Methyl Viologens of Bis‐(4’‐Pyridylethynyl)Arenes – Structures, Photophysical and Electrochemical Studies, and their Potential Application in Biology
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 photo...
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| Published in | Chemistry : a European journal Vol. 28; no. 40; pp. e202200753 - n/a |
|---|---|
| Main Authors | , , , , , , , , , , , , , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
WEINHEIM
Wiley
15.07.2022
Wiley Subscription Services, Inc Wiley-VCH Verlag John Wiley and Sons Inc |
| Subjects | |
| Online Access | Get full text |
| ISSN | 0947-6539 1521-3765 1521-3765 |
| DOI | 10.1002/chem.202200753 |
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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. Moreover, all cationic compounds showed highly specific CD spectra upon binding to ds‐DNA/RNA, attributed to the rare case of forcing the planar, achiral molecule into a chiral rotamer, and negligible toxicity toward human cell lines at ≤10 μM concentrations. The anthracene‐analogue exhibited intracellular accumulation within lysosomes, preventing its interaction with cellular DNA/RNA. However, cytotoxicity was evident at 1 μM concentration upon exposure to light, due to singlet oxygen generation within cells. These multi‐faceted features, in combination with its two‐photon absorption properties, suggest it to be a promising lead compound for development of novel light‐activated theranostic agents.
Methyl‐viologens containing π‐extended bis(N‐methylpyridiniumethynyl)arenes (arene=benzene, tetrafluorobenzene, anthracene) were crystallographically characterized and their electrochemical properties and one‐ and two‐photon absorption and fluorescence spectra were measured. With DNA/RNA, while the benzene and tetrafluorobenzene analogues bind in grooves, the anthracene analogue intercalates due to its large aromatic moiety, and aggregates within the polynucleotide when in excess over DNA/RNA. The latter compound localizes within lysosomes, preventing its interaction with cellular DNA/RNA, but exhibited cytotoxicity upon photoexcitation, due to 1O2 generation within cells. |
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| AbstractList | 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. Moreover, all cationic compounds showed highly specific CD spectra upon binding to ds-DNA/RNA, attributed to the rare case of forcing the planar, achiral molecule into a chiral rotamer, and negligible toxicity toward human cell lines at ≤10 μM concentrations. The anthracene-analogue exhibited intracellular accumulation within lysosomes, preventing its interaction with cellular DNA/RNA. However, cytotoxicity was evident at 1 μM concentration upon exposure to light, due to singlet oxygen generation within cells. These multi-faceted features, in combination with its two-photon absorption properties, suggest it to be a promising lead compound for development of novel light-activated theranostic agents. 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. Moreover, all cationic compounds showed highly specific CD spectra upon binding to ds‐DNA/RNA, attributed to the rare case of forcing the planar, achiral molecule into a chiral rotamer, and negligible toxicity toward human cell lines at ≤10 μM concentrations. The anthracene‐analogue exhibited intracellular accumulation within lysosomes, preventing its interaction with cellular DNA/RNA. However, cytotoxicity was evident at 1 μM concentration upon exposure to light, due to singlet oxygen generation within cells. These multi‐faceted features, in combination with its two‐photon absorption properties, suggest it to be a promising lead compound for development of novel light‐activated theranostic agents. 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 pi-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. Moreover, all cationic compounds showed highly specific CD spectra upon binding to ds-DNA/RNA, attributed to the rare case of forcing the planar, achiral molecule into a chiral rotamer, and negligible toxicity toward human cell lines at <= 10 mu M concentrations. The anthracene-analogue exhibited intracellular accumulation within lysosomes, preventing its interaction with cellular DNA/RNA. However, cytotoxicity was evident at 1 mu M concentration upon exposure to light, due to singlet oxygen generation within cells. These multi-faceted features, in combination with its two-photon absorption properties, suggest it to be a promising lead compound for development of novel light-activated theranostic agents. 