Preparation of and dynamic gearing in cis-1,2-bis(9-triptycyl)ethylene

Kawada, Yuzo; Sakai, Hiromi; Oguri, Makoto; Koga, G.

doi:10.1016/0040-4039(94)88184-7

Cited by 34 publications

(36 citation statements)

References 11 publications

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“…b) Molecular gear train 2 60. c) Vinyl molecular gear 3 (shown as the racemic residual diastereomer);61 a molecular gear 4 with a 2:3 gearing ratio;62j and a molecular gear 5 based on revolution around a metallocene and with a 3:4 gearing ratio 63. The arrows show correlated motions but are not meant to imply intrinsic directionality.…”

Section: Controlling Motion In Covalently Bonded Molecular Systemsmentioning

confidence: 99%

“…Dynamic gearing has also been realized in vicinally linked triptycyl rotors, such as 3 (Scheme 1 c),61 and in systems with gearing ratios other than 3:3, for example, 2:3 ( 4 ),62 and 3:4 ( 5 ) 63. Although the low‐energy dynamic processes observed in 5 could not be unequivocally shown to be correlated, this system is one of the first molecular structures in which the facile rotation of π fragments in metallocenes was utilized, thus prompting analogy with a ball bearing 64…”

Section: Controlling Motion In Covalently Bonded Molecular Systemsmentioning

confidence: 99%

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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: 99%

Section: Controlling Motion In Covalently Bonded Molecular Systemsmentioning

confidence: 99%

Synthetic Molecular Motors and Mechanical Machines

2006

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“…Following this, the use of three consecutive bonds was investigated to see if the angle and/or distance between the two 9‐triptycenyl groups would vary significantly, effecting the tightness of gearing in these systems. A cis ‐vinylene group was employed as the connecting group to synthesize cis ‐1,2‐bis(9‐triptycenyl)ethylene 239 through the hydrogenation of a ethynyl linker 238 (Figure ) …”

Section: Applications Of Rigid‐linear Linkers In Molecular Rods and Rmentioning

confidence: 99%

“…A cis-vinylene group was employed as the connecting group to synthesize cis-1,2bis(9-triptycenyl)ethylene 239 throught he hydrogenation of a ethynyll inker 238 (Figure 38). [293] Work with molecular machines was first pioneered and developedb yJ ean-PierreS auvage, Sir J. Fraser Stoddart, and Bernard L. Feringa, who were awarded the 2016 Nobel prize "for the design and synthesiso fm olecularm achines". [294] The interest in functional molecular machines first began in the nineties when the real time rotationo fa nA TP synthase macromolecular motor was observed.…”

Section: Molecular Rotorsmentioning

confidence: 99%

Nonconjugated Hydrocarbons as Rigid‐Linear Motifs: Isosteres for Material Sciences and Bioorganic and Medicinal Chemistry

Locke

Bernhard

Senge

2019

Chemistry A European J

197

143

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Nonconjugated hydrocarbons, like bicyclo[1.1.1]pentane, bicyclo[2.2.2]octane, triptycene, and cubane are a unique class of rigid linkers. Due to their similarity in size and shape they are useful mimics of classic benzene moieties in drugs, so‐called bioisosteres. Moreover, they also fulfill an important role in material sciences as linear linkers, in order to arrange various functionalities in a defined spatial manner. In this Review article, recent developments and usages of these special, rectilinear systems are discussed. Furthermore, we focus on covalently linked, nonconjugated linear arrangements and discuss the physical and chemical properties and differences of individual linkers, as well as their application in material and medicinal sciences.

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“…b) Das mehrstufige molekulare Getriebe 2 60. c) Das molekulare Getriebe 3 mit Vinylgruppe (als racemisches Torsionsdiastereomer);61 das molekulare Getriebe 4 mit einem Zahnkranzverhältnis von 2:3;62j das molekulare Getriebe 5 mit drehbarer Metallocengruppe und einem Zahnkranzverhältnis von 3:4 63. Die Pfeile weisen auf die korrelierten Bewegungen hin, sollen aber keine Vorzugsrichtung andeuten.…”

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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Preparation of and dynamic gearing in cis-1,2-bis(9-triptycyl)ethylene

Cited by 34 publications

References 11 publications

Synthetic Molecular Motors and Mechanical Machines

Synthetic Molecular Motors and Mechanical Machines

Nonconjugated Hydrocarbons as Rigid‐Linear Motifs: Isosteres for Material Sciences and Bioorganic and Medicinal Chemistry

Synthetische molekulare Motoren und mechanische Maschinen

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