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Beilstein J. Org. Chem. 2024, 20, 243–253, doi:10.3762/bjoc.20.24
Graphical Abstract
Scheme 1: Comparison of basicity (in water scale) and synthetic availability of quinoline-type azaarenes and ...
Figure 1: Suggested amination products 6 and two resonance forms of dianion 7.
Figure 2: Targeted dipyridoacenaphthylene 8.
Scheme 2: Formation of complex 9 and its slow hydrolytic degradation into protic salt 5·HCl.
Figure 3: Molecular and crystal structure of salt 5·HCl·2H2O is strongly dominated by severe H-bonding (blue ...
Figure 4: Selected images of the supramolecular organization of two molecules of base 5 held by 4,6-dichloror...
Figure 5: Fragment of the crystal packing of neutral dipyridoacenaphthene 5 showing self-association via mult...
Scheme 3: Dinitration of compound 5 and the initially assumed admixture 11.
Scheme 4: Mononitration of compound 5.
Figure 6: Structure of dinitroacenaphthylene 12.
Scheme 5: Dehydrogenation of compounds 10 and 11.
Scheme 6: Nucleophilic methoxylation of compounds 10(12).
Figure 7: Basicity of key compounds in acetonitrile.
Scheme 7: Electrophilic bromination of compound 5.
Scheme 8: tele-Elimination upon interaction of dibromide 15 with pyrrolidine.
Scheme 9: Interaction of dibromide 15 with anionic bases.
Beilstein J. Org. Chem. 2023, 19, 674–686, doi:10.3762/bjoc.19.49
Figure 1: Proton sponge-based 1,4-diaryl-1,3-butadiynes synthesized previously and in this study.
Figure 2: Target oligomers as push–pull and cross-conjugated π-systems.
Scheme 1: Synthetic strategy for target oligomers 5.
Scheme 2: Synthesis of 7-(arylethynyl)-2-ethynyl-DMAN 6.
Scheme 3: Synthesis of 1,4-diaryl-1,3-butadiynes 5 and their salts 11.
Figure 3: Molecular structures of compounds 5b (top), 5d (middle), and 5e (bottom).
Figure 4: Views on the molecular backbone of compounds 5b (top), 5d (middle), and 5e (bottom) along the napht...
Scheme 4: Transformation of butadiyne 5c into benzo[g]indole 12.
Figure 5: Molecular structure of compound 11c: frontal (top; BF4− omitted) and side views (bottom; hydrogen a...
Figure 6: Calculation of the qr parameter.
Figure 7: Two π-conjugation ways in oligomers 5.
Figure 8: UV–vis spectra of oligomers 5 (blue line), monomers 6 (red line), and butadiyne 1 (green line).
Figure 9: UV–vis spectra of salts 11 (left), 1·2HBF4 and 6b·HBF4 (right) in acetonitrile.
Figure 10: π-Conjugation pathway in salts 11b and 6b·HBF4.
Figure 11: Cyclic voltammograms of oligomers 5.
Scheme 5: Possible ways of one- and two-electron oxidation of oligomers 5.