Reactions of 1-methylimidazole and 1-(1-methylethyl)imidazole with (3-iodopropyl)tris(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)silane gave the corresponding 1-alkyl-3-(3-(tris(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl) silyl) propyl) imidazolium iodides 1 and 2. Reaction of imidazole in excess with (3-iodopropyl)tris(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)silane afforded 1-(3-(tris(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl) silyl) propyl) imidazole 3 which was further reacted with (3-iodopropyl)tris(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)silane to produce the doubly tagged 1,3-bis[3-(tris(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl) silyl) propyl] imidazolium iodide 4 and by anion exchange a tetrafluoroborate salt 5. The prepared imidazolium iodides 1,2, and 4 were then used as precursors in synthesis of chlorido(cycloocta-1,5-diene)rhodium or -iridium complexes bearing Nheterocyclic carbenes with one 3-[tris(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)silyl]propyl-substituent and methyl-, 1-methylethyl-and another 3-[tris(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)silyl]propyl-substituent on nitrogens, 6 – 11. The metal complexes were equimolar mixtures of conformational enantiomers as was best documented by the 1H NMR signals of diastereotopic CH2 protons next to nitrogen. Fluorophilicity fi as the natural logarithm of partition coefficient Pi between fluorous and organic phase of the complexes was determined in the standard solvent system (perfluoro)methylcyclohexane/toluene. All the complexes are fluorophilic with variation of fi between 0.96 and 4.06, the complexes with high values may be classified as highly fluorophilic (heavy fluorous).