Journal of Organometallic Chemistry, volume 949, pages 121945
First examples of bispidine-ferrocene cyclophanes
Publication type: Journal Article
Publication date: 2021-09-01
Journal:
Journal of Organometallic Chemistry
Quartile SCImago
Q3
Quartile WOS
Q2
Impact factor: 2.3
ISSN: 0022328X
Materials Chemistry
Organic Chemistry
Biochemistry
Inorganic Chemistry
Physical and Theoretical Chemistry
Abstract
Abstract Two approaches for the syntheses of bispidine-ferrocene cyclophanes were reported. Both include the acylation of 1,5-dimethylbispidin-9-one (H2Bp) or its pendant amino-armed derivative by 1,1’-ferrocenoyl (Fc(CO)2) dichloride. The first approach allowed to isolate di-, tri- and pentameric cyclic oligomers of composition (BpFc(CO)2)n. The second one included the preliminary functionalization of H2Bp by N-protected glycine followed by deprotection and cyclization with Fc(COCl)2. The crystal structure of two new bispidine-ferrocene cyclophanes was established by single-crystal X-ray study. This study revealed the anti-conformation of amido-groups attached to the bispidine nitrogen atoms for both molecules. Various NMR techniques were applied to study the solution behavior of the macrocycles; the predominant anti-conformation in solution was also proved. The acyclic model compound Bp(FcCO)2 also showed only anti-conformer as revealed by VT-NMR and X-ray studies. Cyclic voltammetry study showed the difference in oxidation potentials of the Fc moiety within the row Bp(FcCO)2 – (BpFc(CO)2)2 – (BpFc(CO)2)3 with splitting of the oxidation curve in two later cases. The results obtained in this work will find an application in design and study of novel bispidine-ferrocene cyclophanes for the purposes of supramolecular sensing and catalysis.
Citations by journals
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1
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Molecules
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Molecules
1 publication, 25%
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Russian Journal of Organic Chemistry
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Russian Journal of Organic Chemistry
1 publication, 25%
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Russian Journal of General Chemistry
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Russian Journal of General Chemistry
1 publication, 25%
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Organics
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1 publication, 25%
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Citations by publishers
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2
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Multidisciplinary Digital Publishing Institute (MDPI)
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Multidisciplinary Digital Publishing Institute (MDPI)
2 publications, 50%
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Pleiades Publishing
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Pleiades Publishing
2 publications, 50%
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1
2
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Medvedko A. V. et al. First examples of bispidine-ferrocene cyclophanes // Journal of Organometallic Chemistry. 2021. Vol. 949. p. 121945.
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Medvedko A. V., Krutko D. P., Gaisen S. V., Churakov A., Minyaev M. E., Moiseeva A. A., Lemenovsky D. A., Yu H., Wang L., Vatsadze S. Z., Yu H., Wang L. First examples of bispidine-ferrocene cyclophanes // Journal of Organometallic Chemistry. 2021. Vol. 949. p. 121945.
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TY - JOUR
DO - 10.1016/j.jorganchem.2021.121945
UR - https://doi.org/10.1016%2Fj.jorganchem.2021.121945
TI - First examples of bispidine-ferrocene cyclophanes
T2 - Journal of Organometallic Chemistry
AU - Medvedko, Alexey V
AU - Krutko, D P
AU - Gaisen, S V
AU - Churakov, A.V.
AU - Minyaev, Mikhail E.
AU - Moiseeva, A A
AU - Lemenovsky, D A
AU - Yu, Hoi-Fung
AU - Wang, L
AU - Vatsadze, Sergey Z.
AU - Yu, H.
AU - Wang, L.
PY - 2021
DA - 2021/09/01 00:00:00
PB - Elsevier
SP - 121945
VL - 949
SN - 0022-328X
ER -
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@article{2021_Medvedko,
author = {Alexey V Medvedko and D P Krutko and S V Gaisen and A.V. Churakov and Mikhail E. Minyaev and A A Moiseeva and D A Lemenovsky and Hoi-Fung Yu and L Wang and Sergey Z. Vatsadze and H. Yu and L. Wang},
title = {First examples of bispidine-ferrocene cyclophanes},
journal = {Journal of Organometallic Chemistry},
year = {2021},
volume = {949},
publisher = {Elsevier},
month = {sep},
url = {https://doi.org/10.1016%2Fj.jorganchem.2021.121945},
pages = {121945},
doi = {10.1016/j.jorganchem.2021.121945}
}