Complexation of Fullerenes by Subphthalocyanine Dimers

Henrik Gotfredsen; Thomas Holmstrøm; Alberto Viñas Muñoz; Freja Eilsø Storm; Christian G Tortzen; Anders Kadziola; Kurt V Mikkelsen; Ole Hammerich; Mogens Brøndsted Nielsen

doi:10.1021/acs.orglett.8b02518

Complexation of Fullerenes by Subphthalocyanine Dimers

Org Lett. 2018 Sep 21;20(18):5821-5825. doi: 10.1021/acs.orglett.8b02518. Epub 2018 Sep 13.

Authors

Henrik Gotfredsen¹, Thomas Holmstrøm¹, Alberto Viñas Muñoz¹, Freja Eilsø Storm¹, Christian G Tortzen¹, Anders Kadziola¹, Kurt V Mikkelsen¹, Ole Hammerich¹, Mogens Brøndsted Nielsen¹

Affiliation

¹ Department of Chemistry , University of Copenhagen , Universitetsparken 5 , DK-2100 Copenhagen Ø , Denmark.

PMID: 30211563
DOI: 10.1021/acs.orglett.8b02518

Abstract

Tweezer-like molecules comprised of two boron subphthalocyanine (SubPc) units were prepared by Sonogashira couplings and investigated using NMR spectroscopy for their ability to bind fullerenes (C₆₀ and C₇₀). The preorganization of the tweezers provided association constants of ca. 10³ M^-1 in toluene- d₈, while a SubPc monomer did not show any association. Nevertheless, the SubPc monomer crystallized with the fullerenes as 2:1 complexes, supporting the favorable tweezer-like design for complexation, which was further corroborated by computations.

Publication types

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