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. Moreover, all cationic compounds showed highly specific CD spectra upon binding to ds‐DNA/RNA, attributed to the rare case of forcing the planar, achiral molecule into a chiral rotamer, and negligible toxicity toward human cell lines at ≤10 μM concentrations. The anthracene‐analogue exhibited intracellular accumulation within lysosomes, preventing its interaction with cellular DNA/RNA. However, cytotoxicity was evident at 1 μM concentration upon exposure to light, due to singlet oxygen generation within cells. These multi‐faceted features, in combination with its two‐photon absorption properties, suggest it to be a promising lead compound for development of novel light‐activated theranostic agents. Methyl‐viologens containing π‐extended bis(N‐methylpyridiniumethynyl)arenes (arene=benzene, tetrafluorobenzene, anthracene) were crystallographically characterized and their electrochemical properties and one‐ and two‐photon absorption and fluorescence spectra were measured. With DNA/RNA, while the benzene and tetrafluorobenzene analogues bind in grooves, the anthracene analogue intercalates due to its large aromatic moiety, and aggregates within the polynucleotide when in excess over DNA/RNA. The latter compound localizes within lysosomes, preventing its interaction with cellular DNA/RNA, but exhibited cytotoxicity upon photoexcitation, due to 1O2 generation within cells. 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. Moreover, all cationic compounds showed highly specific CD spectra upon binding to ds‐DNA/RNA, attributed to the rare case of forcing the planar, achiral molecule into a chiral rotamer, and negligible toxicity toward human cell lines at ≤10 μM concentrations. The anthracene‐analogue exhibited intracellular accumulation within lysosomes, preventing its interaction with cellular DNA/RNA. However, cytotoxicity was evident at 1 μM concentration upon exposure to light, due to singlet oxygen generation within cells. These multi‐faceted features, in combination with its two‐photon absorption properties, suggest it to be a promising lead compound for development of novel light‐activated theranostic agents.In memory of Prof. Em. Dr. Dr. h.c. mult. Siegfried Hünig. 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. Moreover, all cationic compounds showed highly specific CD spectra upon binding to ds-DNA/RNA, attributed to the rare case of forcing the planar, achiral molecule into a chiral rotamer, and negligible toxicity toward human cell lines at ≤10 μM concentrations. The anthracene-analogue exhibited intracellular accumulation within lysosomes, preventing its interaction with cellular DNA/RNA. However, cytotoxicity was evident at 1 μM concentration upon exposure to light, due to singlet oxygen generation within cells. These multi-faceted features, in combination with its two-photon absorption properties, suggest it to be a promising lead compound for development of novel light-activated theranostic agents.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. Moreover, all cationic compounds showed highly specific CD spectra upon binding to ds-DNA/RNA, attributed to the rare case of forcing the planar, achiral molecule into a chiral rotamer, and negligible toxicity toward human cell lines at ≤10 μM concentrations. The anthracene-analogue exhibited intracellular accumulation within lysosomes, preventing its interaction with cellular DNA/RNA. However, cytotoxicity was evident at 1 μM concentration upon exposure to light, due to singlet oxygen generation within cells. These multi-faceted features, in combination with its two-photon absorption properties, suggest it to be a promising lead compound for development of novel light-activated theranostic agents. 