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Beilstein J. Org. Chem. 2016, 12, 854–862, doi:10.3762/bjoc.12.84
Graphical Abstract
Figure 1: Structures of biaryl-type benzo[b]quinolizinium derivatives 1a–f.
Scheme 1: Synthesis of 3-bromonaphtho[1,2-b]quinolizinium bromide (4).
Scheme 2: Synthesis of the 3-aryl-substituted naphtho[1,2-b]quinolizinium derivatives 6a–e.
Figure 2: Absorption spectra of derivatives 6a (A), 6c (B), 6d (C), and 6e (D); c = 20 µM; solvents: H2O (red...
Figure 3: Normalized emission spectra of derivatives 6a (A), 6c (B), 6d (C) and 6e (D) (Abs. = 0.10 at excita...
Figure 4: Fluorescence colors of derivative 6e in various solvents; λex = 366 nm. 1: CHCl3, 2: H2O, 3: CH2Cl2...
Scheme 3: Intramolecular charge shift upon excitation in derivatives 6b–e (see Scheme 2 for assignment of substituent...
Figure 5: Plot of the emission energy of 6e versus the solvent polarity parameter ET(30).
Scheme 4: State diagram of the photoexcitation and deactivation pathways of 3-aryl-naphthoquinolizinium deriv...
Figure 6: Structures of biaryl derivatives 7a–c.