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

Paul Kahl; J Philipp Wagner; Ciro Balestrieri; Jonathan Becker; Heike Hausmann; Graham J Bodwell; Peter R Schreiner

doi:10.1002/anie.201602201

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

Angew Chem Int Ed Engl. 2016 Aug 1;55(32):9277-81. doi: 10.1002/anie.201602201. Epub 2016 Jul 1.

Authors

Paul Kahl¹, J Philipp Wagner¹, Ciro Balestrieri², Jonathan Becker³, Heike Hausmann¹, Graham J Bodwell⁴, Peter R Schreiner⁵

Affiliations

¹ Institute of Organic Chemistry, Justus-Liebig-University, Heinrich-Buff-Ring 17, 35392, Giessen, Germany.
² Department of Chemical Sciences, University of Padova, Via Marzolo, 1-35131, Padova, Italy.
³ Institute of Inorganic Chemistry, Justus-Liebig-University, Heinrich-Buff-Ring 17, 35392, Giessen, Germany.
⁴ Department of Chemistry, Memorial University of Newfoundland, St. John's, NL, A1B 3X7, Canada.
⁵ Institute of Organic Chemistry, Justus-Liebig-University, Heinrich-Buff-Ring 17, 35392, Giessen, Germany. prs@uni-giessen.de.

PMID: 27364983
DOI: 10.1002/anie.201602201

Abstract

The fusion of the sp(3) -hybridized parent diamondoid adamantane with the sp(2) -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.

Keywords: allotropy; graphene; materials science; strained molecules; structure elucidation.

Publication types

Research Support, U.S. Gov't, Non-P.H.S.
Research Support, Non-U.S. Gov't