Efficient synthesis of fluorinated triphenylenes with enhanced arene–perfluoroarene interactions in columnar mesophases

• Yang Chen,
• Jiao He,
• Hang Lin,
• Hai-Feng Wang,
• Ping Hu,
• Bi-Qin Wang,
• Ke-Qing Zhao and
• Bertrand Donnio

Beilstein J. Org. Chem. 2024, 20, 3263–3273, doi:10.3762/bjoc.20.270

• -tetraalkoxy-3-(perfluorophenyl)triphenylenes (Fn). They were obtained by reacting the above mentioned 2,2’-dilithiobiphenyl derivatives with decafluorobiphenyl, C6F5–C6F5. These compounds differ from the previously reported series, 1,2,4-trifluoro-6,7,10,11-tetraalkoxy-3-aryltriphenylenes (PHn), solely by the

• red-shift of the emission peak. Keywords: arene–perfluoroarene interaction; decafluorobiphenyl; fluorinated triphenylene; fluoroarene nucleophilic substitution; organolithium; Introduction Non-covalent arene–fluoroarene intermolecular interactions [1][2] are drawing increasing attention due to their

• perfluorobenzene, perfluoropyridine, perfluoronaphthalene, decafluorobiphenyl, and many other synthesized perfluoroarenes, and the nucleophiles are also abundant and contain aryllithium, conjugated organic dilithium reagents, phenols and benzenethiols, etc. [35][36][37][38][39][40][41][42][43]. We recently

Star-shaped tetrathiafulvalene oligomers towards the construction of conducting supramolecular assembly

• Masahiko Iyoda and
• Masashi Hasegawa

Beilstein J. Org. Chem. 2015, 11, 1596–1613, doi:10.3762/bjoc.11.175

• of α-protons of pyrroles in the 1H NMR spectra: δ 6.89 (38), 6.41 (40), 5.93 ppm (42). Star-shaped TTF 10-mer 44 was also synthesized by SNAr reaction of the sodium salt of 36 with decafluorobiphenyl (44%) [75] (Figure 13). In the CV measurements (Figure 14), tetrasubstituted 40 shows typical two