Preparation and characterization of metalloporphyrin Tröger's and Spiro-Tröger's base derivatives

0564755 - FZÚ 2023 RIV US eng J - Článek v odborném periodiku
Navrátilová, T. - Tatar, A. - Havlík, M. - Hajduch, J. - Drozdová, M. - Gurung, Kshitij - Palatinus, Lukáš - Čejka, J. - Sedláček, J. - Anzenbacher Jr., P. - Dolenský, B.
Preparation and characterization of metalloporphyrin Tröger's and Spiro-Tröger's base derivatives.
Journal of Organic Chemistry. Roč. 87, č. 22 (2022), s. 15178-15186. ISSN 0022-3263. E-ISSN 1520-6904
Grant CEP: GA MŠMT(CZ) EF16_019/0000760; GA ČR(CZ) GX21-05926X
Grant ostatní: OP VVV - SOLID21(XE) CZ.02.1.01/0.0/0.0/16_019/0000760
Výzkumná infrastruktura: CzechNanoLab - 90110
Institucionální podpora: RVO:68378271
Klíčová slova: metalloporphyrin dimers * Tröger's bases * spiro-Tröger's bases * crystal structure * solvents
Obor OECD: Condensed matter physics (including formerly solid state physics, supercond.)
Impakt faktor: 3.6, rok: 2022
Způsob publikování: Omezený přístup
https://doi.org/10.1021/acs.joc.2c01716

A series of metalloporphyrin dimers as Tröger's bases 1 or spiro-Tröger's bases 2 was prepared starting from five different C4-symmetry porphyrin derivatives substituted in meso-positions by Ph, 3-MeO-Ph, 4-MeO-Ph, 3,4-(MeO)2-Ph, or 3,5-(MeO)2-Ph. Free-base porphyrins were converted to metalloporphyrins, which were subsequently nitrated with nickel(II), copper(II), or zinc(II) nitrate to give β-nitrometalloporphyrins. These were further reduced to β-aminometalloporphyrins and treated with a methanal equivalent under acidic conditions to selectively obtain Tröger's base 1, spiro-Tro ger's base 2, or a mixture of both, in yields up to 41% of 1 and 45% of 2 depending on the reaction conditions used.
Trvalý link: https://hdl.handle.net/11104/0336412