N-heterocyclic carbenes with three and six fluorous ponytails and their highly fluorophilic Rh and Ir complexes
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F67985858%3A_____%2F23%3A00569339" target="_blank" >RIV/67985858:_____/23:00569339 - isvavai.cz</a>
Alternative codes found
RIV/44555601:13440/23:43897612
Result on the web
<a href="https://hdl.handle.net/11104/0340756" target="_blank" >https://hdl.handle.net/11104/0340756</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1016/j.jorganchem.2022.122605" target="_blank" >10.1016/j.jorganchem.2022.122605</a>
Alternative languages
Result language
angličtina
Original language name
N-heterocyclic carbenes with three and six fluorous ponytails and their highly fluorophilic Rh and Ir complexes
Original language description
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 pre-cursors 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).(c) 2022 Elsevier B.V. All rights reserved.
Czech name
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Czech description
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Classification
Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
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OECD FORD branch
10401 - Organic chemistry
Result continuities
Project
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Continuities
I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace
Others
Publication year
2023
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
Journal of Organometallic Chemistry
ISSN
0022-328X
e-ISSN
1872-8561
Volume of the periodical
986
Issue of the periodical within the volume
FEB 15
Country of publishing house
CH - SWITZERLAND
Number of pages
9
Pages from-to
122605
UT code for WoS article
000915633600001
EID of the result in the Scopus database
2-s2.0-85145830029