A Short Covalent Synthesis of an All-Carbon-Ring [2]Rotaxane

Steemers, Luuk; Wanner, Martin J.; Ehlers, Andreas W.; Hiemstra, Henk; Maarseveen, Jan H. van

doi:10.1021/acs.orglett.7b00877

Cited by 18 publications

(29 citation statements)

References 29 publications

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“…Drawing inspiration from passive metal templating, Godt et al developed a carbonate template for the synthesis of [2]catenanes and polymeric catenanes [12–14] . Höger et al successfully modified its terephthalic ester macrocyclization template to obtain MiMs, and our group later investigated this method as well [15–18] . Other functional groups used for templating include esters [19–22] and imines [23, 24] …”

Section: Methodsmentioning

confidence: 99%

“…[12][13][14] Hçger et al successfully modified its terephthalic ester macrocyclization template to obtain MiMs, and our group later investigated this method as well. [15][16][17][18] Other functional groups used for templating include esters [19][20][21][22] and imines. [23,24] For this work however,w ew eres pecially inspiredb yS chill and colleagues, who,b yt he synthesis of ac atenane,p repared aM iM for the first time and pioneered the field of covalently templated MiM synthesis.…”

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confidence: 99%

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[2]Catenane Synthesis via Covalent Templating

Pilon

Jørgensen

Maarseveen

2021

Chemistry A European J

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After earlier unsuccessful attempts, this work reports the application of covalent templating for the synthesis of mechanically interlocked molecules (MiMs) bearing no supramolecular recognition sites. Two linear strands were covalently connected in a perpendicular fashion by a central ketal linkage. After subsequent attachment of the first strand to a template via temporary benzylic linkages, the second was linked to the template in a backfolding macrocyclization. The resulting pseudo[1]rotaxane structure was successfully converted to a [2]catenane via a second macrocyclization and cleavage of the ketal and temporary linkages.

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Section: Methodsmentioning

confidence: 99%

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confidence: 99%

[2]Catenane Synthesis via Covalent Templating

Pilon

Jørgensen

Maarseveen

2021

Chemistry A European J

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“…Our group has also employed a terephthalic acid template in the synthesis of rotaxanes, as shown in Scheme 20. 53 Compound 77 was decorated with acetylene and olefin groups to allow for Scheme 17 Morin's attempted rotaxane synthesis using cleavable ester linkages between axle and thread. 49 around the axle, after which catalytic hydrogenation yielded prerotaxane 80.…”

Section: Accepted Manuscriptmentioning

confidence: 99%

“…51 Template Scheme 20 Synthesis of [2]rotaxane 81 through hydrolysis of the terephthalic acid template as reported by our group. 53 interlocked rings. Both axle and macrocycle could be functionalized at a late stage in the synthesis, demonstrating the suitability of this method for the preparation of functional hetero[n]rotaxanes.…”

Section: Accepted Manuscriptmentioning

confidence: 99%

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Covalently Templated Syntheses of Mechanically Interlocked Molecules

Maarseveen¹,

Cornelissen²,

Pilon³

2021

Synthesis

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Mechanically interlocked molecules (MiMs) such as catenanes and rotaxanes exhibit unique properties due to the mechanical bond which unites their components. The translational and rotational freedom present in these compounds may be harnessed to create stimuli-responsive MiMs, which find potential application as artificial molecular machines. Mechanically interlocked structures such as lasso peptides have also been found in nature, making MiMs promising albeit elusive targets for drug discovery. Although the first syntheses of MiMs were based on covalent strategies, approaches based on non-covalent interactions rose to prominence thereafter and have remained dominant. Non-covalent strategies are generally short and efficient, but do require particular structural motifs which are difficult to alter. In a covalent approach, MiMs can be more easily modified while the components may have increased rotational and translational freedom. Both approaches have complementary merits and combining the unmatched efficiency of non-covalent approaches with the scope of covalent syntheses may open up vast opportunities. In this review, recent covalently templated syntheses of MiMs are discussed to show their complementarity and anticipate future developments in this field.

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Multifunctional π‐Conjugated Additives for Halide Perovskite

et al. 2022

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Additive is a conventional way to enhance halide perovskite active layer performance in multiaspects. Among them, π‐conjugated molecules have significantly special influence on halide perovskite due to the superior electrical conductivity, rigidity property, and good planarity of π‐electrons. In particular, π‐conjugated additives usually have stronger interaction with halide perovskites. Therefore, they help with higher charge mobility and longer device lifetime compared with alkyl‐based molecules. In this review, the detailed effect of conjugated molecules is discussed in the following parts: defect passivation, lattice orientation guidance, crystallization assistance, energy level rearrangement, and stability improvement. Meanwhile, the roles of conjugated ligands played in low‐dimensional perovskite devices are summarized. This review gives an in‐depth discussion about how conjugated molecules interact with halide perovskites, which may help understand the improved performance mechanism of perovskite device with π‐conjugated additives. It is expected that π‐conjugated organic additives for halide perovskites can provide unprecedented opportunities for the future improvement of perovskite devices.

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A Short Covalent Synthesis of an All-Carbon-Ring [2]Rotaxane

Cited by 18 publications

References 29 publications

[2]Catenane Synthesis via Covalent Templating

[2]Catenane Synthesis via Covalent Templating

Covalently Templated Syntheses of Mechanically Interlocked Molecules

Multifunctional π‐Conjugated Additives for Halide Perovskite

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