Methyl Viologens of Bis-(4'-pyridylethynyl)arenes - Structures, Photophysical and Electrochemical Studies, and their Potential Application in Biology

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.

doi:10.1002/chem.202200753

Pregled bibliografske jedinice broj: 1192656

Methyl Viologens of Bis-(4'-pyridylethynyl)arenes - Structures, Photophysical and Electrochemical Studies, and their Potential Application in Biology

Kole, Goutam Kumar; Košćak, Marta; Amar, Anissa; Majhen, Dragomira; Božinović, Ksenija; Brkljača, Zlatko; Ferger, Matthias; Michail, Evripidis; Lorenzen, Sabine; Friedrich, Alexandra et al.

Methyl Viologens of Bis-(4'-pyridylethynyl)arenes - Structures, Photophysical and Electrochemical Studies, and their Potential Application in Biology // Chemistry : a European journal, 28 (2022), 40; e202200753, 22 doi:10.1002/chem.202200753 (međunarodna recenzija, članak, znanstveni)

CROSBI ID: 1192656 Za ispravke kontaktirajte CROSBI podršku putem web obrasca

Naslov
Methyl Viologens of Bis-(4'-pyridylethynyl)arenes - Structures, Photophysical and Electrochemical Studies, and their Potential Application in Biology

Autori
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.

Izvornik
Chemistry : a European journal (0947-6539) 28 (2022), 40; E202200753, 22

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
Methyl Viologen ; Two-photon Absorption ; Singlet Oxygen ; DNA/RNA Binding ; Cell Imaging

Sažetak
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.

Izvorni jezik
Engleski

Znanstvena područja
Kemija, Biologija

POVEZANOST RADA

Projekti:
HRZZ-IP-2018-01-5475 - Višekromoforne probe za prepoznavanje pojedinih struktura DNA, RNA i proteina (BioMultiChromoProbes) (Piantanida, Ivo, HRZZ - 2018-01) ( CroRIS)

Ustanove:
Institut "Ruđer Bošković", Zagreb

Profili:

Ivo Piantanida (autor)