[2](1,3)Adamantano[2](2,7)pyrenophane: A Hydrocarbon with a Large Dipole Moment

• Published in: Angewandte Chemie (International ed.) Vol. 55; no. 32; pp. 9277 - 9281
• Main Authors: Kahl, Paul, Wagner, J. Philipp, Balestrieri, Ciro, Becker, Jonathan, Hausmann, Heike, Bodwell, Graham J., Schreiner, Peter R.
• Format: Journal Article
• Language: English
• Published: WEINHEIM Blackwell Publishing Ltd 01.08.2016; Wiley; Wiley Subscription Services, Inc; Wiley Blackwell (John Wiley & Sons)
• Edition: International ed. in English
• Subjects: allotropy; Chemistry; Chemistry, Multidisciplinary; Diamonds; Dipole moments; graphene; Hybridization; Hydrocarbons; materials science; Optical properties; Physical Sciences; Pyrene; Science & Technology; strained molecules; structure elucidation; Synthesis; strained molecules; CONFORMATIONAL ISOMORPHISM; PYRENE MOIETY; materials science; DIAMOND; COMPLEXES; CRYSTAL; POLYMORPHISM; graphene; STRAINED ADAMANTANOPHANES; NONPLANAR AROMATIC-COMPOUNDS; structure elucidation; allotropy; PROSPECTS; SURFACES
• ISSN: 1433-7851; 1521-3773
• DOI: 10.1002/anie.201602201

The fusion of the sp3‐hybridized parent diamondoid adamantane with the sp2‐hybridized pyrene results in a hybrid structure with a very large dipole moment which arises from bending the pyrene moiety. Presented herein is the synthesis, study of the electronic and optical properties, as well as the dynamic behavior of this new hydrocarbon. Diamond in the rough: Molecular electronics with single hydrocarbons may be possible by combining the sp3‐hybridized diamond with sp2‐hybridized graphene carbon allotropes. This combination is mimicked through the combination of a diamondoid with pyrene as a graphene model. The nonpolar components lead to a new, highly strained hydrocarbon with a very large and optimally positioned dipole moment needed for molecular rectification.