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Beilstein J. Org. Chem. 2019, 15, 2678–2683, doi:10.3762/bjoc.15.261
Graphical Abstract
Figure 1: An example of an earlier developed S,N-heterohexacene [13] and general structure of compounds synthesiz...
Scheme 1: Synthesis of aryl-substituted TT derivatives 3a–k, product scope, and yields.
Scheme 2: Synthesis of thieno[3,2-b]thiophen-3(2H)-one 4a–k, product scope, and yields.
Scheme 3: Synthesis of TTI derivatives 6a–o, substrate and product scopes, and yields.
Scheme 4: Alkylation of TTI 6d.
Figure 2: ORTEP diagram for the X-ray structure of compound 7d. Thermal ellipsoids of 50% probability are sho...
Beilstein J. Org. Chem. 2017, 13, 1396–1406, doi:10.3762/bjoc.13.136
Figure 1: ICZ-cored materials for organic electronic devices.
Figure 2: General positions for SEAr in ICZs 1.
Scheme 1: Double nitration of indolo[3,2-b]carbazole 1a.
Figure 3: X-ray single crystal structure of compound 2a. Thermal ellipsoids of 50% probability are presented.
Scheme 2: C2- and C2,8-nitration of indolo[3,2-b]carbazoles 1.
Scheme 3: Reduction of nitro-substituted ICZs 2 and 3.
Scheme 4: Nitration of 6,12-unsubstituted indolo[3,2-b]carbazoles 8.
Figure 4: X-ray single crystal structure of compounds 9b and 10b. Thermal ellipsoids of 50% probability are p...
Scheme 5: Modification of 6,12-dinitro-ICZs 9a,b by electrophilic substitution.
Figure 5: X-ray single crystal structure of compounds 12b and 13b. Thermal ellipsoids of 50% probability are ...
Scheme 6: A possible mechanism for the reduction of 6,12-dinitro-ICZs 9a and 13a.
Scheme 7: Reactions of 6-nitro- and 6,12-dinitro-ICZs with S-nucleophiles.
Scheme 8: Successive substitution of nitro groups in 6,12-dinitro-ICZ 9a with N- and S-nucleophiles.
Beilstein J. Org. Chem. 2015, 11, 1000–1007, doi:10.3762/bjoc.11.112
Figure 1: Natural and synthetic derivatives of thieno[2,3-b]indole.
Scheme 1: Synthetic routes to thieno[2,3-b]indoles.
Scheme 2: Synthesis and thionation of indodin-2-ones 11.
Scheme 3: Synthetic paths to thieno[2,3-b]indole 12a. LR = Lawesson's reagent
Figure 2: Mercury [34] representation of the X-ray crystal structure of 12a. Thermal ellipsoids of 50% probabilit...
Scheme 4: Two-step synthesis of 2-(hetero)aryl substituted thieno[2,3-b]indoles 12.
Scheme 5: Synthesis of mono- and dibromo-substituted thieno[2,3-b]indoles 12n,o.