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.