Complexation of Fullerenes by Subphthalocyanine Dimers

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

doi:10.1021/acs.orglett.8b02518.s001

ol8b02518_si_001.pdf (10.6 MB)

Complexation of Fullerenes by Subphthalocyanine Dimers

journal contribution

posted on 2018-09-13, 14:48 authored by Henrik Gotfredsen, Thomas Holmstrøm, Alberto Viñas Muñoz, Freja Eilsø Storm, Christian G. Tortzen, Anders Kadziola, Kurt V. Mikkelsen, Ole Hammerich, Mogens Brøndsted Nielsen

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.