A Redox-Mediated Molecular Brake:  Dynamic NMR Study of 2-[2-(Methylthio)phenyl]isoindolin-1-one and <i>S</i>-Oxidized Counterparts

Jog, Parag V.; Brown, R. W.; Bates, Dallas K.

doi:10.1021/jo034613g

Cited by 39 publications

(16 citation statements)

References 42 publications

(23 reference statements)

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“…In the resulting “molecular brake” 8 (Scheme 2 a),68 free rotation of a triptycyl group is halted by the conformational change brought about by complexation of the appended bipyridyl unit with Hg 2+ ions, thus effectively putting a “stick” in the “spokes” 69. A similar “braking effect” has been demonstrated by using redox chemistry and N ‐arylindolinone 9 (Scheme 2 b); both oxidized forms of the sulfur side chain exhibit markedly increased barriers to rotation around the Naryl bond (see also 45 , Scheme 21) 70. 71…”

Section: Controlling Motion In Covalently Bonded Molecular Systemsmentioning

confidence: 87%

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Synthetic Molecular Motors and Mechanical Machines

2006

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The widespread use of controlled molecular-level motion in key natural processes suggests that great rewards could come from bridging the gap between the present generation of synthetic molecular systems, which by and large rely upon electronic and chemical effects to carry out their functions, and the machines of the macroscopic world, which utilize the synchronized movements of smaller parts to perform specific tasks. This is a scientific area of great contemporary interest and extraordinary recent growth, yet the notion of molecular-level machines dates back to a time when the ideas surrounding the statistical nature of matter and the laws of thermodynamics were first being formulated. Here we outline the exciting successes in taming molecular-level movement thus far, the underlying principles that all experimental designs must follow, and the early progress made towards utilizing synthetic molecular structures to perform tasks using mechanical motion. We also highlight some of the issues and challenges that still need to be overcome.

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Section: Controlling Motion In Covalently Bonded Molecular Systemsmentioning

confidence: 87%

“… “Molecular brakes” induced by a) metal‐ion binding68 and b) redox chemistry 70. EDTA=ethylenediaminetetraacetate, m CPBA= meta ‐chloroperbenzoic acid.…”

Section: Controlling Motion In Covalently Bonded Molecular Systemsmentioning

confidence: 99%

Synthetic Molecular Motors and Mechanical Machines

2006

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“…Bildlich gesprochen wird hier ein Stab zwischen die Speichen geschoben 69. Ein ähnlicher Bremseffekt wurde bei Redoxreaktionen mit dem N ‐Arylindolinon 9 nachgewiesen (Schema 2 b); bei oxidierter Schwefelseitenkette (in 9 b und 9 c ) ist die Barriere der Rotation um die N ‐Arylbindung deutlich erhöht (siehe auch 45 in Schema 21) 70. 71…”

Section: Gesteuerte Bewegungen In Kovalent Verknüpften Molekülenunclassified

Synthetische molekulare Motoren und mechanische Maschinen

2006

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In der Natur spielen gesteuerte Bewegungen auf molekularer Ebene bei vielen Prozessen eine Schlüsselrolle. Das Schließen der Lücke zwischen der aktuellen Generation synthetischer Verbindungen, bei denen hauptsächlich elektronische und chemische Effekte genutzt werden, und makroskopischen Maschinen, deren Funktionsfähigkeit auf der synchronisierten Bewegung von Maschinenteilen beruht, wäre ein großer Erfolg. Dieses Forschungsgebiet wird derzeit intensiv bearbeitet und wächst außerordentlich schnell. Die ersten Überlegungen zu molekularen Maschinen reichen allerdings weiter zurück in die Vergangenheit, in eine Zeit, in der die Konzepte vom statistischen Verhalten der Materie und die Gesetze der Thermodynamik formuliert wurden. Wir umreißen hier die Erfolgsgeschichte der Bändigung molekularer Bewegungen, der Beherrschung der grundlegenden Prinzipien, an denen sich das Design zu orientieren hat, und der Fortschritte bei der Anwendung synthetischer Systeme, die durch mechanische Bewegung Aufgaben verrichten können. Ferner werden wir auf einige ungelöste Probleme eingehen.

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“…The modulation of the rotation rate around an N-Ar bond was achieved through a redox-mediated molecular brake by Jog, Brown, and Bates [39]. This consists of the oxidation of sulfide group close to the rotational axis (compound 29) into a sulfoxide 30 and further into a sulfone 31 ( Fig.…”

Section: Controlling the Rate Of Rotationmentioning

confidence: 99%

Synthetic Molecular Machines and Polymer/Monomer Size Switches that Operate Through Dynamic and Non-Dynamic Covalent Changes

Stadler

Ramírez

2011

Constitutional Dynamic Chemistry

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The present chapter is focused on how synthetic molecular machines (e.g. shuttles, switches and molecular motors) and size switches (conversions between polymers and their units, i.e., conversions between relatively large and small molecules) can function through covalent changes. Amongst the interesting examples of devices herein presented are molecular motors and size switches based on dynamic covalent chemistry which is an area of constitutional dynamic chemistry.

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A Redox-Mediated Molecular Brake: Dynamic NMR Study of 2-[2-(Methylthio)phenyl]isoindolin-1-one and S-Oxidized Counterparts

Cited by 39 publications

References 42 publications

Synthetic Molecular Motors and Mechanical Machines

Synthetic Molecular Motors and Mechanical Machines

Synthetische molekulare Motoren und mechanische Maschinen

Synthetic Molecular Machines and Polymer/Monomer Size Switches that Operate Through Dynamic and Non-Dynamic Covalent Changes

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