Ruthenium(iv) N-confused Porphyrin μ-oxo-bridged Dimers: Acid-responsive Molecular Rotors

Overview

Journal RSC Adv

Publisher Royal Society of Chemistry

Specialty Chemistry

Date 2022 Apr 28

PMID 35481054

Authors

Osamu Iwanaga

Kazuki Fukuyama

Shigeki Mori

Jun Tae Song

Tatsumi Ishihara

Takaaki Miyazaki

Masatoshi Ishida

Hiroyuki Furuta

Affiliations

Soon will be listed here.

Abstract

Ruthenium(iv) N-confused porphyrin μ-oxo-bridged complexes were synthesized oxidative dimerization of a ruthenium(ii) N-confused porphyrin complex using 2,2,6,6-tetramethylpiperidine 1-oxyl. The deformed core planes in the dimers conferred a relatively high ring rotational barrier of 16 kcal mol. Rotation of the complexes was controlled by protonating the peripheral nitrogen.

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References

Wang J, Feringa B . Dynamic control of chiral space in a catalytic asymmetric reaction using a molecular motor. Science. 2011; 331(6023):1429-32. DOI: 10.1126/science.1199844. View

Komeda T, Isshiki H, Liu J, Zhang Y, Lorente N, Katoh K . Observation and electric current control of a local spin in a single-molecule magnet. Nat Commun. 2011; 2:217. PMC: 3072104. DOI: 10.1038/ncomms1210. View

Zhao D, Neubauer T, Feringa B . Dynamic control of chirality in phosphine ligands for enantioselective catalysis. Nat Commun. 2015; 6:6652. PMC: 4389239. DOI: 10.1038/ncomms7652. View

Hung C, Chen W, Lee G, Peng S . Dimeric iron n-confused porphyrin complexes. Chem Commun (Camb). 2002; (14):1516-7. DOI: 10.1039/b202679a. View

Goswami A, Saha S, Kumar Biswas P, Schmittel M . (Nano)mechanical Motion Triggered by Metal Coordination: from Functional Devices to Networked Multicomponent Catalytic Machinery. Chem Rev. 2019; 120(1):125-199. DOI: 10.1021/acs.chemrev.9b00159. View

Corra S, Curcio M, Baroncini M, Silvi S, Credi A . Photoactivated Artificial Molecular Machines that Can Perform Tasks. Adv Mater. 2020; 32(20):e1906064. DOI: 10.1002/adma.201906064. View

Yamamoto T, Toganoh M, Furuta H . Cooperation between metal and ligand in oxygen atom transport by N-confused porphyrin oxorhenium(V) complexes. Dalton Trans. 2012; 41(30):9154-7. DOI: 10.1039/c2dt30885a. View

Dial B, Pellechia P, Smith M, Shimizu K . Proton grease: an acid accelerated molecular rotor. J Am Chem Soc. 2012; 134(8):3675-8. DOI: 10.1021/ja2120184. View

Kudernac T, Ruangsupapichat N, Parschau M, Macia B, Katsonis N, Harutyunyan S . Electrically driven directional motion of a four-wheeled molecule on a metal surface. Nature. 2011; 479(7372):208-11. DOI: 10.1038/nature10587. View

10.

Zhang J, Che C . Dichlororuthenium(IV) complex of meso-tetrakis(2,6-dichlorophenyl)porphyrin: active and robust catalyst for highly selective oxidation of arenes, unsaturated steroids, and electron-deficient alkenes by using 2,6-dichloropyridine N-oxide. Chemistry. 2005; 11(13):3899-914. DOI: 10.1002/chem.200401008. View

11.

Abdullin D, Fleck N, Klein C, Brehm P, Spicher S, Lutzen A . Synthesis of μ -Oxo-Bridged Iron(III) Tetraphenylporphyrin-Spacer-Nitroxide Dimers and their Structural and Dynamics Characterization by using EPR and MD Simulations. Chemistry. 2018; 25(10):2586-2596. DOI: 10.1002/chem.201805016. View

12.

Otsuki J, Komatsu Y, Kobayashi D, Asakawa M, Miyake K . Rotational libration of a double-decker porphyrin visualized. J Am Chem Soc. 2010; 132(20):6870-1. DOI: 10.1021/ja907077e. View

13.

Erbas-Cakmak S, Leigh D, McTernan C, Nussbaumer A . Artificial Molecular Machines. Chem Rev. 2015; 115(18):10081-206. PMC: 4585175. DOI: 10.1021/acs.chemrev.5b00146. View

14.

Bialek M, Bialonska A, Latos-Grazynski L . Oxidation and Oxygenation of Carbonyl Ruthenium(II) Azuliporphyrin. Inorg Chem. 2015; 54(13):6184-94. DOI: 10.1021/acs.inorgchem.5b00324. View

15.

van Delden R, Ter Wiel M, Pollard M, Vicario J, Koumura N, Feringa B . Unidirectional molecular motor on a gold surface. Nature. 2005; 437(7063):1337-40. DOI: 10.1038/nature04127. View

16.

Zhang Y, Kersell H, Stefak R, Echeverria J, Iancu V, Perera U . Simultaneous and coordinated rotational switching of all molecular rotors in a network. Nat Nanotechnol. 2016; 11(8):706-12. DOI: 10.1038/nnano.2016.69. View

17.

Fu Y, Schwobel J, Hla S, DiLullo A, Hoffmann G, Klyatskaya S . Reversible chiral switching of bis(phthalocyaninato) terbium(III) on a metal surface. Nano Lett. 2012; 12(8):3931-5. DOI: 10.1021/nl302166z. View

18.

Miyazaki T, Fukuyama K, Mashita S, Deguchi Y, Yamamoto T, Ishida M . Ruthenium N-Confused Porphyrins: Selective Reactivity for Ambident 2-Heteroatom-Substituted Pyridines Serving as Axial Ligands. Chempluschem. 2020; 84(6):603-607. DOI: 10.1002/cplu.201800630. View

19.

Miyake K, Fukuta M, Asakawa M, Hori Y, Ikeda T, Shimizu T . Molecular motion of surface-immobilized double-decker phthalocyanine complexes. J Am Chem Soc. 2009; 131(49):17808-13. DOI: 10.1021/ja904629d. View

20.

Gallo E, Caselli A, Ragaini F, Fantauzzi S, Masciocchi N, Sironi A . Structural determination of ruthenium-porphyrin complexes relevant to catalytic epoxidation of olefins. Inorg Chem. 2005; 44(6):2039-49. DOI: 10.1021/ic048587w. View