Hydrogen-Bond-Mediated Template Synthesis of Rotaxanes, Catenanes, and Knotanes

Schalley, Christoph A.; Weilandt, Torsten; Brüggemann, Jens; Vögtle, Fritz

doi:10.1007/b99913

Cited by 139 publications

(52 citation statements)

References 231 publications

(276 reference statements)

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“…[4] Basic building blocks in this type of supramolecular chemistry are macrocycles and linear molecules, which, for example, in rotaxanes, act as wheels and axles, respectively. [5][6][7] Several studies have been performed on the adsorption and ordering of rotaxanes, [8,9] catenanes, [10,11] or building blocks of such interlocked molecules [12,13] on surfaces.…”

Section: Introductionmentioning

confidence: 99%

“…For instance, for rotaxanes it may provide a possibility to study in detail the threading process of the axles through the wheels involved in the synthesis [6,7] by using scanning probe microscopy. Furthermore, it constitutes a first step towards the design of 2D functional arrays of these molecules, possibly suited for applications.…”

Section: Introductionmentioning

confidence: 99%

“…The amide groups are involved in particular in the formation of twofold hydrogen bonds during the threading process in the rotaxanes synthesis. [6] In the following, we will name the molecule simply as TLM (tetralactam macrocycle). The macrocycle is nonplanar and despite its rigidifying building blocks rather flexible.…”

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Highly Ordered 2D Hydrogen‐Bonded Structures of a Tetralactam Macrocycle on the Au(111) Surface

Kossev

Reckien

Kirchner

et al. 2007

Adv Funct Materials

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Monolayers of a tetralactam macrocycle, which are commonly used as building blocks in the synthesis of rotaxanes or catenanes, are deposited on a Au(111) surface by using vapor deposition. Due to self‐organization, 2D highly ordered supramolecular networks form. From scanning tunneling microscopy (STM) and concomitant density‐function theory calculations, two structurally different phases are found. In both phases, pairs of hydrogen bonds between the amide groups of next‐neighbor macrocycles are responsible for the structural arrangement of the macrocycles. The structure of both phases differs from that of bulk lattice planes, which reveals that the Au(111) surface acts as a template for the growth of the specific 2D structures. These networks of tetralactam macrocycles possibly open a route to study mechanical interlocking processes or guest/host interactions of the molecules in further detail by using STM.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Highly Ordered 2D Hydrogen‐Bonded Structures of a Tetralactam Macrocycle on the Au(111) Surface

Kossev

Reckien

Kirchner

et al. 2007

Adv Funct Materials

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“…MS spectra were recorded with a JEOL JMS-700 spectrometer. Preparative chemical yield [31][32][33][34][35] than before [36]. Covalent methods [37], which were not thought to be versatile for the synthesis of interlocked molecules, were also well developed [38,39].…”

Section: Methodsmentioning

confidence: 99%

The Asymmetry is Derived from Mechanical Interlocking of Achiral Axle and Achiral Ring Components –Syntheses and Properties of Optically Pure [2]Rotaxanes–

et al. 2018

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Rotaxanes consisting of achiral axle and achiral ring components can possess supramolecular chirality due to their unique geometrical architectures. To synthesize such chiral rotaxanes, we adapted a prerotaxane method based on aminolysis of a metacyclophane type prerotaxane that had planar chirality, which is composed of an achiral stopper unit and a crown ether type ring component. The prerotaxanes were well resolved using chiral HPLC into a pair of enantiomerically pure prerotaxanes, which were transferred into corresponding chiral rotaxanes, respectively. Obtained chiral rotaxanes were revealed to have considerable enantioselectivity.

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“…The so-called amide catenanes whose formation is templated by hydrogenbonding interactions were discovered independently in the early 1990s by Hunter (1992) and Vögtle (Vögtle et al 1992). Their discovery has led to a new generation of neutral MIMs synthesized using the stabilization and directionality provided by hydrogen bonds (Schalley et al 2004).…”

Section: Synthetic Approaches To Mechanically Interlocked Moleculesmentioning

confidence: 99%

Mechanostereochemistry and the mechanical bond

2012

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The chemistry of mechanically interlocked molecules (MIMs), in which two or more covalently linked components are held together by mechanical bonds, has led to the coining of the term mechanostereochemistry to describe a new field of chemistry that embraces many aspects of MIMs, including their syntheses, properties, topologies where relevant and functions where operative. During the rapid development and emergence of the field, the synthesis of MIMs has witnessed the forsaking of the early and grossly inefficient statistical approaches for template-directed protocols, aided and abetted by molecular recognition processes and the tenets of self-assembly. The resounding success of these synthetic protocols, based on templation, has facilitated the design and construction of artificial molecular switches and machines, resulting more and more in the creation of integrated functional systems. This review highlights (i) the range of template-directed synthetic methods being used currently in the preparation of MIMs; (ii) the syntheses of topologically complex knots and links in the form of stable molecular compounds; and (iii) the incorporation of bistable MIMs into many different device settings associated with surfaces, nanoparticles and solid-state materials in response to the needs of particular applications that are perceived to be fair game for mechanostereochemistry.

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Hydrogen-Bond-Mediated Template Synthesis of Rotaxanes, Catenanes, and Knotanes

Cited by 139 publications

References 231 publications

Highly Ordered 2D Hydrogen‐Bonded Structures of a Tetralactam Macrocycle on the Au(111) Surface

Highly Ordered 2D Hydrogen‐Bonded Structures of a Tetralactam Macrocycle on the Au(111) Surface

The Asymmetry is Derived from Mechanical Interlocking of Achiral Axle and Achiral Ring Components –Syntheses and Properties of Optically Pure [2]Rotaxanes–

Mechanostereochemistry and the mechanical bond

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