Cyclotriveratrylene-Containing Porphyrins

Jude Deschamps (1) , Adam Langlois (1) , Gaël Martin (2) , Léo Bucher (1, 2) , Nicolas Desbois (2) , Claude P. Gros (2) , Pierre D. Harvey (1)

1 UdeS - Département de chimie [Sherbrooke]
2 ICMUB - Institut de Chimie Moléculaire de l'Université de Bourgogne [Dijon]

The C-3-symmetric cyclotriveratrylene (CTV) was covalently bonded via click chemistry to 1, 2, 3, and 6 zinc(II) porphyrin units to various host for C-60. The binding constants, Ka, were measured from the quenching of the porphyrin fluorescence by C-60. These constants vary between 400 and 4000 M-1 and are considered weak. Computer modeling demonstrated that the zinc(II) porphyrin units, [Zn], exhibit a strong tendency to occupy the CTV cavity, hence blocking the access for C-60 to land on this site. Instead, the pincer of the type [Zn]-[Zn] and in one case [Zn]-CTV, were found to be the most probable geometry to promote host-guest associations in these systems.

Mots clés: supramolecular chemistry; inclusion complexes; fullerene; derivatives; hosts; cages; c-60; dendrimers; molecules; ctv

Domaines: Chimie

Jude Deschamps, Adam Langlois, Gaël Martin, Léo Bucher, Nicolas Desbois, et al.. Cyclotriveratrylene-Containing Porphyrins. Inorganic Chemistry, 2016, 55 (18), pp.9230 - 9239. ⟨10.1021/acs.inorgchem.6b01261⟩. ⟨hal-01399406⟩