3,5-Bis(trimethylsilyl)triphenyleno[1,12-bcd]thiophene

Abstract

In the title compound, C24H26SSi2, the fused ring system plus the two Si atoms are coplanar, consistent with planar triphenylene but contrary to bowl‐shaped triphenyleno[1,12‐bcd:4,5‐b′c′d′:8,9‐b′′c′′d′′]trithiophene. The bond alternation pattern of the C—C bonds in the title compound is similar to that found in triphenyleno[1,12‐bcd:4,5‐b′c′d′:8,9‐b′′c′′d′′]trithiophene, although the lengths of the C—C bonds around the central and thiophene rings of the title compound are slightly different from the corresponding bonds of triphenyleno[1,12‐bcd:4,5‐b′c′d′:8,9‐b′′c′′d′′]trithiophene.

Synthesis, structures and optical properties of trisilasumanene and its related compounds

“…13 The C-C bonds in the central six-membered ring slightly alternate from 1.404 A ˚to 1.471 A ˚, and the degree of alternation in 2 is larger than those found in the parent triphenylene (1.411-1.470 A ˚)13 and sumanene (1.38-1.431 A ˚), 2 but is smaller than that of triphenylenothiophene (1.375-1.467 A ˚). 14 The p-framework of 2 is almost planar. In the packing structure of 2, there are no significant intermolecular interactions.…”

Cover Picture: Norrisolide: Total Synthesis and Related Studies (Chem. Eur. J. 24/2005)

“…The C–C bonds in the central six‐membered rings of 9 and 6 alter from 1.382 to 1.475 Å and from 1.381 to 1.445 Å, respectively. The degree of alternation in 6 is comparable to that found in 8 (1.404 to 1.471 Å)25 and heterasumanene 5 (1.367 to 1.450 Å),24 whereas that of 9 is larger than the case of 8 , the parent triphenylene (1.411 to 1.470 Å)30 and sumanene (1.38 to 1.431 Å),31 and it is comparable to the case of triphenylenothiophene (1.375 to 1.467 Å) 32. The large alternation found in 9 is probably caused by the fact that two silole units constrict the triphenylene framework, which lengthens the opposite C(9)–C(10) bond [1.475(3) Å].…”

Arching a bay area of triphenyleno[1,12-bcd]thiophene with group 14 functionalities: Synthesis of the first triphenylene derivatives having thiophene and metallafluorene moieties

“…Protons on the a-carbons of the dibenzothiophene moiety were abstracted more easily than bay protons to afford dilithio derivative 6. Thus, for further fuctionalization of a bay area of 4, the a-carbons of the dibenzothiophene moiety were protected by trimethylsilyl groups to give bis(trimethylsilyl) derivative 7 [10] in 71% yield together with mono-substituted 8 in 8% yield (Scheme 1).…”