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 X-ray diffraction, and their photophysical and electrochemical properties 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. 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 dicationic compound showed a larger 2-photon absorption (TPA) 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, aromatic linker moiety, and it aggregates within the polynucleotide when in excess over DNA/RNA. All cationic compounds showed highly specific CD spectra upon binding to ds-DNA/RNA, attributed to the rare case of forcing the planar, achiral molecule into a chiral rotamer, and negligible toxicity toward human cell lines at ≤ 10 µM concentrations. The anthracene-analogue exhibited intracellular accumulation within lysosomes, preventing its interaction with cellular DNA/RNA. However, cytotoxicity was evident at 1 µM concentration upon exposure to light, due to singlet oxygen generation within cells. These features, in combination with its TPA properties, suggest it to be a promising lead compound for development of light-activated theranostic agents. |
| ArticleNumber | 202200753 |
| Author | Krummenacher, Ivo Majhen, Dragomira Braunschweig, Holger Lambert, Christoph Božinović, Ksenija Friedrich, Alexandra Brkljaca, Zlatko Halet, Jean‐François Marder, Todd B. Michail, Evripidis Müller‐Buschbaum, Klaus Piantanida, Ivo Kole, Goutam Kumar Boucekkine, Abdou Lorenzen, Sabine Košćak, Marta Amar, Anissa Ferger, Matthias Moos, Michael |
| AuthorAffiliation | 7 CNRS-Saint-Gobain-NIMS IRL 3629 Laboratory for Innovative Key Materials and Structures (LINK) National Institute for Materials Science (NIMS) Tsukuba 305-0044 Japan 1 Institut für Anorganische Chemie, and Institute for Sustainable Chemistry & Catalysis with Boron Julius-Maximilians-Universität Würzburg Am Hubland 97074 Würzburg Germany 8 Institut für Anorganische und Analytische Chemie Justus-Liebig-Universität Gießen Heinrich-Buff-Ring 17 35392 Gießen Germany 2 Department of Chemistry College of Engineering and Technology SRM Institute of Science and Technology, SRM Nagar Kattankulathur Tamil Nadu 603203 India 3 Ruđer Bošković Institute 10000 Zagreb Croatia 4 Laboratoire de Physique et Chimie Quantiques Université Mouloud Mammeri Tizi Ouzou 15000 Tizi-Ouzou Algeria 5 Institut für Organische Chemie Julius-Maximilians-Universität Würzburg Am Hubland 97074 Würzburg Germany 6 Univ Rennes, Ecole Nationale Supérieure de Chimie de Rennes, CNRS, Institut des Sciences Chimiques de Rennes UMR 6226 3 |
| AuthorAffiliation_xml | – name: 6 Univ Rennes, Ecole Nationale Supérieure de Chimie de Rennes, CNRS, Institut des Sciences Chimiques de Rennes UMR 6226 35000 Rennes France – name: 5 Institut für Organische Chemie Julius-Maximilians-Universität Würzburg Am Hubland 97074 Würzburg Germany – name: 8 Institut für Anorganische und Analytische Chemie Justus-Liebig-Universität Gießen Heinrich-Buff-Ring 17 35392 Gießen Germany – name: 3 Ruđer Bošković Institute 10000 Zagreb Croatia – name: 7 CNRS-Saint-Gobain-NIMS IRL 3629 Laboratory for Innovative Key Materials and Structures (LINK) National Institute for Materials Science (NIMS) Tsukuba 305-0044 Japan – name: 2 Department of Chemistry College of Engineering and Technology SRM Institute of Science and Technology, SRM Nagar Kattankulathur Tamil Nadu 603203 India – name: 1 Institut für Anorganische Chemie, and Institute for Sustainable Chemistry & Catalysis with Boron Julius-Maximilians-Universität Würzburg Am Hubland 97074 Würzburg Germany – name: 4 Laboratoire de Physique et Chimie Quantiques Université Mouloud Mammeri Tizi Ouzou 15000 Tizi-Ouzou Algeria |
| Author_xml | – sequence: 1 givenname: Goutam Kumar orcidid: 0000-0002-1503-0574 surname: Kole fullname: Kole, Goutam Kumar organization: SRM Institute of Science and Technology, SRM Nagar – sequence: 2 givenname: Marta surname: Košćak fullname: Košćak, Marta organization: Ruđer Bošković Institute – sequence: 3 givenname: Anissa orcidid: 0000-0002-1365-915X surname: Amar fullname: Amar, Anissa organization: Université Mouloud Mammeri – sequence: 4 givenname: Dragomira orcidid: 0000-0003-0385-0900 surname: Majhen fullname: Majhen, Dragomira organization: Ruđer Bošković Institute – sequence: 5 givenname: Ksenija orcidid: 0000-0001-6840-6689 