Synthesis and Functionalization of Isomeric Sesquihomodiamantenes

anti- and syn-sesquihomodiamantenes
(SDs) were prepared and structurally characterized. anti-SD and parent sesquihomoadamantene were CH-bond functionalized by
utilizing a phase-transfer protocol. The density functional theory-computed
ionization potentials of unsaturated diamondoid dimers correlate well
with the experimental oxidation potentials obtained from cyclic voltammetry.
Similar geometries ensue for both the reduced and ionized SD states,
whose persistence is supported by the β-hydrogen’s spatial
sheltering. This makes SDs promising building blocks for the construction
of diamond materials with high stability and carrier mobility.