PUB - Publikationen an der Universität Bielefeld

Centrohexaindane (C41H24), a structurally unique polyaromatic hydrocarbon bearing six mutually fused indane wings stretched out along the Cartesian axes of space, may be viewed as a seed for the construction of covalent and supramolecular three-dimensional frameworks. A kaleidoscope of established and yet-to-be-explored aspects of centrohexaindane chemistry is presented in this article. After addressing some ideas about the naked centrohexacyclic (and topologically nonplanar) C17-core, which can be considered a "centrohexaquinacyne", the diversity of known but mostly unknown functionalization patterns at the framework of centrohexaindane is addressed in increasing order of substitution at the twelve equivalent peripheral positions. The variety of centrohexaindanes bearing three identical groups is displayed including a very first access to a centrohexaindane that bears a C3-symmetrically functionalized tribenzotriquinacene (TBTQ) unit and, thus, a potential for 3D oligocondensation. The diversity of known tetra- and hexasubstituted centrohexaindane derivatives is presented and conceivable synthesis strategies are discussed for even more highly functionalized derivatives. Finally, the successful access to centrohexaindanes with exhaustive functionalization and hydrocarbon extension at the twelve peripheral positions completes this overview on what may be a vastly open field, still. Multiple functionalization of the unique three-dimensional framework of centrohexaindane is discussed in terms of known and yet unknown substitution patterns at the molecular periphery. The potential to employ centrohexaindane derivatives for various molecular extensions in the 3-space, including the generation of three-dimensional organic networks based on the C17-centrohexaquinacene motif, is addressed as a perspective. image