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Beilstein J. Org. Chem. 2019, 15, 1257–1261, doi:10.3762/bjoc.15.122
Graphical Abstract
Figure 1: BN-phenanthrene 1a and synthesis of substituted derivatives proposed in this work.
Scheme 1: Synthesis of Cl-substituted BN-phenanthrene 1b.
Scheme 2: Palladium-catalyzed cross-couplings of Cl-substituted BN-phenanthrene 1b.
Scheme 3: Pd-catalyzed Sonogashira reactions of Cl-substituted BN-phenanthrene 1b.
Figure 2: UV–vis absorption (top) and emission (bottom) spectra for BN-phenanthrenes 1 and 5 in cyclohexane (...
Figure 3: Solutions of 1a–f and 5 (from left to right) under UV irradiation.
Beilstein J. Org. Chem. 2017, 13, 2902–2914, doi:10.3762/bjoc.13.283
Scheme 1: Chemical structures of TO and SYBR Green I – commercial monomethine fluorescent dsDNA binders.
Scheme 2: Synthesis of the monofluoro-substituted dye TO-1F. Reagents, conditions and yields: (i) sodium meth...
Scheme 3: Synthesis of new halogen-containing analogues of TO. Reagents, conditions and yields: (i) DMS, 100 ...
Figure 1: Absorption spectra of the studied compounds in MeOH (c = 1 × 10−5 M).
Figure 2: Absorption spectra of dye 5b (c = 5 × 10−7 M) in TE buffer, in the absence and presence of dsDNA (c...
Figure 3: Fluorescence spectra of dye 5a (c = 5 × 10–7 M) in TE buffer and in the presence of increasing conc...
Figure 4: Photostability of dyes TO-7Cl and 5a–d in acetonitrile in the concentration range of 1 × 10−5 M.
Figure 5: B3LYP optimized structures.
Figure 6: Graphical representation of the frontier orbitals (isodensity plot, isovalue = 0.02 a.u.).
Figure 7: Simulated TDPBE0 spectra in methanol.
Figure 8: Electron density (isovalue = 0.002) mapped with electrostatic potential (color scheme: green for ne...