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Beilstein J. Org. Chem. 2010, 6, 992–1001, doi:10.3762/bjoc.6.112
Graphical Abstract
Scheme 1: Structures of 2-phenylethynyltriphenylene derivatives.
Scheme 2: Synthesis of 2-ethynyltriphenylene (4).
Scheme 3: Synthesis of phenylethynyltriphenylene derivatives 1a–g.
Figure 1: Absorption spectra of 1a–g in cyclohexane and acetonitrile (10−5 M).
Figure 2: Fluorescence emission spectra of 1a–g in cyclohexane and DMSO (10−5 M), λex = 335 nm.
Figure 3: Fluorescence emission spectra of 1e and 1g in various solvents (10−5 M). CH – cyclohexane (λex = 33...
Figure 4: Effect of binary solvent system (cyclohexane-isopropyl alcohol) on the fluorescence emission of 1g ...
Figure 5: Lippert–Mataga plot showing Stokes shift as a function of solvent orientation polarizibility (Δf).
Figure 6: Correlation of Stokes shift with ET(30) scale.
Figure 7: HOMO and LUMO surfaces of 1c and 1g according to DFT calculations.