Synthetic Doping of Diamondoids through Skeletal Editing
Andrey A. Fokin, Olga K. Reshetylova, Vladyslav V. Bakhonsky, Alexander Pashenko, Alena Kivernik, Tatyana S. Zhuk, Jonathan Becker, Jeremy Dahl, Robert M. K. Carlson, Peter R. Schreiner
Abstract
We present a strategy for the skeletal editing of diamondoid structures to selectively displace methylene for heteroatom moieties in the carbon framework. This constitutes a synthetic approach to doping diamond-like structures with electron donor dopants (O, N, and S). The key steps involve two subsequent retro-Barbier fragmentations followed by cage reconstruction in the presence of a dopant. Remarkably, the incorporation of n-dopants reduces the strain of the diamondoid cage as shown through homodesmotic equations.
Topics & Concepts
DiamondoidHeteroatomDopantChemistryDopingDiamondStereochemistryMoleculeNanotechnologyCrystallographyComputational chemistryOrganic chemistryMaterials scienceOptoelectronicsRing (chemistry)Diamond and Carbon-based Materials ResearchAdvanced Memory and Neural ComputingSemiconductor materials and devices