properties and binding to double-stranded (ds) DNA
Zitieren Sie bitte immer diese URN: urn:nbn:de:bvb:20-opus-256642
- Two N-methylpyridinium compounds and analogous N-protonated salts of 2- and 2,7-substituted 4-pyridyl-pyrene compounds were synthesised and their crystal structures, photophysical properties both in solution and in the solid state, electrochemical and spectroelectrochemical properties were studied. Upon methylation or protonation, the emission maxima are significantly bathochromically shifted compared to the neutral compounds, although the absorption maxima remain almost unchanged. As a result, the cationic compounds show very large apparentTwo N-methylpyridinium compounds and analogous N-protonated salts of 2- and 2,7-substituted 4-pyridyl-pyrene compounds were synthesised and their crystal structures, photophysical properties both in solution and in the solid state, electrochemical and spectroelectrochemical properties were studied. Upon methylation or protonation, the emission maxima are significantly bathochromically shifted compared to the neutral compounds, although the absorption maxima remain almost unchanged. As a result, the cationic compounds show very large apparent Stokes shifts of up to 7200 cm\(^{-1}\). The N-methylpyridinium compounds have a single reduction at ca. −1.5 V vs. Fc/Fc\(^+\) in MeCN. While the reduction process was reversible for the 2,7-disubstituted compound, it was irreversible for the mono-substituted one. Experimental findings are complemented by DFT and TD-DFT calculations. Furthermore, the N-methylpyridinium compounds show strong interactions with calf thymus (ct)-DNA, presumably by intercalation, which paves the way for further applications of these multi-functional compounds as potential DNA-bioactive agents.…
Autor(en): | Goutam Kumar Kole, Julia Merz, Anissa Amar, Bruno Fontaine, Abdou Boucekkine, Jörn Nitsch, Sabine Lorenzen, Alexandra Friedrich, Ivo Krummenacher, Marta Košćak, Holger BraunschweigORCiD, Ivo Piantanida, Jean-François Halet, Klaus Müller-Buschbaum, Todd B. MarderORCiD |
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URN: | urn:nbn:de:bvb:20-opus-256642 |
Dokumentart: | Artikel / Aufsatz in einer Zeitschrift |
Institute der Universität: | Fakultät für Chemie und Pharmazie / Institut für Anorganische Chemie |
Sprache der Veröffentlichung: | Englisch |
Titel des übergeordneten Werkes / der Zeitschrift (Englisch): | Chemistry - A European Journal |
Erscheinungsjahr: | 2021 |
Band / Jahrgang: | 27 |
Heft / Ausgabe: | 8 |
Seitenangabe: | 2837–2853 |
Originalveröffentlichung / Quelle: | Chemistry - A European Journal (2021) 27:8, 2837–2853. DOI: 10.1002/chem.202004748 |
DOI: | https://doi.org/10.1002/chem.202004748 |
Allgemeine fachliche Zuordnung (DDC-Klassifikation): | 5 Naturwissenschaften und Mathematik / 54 Chemie / 546 Anorganische Chemie |
Freie Schlagwort(e): | chromophores; inorganic chemistry; luminescent; pyrenes; pyridinium; viologens |
Datum der Freischaltung: | 25.02.2022 |
Lizenz (Deutsch): | CC BY: Creative-Commons-Lizenz: Namensnennung 4.0 International |