Kole, Goutam Kumar; Košćak, Marta; Amar, Anissa; Majhen, Dragomira; Božinović, Ksenija; Brkljača, Zlatko; Ferger, Matthias; Michail, Evripidis; Lorenzen, Sabine; Friedrich, Alexandra; Krummenacher, Ivo; Moos, Michael; Braunschweig, Holger; Boucekkine, Abdou; Lambert, Christoph; Halet, Jean-François; Piantanida, Ivo; Müller-Buschbaum, Klaus; Marder, Todd B. (2022) Methyl Viologens of Bis-(4'-pyridylethynyl)arenes - Structures, Photophysical and Electrochemical Studies, and their Potential Application in Biology. Chemistry : a European journal, 28 (40). ISSN 0947-6539
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Abstract
A series of bis-(4'-pyridylethynyl)arenes (arene = benzene, tetrafluorobenzene, and anthracene) were synthesized and their bis-N-methylpyridinium compounds were investigated as a class of π-extended methyl viologens. Their structures were determined by single crystal X-ray diffraction, and their photophysical and electrochemical properties (cyclic voltammetry), as well as their interactions with DNA/RNA were investigated. The dications showed bathochromic shifts in emission compared to the neutral compounds. The neutral compounds showed very small Stokes shifts, which are a little larger for the dications. All of the compounds showed very short fluorescence lifetimes (< 4 ns). The neutral compound with an anthracene core has a quantum yield of almost unity. With stronger acceptors, the analogous bis-N-methylpyridinium compound showed a larger two-photon absorption cross-section than its neutral precursor. All of the dicationic compounds interact with DNA/RNA ; while the compounds with benzene and tetrafluorobenzene cores bind in the grooves, the one with an anthracene core intercalates as a consequence of its large, condensed aromatic linker moiety, and it aggregates within the polynucleotide when in excess over DNA/RNA.
| Item Type: | Article | ||||||||
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| Uncontrolled Keywords: | Methyl Viologen ; Two-photon Absorption ; Singlet Oxygen ; DNA/RNA Binding ; Cell Imaging | ||||||||
| Subjects: | NATURAL SCIENCES > Chemistry NATURAL SCIENCES > Biology |
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| Divisions: | Division of Molecular Biology Division of Organic Chemistry and Biochemistry |
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| Depositing User: | Sofija Konjević | ||||||||
| Date Deposited: | 02 Aug 2022 06:41 | ||||||||
| URI: | http://fulir.irb.hr/id/eprint/7503 | ||||||||
| DOI: | 10.1002/chem.202200753 |
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