surname: Božinović fullname: Božinović, Ksenija organization: Ruđer Bošković Institute – sequence: 6 givenname: Zlatko surname: Brkljaca fullname: Brkljaca, Zlatko organization: Ruđer Bošković Institute – sequence: 7 givenname: Matthias orcidid: 0000-0001-9280-0619 surname: Ferger fullname: Ferger, Matthias organization: Julius-Maximilians-Universität Würzburg – sequence: 8 givenname: Evripidis surname: Michail fullname: Michail, Evripidis organization: Julius-Maximilians-Universität Würzburg – sequence: 9 givenname: Sabine surname: Lorenzen fullname: Lorenzen, Sabine organization: Julius-Maximilians-Universität Würzburg – sequence: 10 givenname: Alexandra orcidid: 0000-0002-1411-7336 surname: Friedrich fullname: Friedrich, Alexandra organization: Julius-Maximilians-Universität Würzburg – sequence: 11 givenname: Ivo orcidid: 0000-0001-9537-1506 surname: Krummenacher fullname: Krummenacher, Ivo organization: Julius-Maximilians-Universität Würzburg – sequence: 12 givenname: Michael surname: Moos fullname: Moos, Michael organization: Julius-Maximilians-Universität Würzburg – sequence: 13 givenname: Holger orcidid: 0000-0001-9264-1726 surname: Braunschweig fullname: Braunschweig, Holger organization: Julius-Maximilians-Universität Würzburg – sequence: 14 givenname: Abdou orcidid: 0000-0002-3714-7191 surname: Boucekkine fullname: Boucekkine, Abdou organization: Univ Rennes, Ecole Nationale Supérieure de Chimie de Rennes, CNRS, Institut des Sciences Chimiques de Rennes UMR 6226 – sequence: 15 givenname: Christoph orcidid: 0000-0002-9652-9165 surname: Lambert fullname: Lambert, Christoph organization: Julius-Maximilians-Universität Würzburg – sequence: 16 givenname: Jean‐François orcidid: 0000-0002-2315-4200 surname: Halet fullname: Halet, Jean‐François email: jean-francois.halet@univ-rennes1.fr organization: National Institute for Materials Science (NIMS) – sequence: 17 givenname: Ivo orcidid: 0000-0002-9933-446X surname: Piantanida fullname: Piantanida, Ivo email: Ivo.Piantanida@irb.hr organization: Ruđer Bošković Institute – sequence: 18 givenname: Klaus orcidid: 0000-0002-2857-8379 surname: Müller‐Buschbaum fullname: Müller‐Buschbaum, Klaus email: Klaus.Mueller-Buschbaum@anorg.chemie.uni-giessen.de organization: Justus-Liebig-Universität Gießen – sequence: 19 givenname: Todd B. orcidid: 0000-0002-9990-0169 surname: Marder fullname: Marder, Todd B. email: todd.marder@uni-wuerzburg.de organization: Julius-Maximilians-Universität Würzburg |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/35502627$$D View this record in MEDLINE/PubMed https://hal.science/hal-03690447$$DView record in HAL |
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| Snippet | A series of bis‐(4’‐pyridylethynyl)arenes (arene=benzene, tetrafluorobenzene, and anthracene) were synthesized and their bis‐N‐methylpyridinium compounds were... A series of bis‐(4’‐pyridylethynyl)arenes (arene=benzene, tetrafluorobenzene, and anthracene) were synthesized and their bis‐ N ‐methylpyridinium compounds... A series of bis-(4'-pyridylethynyl)arenes (arene=benzene, tetrafluorobenzene, and anthracene) were synthesized and their bis-N-methylpyridinium compounds were... A series of bis-(4’-pyridylethynyl)arenes (arene = benzene, tetrafluorobenzene, and anthracene) were synthesized and their bis- N -methylpyridinium compounds... |
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| SubjectTerms | Absorption Anthracene Anthracenes Aromatic compounds Benzene Biology cell imaging Cell lines Chemical Sciences Chemistry Chemistry, Multidisciplinary Crystal structure Cytotoxicity Deoxyribonucleic acid DNA DNA - chemistry DNA/RNA binding Electrochemical analysis Electrochemistry Emission analysis Grooves Humans Hydrocarbons Lead compounds Lysosomes Medicinal Chemistry methyl viologen Molecular Structure or physical chemistry Paraquat Photon absorption Photons Physical Sciences Ribonucleic acid RNA Science & Technology Single crystals Singlet oxygen Theoretical and Toxicity two-photon absorption |
| Title | Methyl Viologens of Bis‐(4’‐Pyridylethynyl)Arenes – Structures, Photophysical and Electrochemical Studies, and their Potential Application in Biology |
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