Refine
Has Fulltext
- yes (8)
Is part of the Bibliography
- yes (8)
Document Type
- Journal article (7)
- Doctoral Thesis (1)
Language
- English (8)
Keywords
- boranes (4)
- singlet oxygen (3)
- DNA/RNA sensors (2)
- chromophore (2)
- fluorescent probes (2)
- synthetic methods (2)
- Biomacromolecular Sensing (1)
- Boron Materials (1)
- Chemical Synthesis (1)
- Chemische Synthese (1)
- DNA-Sensor (1)
- DNA/RNA binding (1)
- Fotophysik (1)
- Lewis acid (1)
- Photophysics (1)
- Raman probes (1)
- Singlett Oxygen (1)
- Singulettsauerstoff (1)
- Triarylborane (1)
- arylmetalate (1)
- bioimaging (1)
- boric acid (1)
- boron (1)
- borylation (1)
- cell imaging (1)
- functionalization (1)
- luminescence (1)
- methyl viologen (1)
- molecular modelling (1)
- nucleic acid (1)
- optical materials (1)
- room-temperature phosphorescence (RTP) (1)
- theranostics (1)
- two-photon absorption (1)
Institute
- Institut für Anorganische Chemie (8) (remove)
We report four new luminescent tetracationic bis-triarylborane DNA and RNA sensors that show high binding affinities, in several cases even in the nanomolar range. Three of the compounds contain substituted, highly emissive and structurally flexible bis(2,6-dimethylphenyl-4-ethynyl)arene linkers (3: arene=5,5′-2,2′-bithiophene; 4: arene=1,4-benzene; 5: arene=9,10-anthracene) between the two boryl moieties and serve as efficient dual Raman and fluorescence chromophores. The shorter analogue 6 employs 9,10-anthracene as the linker and demonstrates the importance of an adequate linker length with a certain level of flexibility by exhibiting generally lower binding affinities than 3–5. Pronounced aggregation–deaggregation processes are observed in fluorimetric titration experiments with DNA for compounds 3 and 5. Molecular modelling of complexes of 5 with AT-DNA, suggest the minor groove as the dominant binding site for monomeric 5, but demonstrate that dimers of 5 can also be accommodated. Strong SERS responses for 3–5 versus a very weak response for 6, particularly the strong signals from anthracene itself observed for 5 but not for 6, demonstrate the importance of triple bonds for strong Raman activity in molecules of this compound class. The energy of the characteristic stretching vibration of the C≡C bonds is significantly dependent on the aromatic moiety between the triple bonds. The insertion of aromatic moieties between two C≡C bonds thus offers an alternative design for dual Raman and fluorescence chromophores, applicable in multiplex biological Raman imaging.