C3v-symmetrical tribenzotriquinacenes extended by six C1-functional groups and the first triquinacene-based tris(dithiametacyclophanes).
The first examples of novel bowl-shaped tribenzotriquinacenes (TBTQs) bearing three dithiametacyclophane units within their arene peripheries are reported. The synthesis is based on a C3v-symmetrical hexakis(chloromethyl)tribenzotriquinacene as the key intermediate and yields the inter-ring metacyclophane-type macrocyclization instead of the intra-ring orthocyclophane-type cyclocondensation. Multiple nucleophilic substitution of the same key intermediate leads to a number of other new 6-fold functionalized tribenzotriquinacenes, some of which may be of interest as readily accessible building blocks for the construction of novel bowl-shaped organic networks. The molecular structures of the novel tris(dithiametacyclophanes) and of the hexakis(chloromethyl)- and hexakis(hydroxymethyl)tribenzo-triquinacenes have been determined by X-ray analysis and interesting host/guest aggregation and torsional effects in the solid state are discussed.
State Key Laboratory of Applied Organic Chemistry and College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, People's Republic of China.
Ling
L
Zhou
Tao-Xiang
TX
Zhang
Bing-Rui
BR
Li
Xiao-Ping
XP
Cao
Dietmar
D
Kuck