Lithium‐Templated Synthesis of a Donor–Acceptor Pseudorotaxane and Catenane

Kaiser, Guido; Jarrosson, Thibaut; Otto, Sijbren; Ng, Yiu‐Fai; Bond, Andrew D.; Sanders, Jeremy K. M.

doi:10.1002/anie.200353075

Cited by 162 publications

(53 citation statements)

References 37 publications

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“…[2]Catenanes C7 and C8 wereo btained in overall yields of about 50 %a nd 20 %, respectively.I nterestingly,i tw as later found that lithium ions could act as an additional template to strengthen the association between PMI and the DN crown ether through interactions with the carbonyl and ether oxygen atoms, and that am etathesis reaction of compound 12 in the presenceo fc rown ether 1 and LiBr in CH 2 Cl 2 /MeOH (98:2) increasedt he yield of [2]catenane C8 to about 60 %. [40] In 2008, Stoddart and co-workers reported the assembly of bistable [2]catenane C9,w hichf eaturedb oth ab ipyridinium dicationa nd an NDI unit as p-acceptors, in which the p-rich DN crowne ther (1)w as found to be stationed at both p-deficient units in ar oughly 1:1r atio at thermale quilibrium ( Figure 10). [41] In 2010, Liu and co-workers reported the synthesis of as eries of desymmetrized [2]catenanes that contained differentcombinations of p-acceptors (i.e.,P MI, NDI, and bipyridinium dication) and p-donors (i.e.,H Q, DN, and TTF) as potential molecular machines with multistability.…”

Section: Ndi-basedand Related Hopf Links In Organic Mediamentioning

confidence: 99%

Molecular Links and Knots from Naphthalenediimide: A Balance of Weak Interactions

Au‐Yeung

2019

Chemistry An Asian Journal

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Owing to its unique structural, electronic,s pectroscopic, andr edox properties, naphthalenediimide (NDI) is a versatile buildingblock for the construction of awide variety of supramolecular assemblies with diverses tructures, properties, and functions. In this Minireview,t he synthesis of topologically nontrivial molecular links and knots based on naphthalenediimide-derived building blocks will be discussed. In particular,t he supramolecular forces that contribute to the formation of these molecularl inks andk nots and their interactions will be discussed.[a] A.

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Section: Ndi-basedand Related Hopf Links In Organic Mediamentioning

confidence: 99%

Molecular Links and Knots from Naphthalenediimide: A Balance of Weak Interactions

Au‐Yeung

2019

Chemistry An Asian Journal

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“…The stability of the loop structure was also due to the strong hydrophobic interactions between the aromatic Scheme 14 Schematic representation of the binding modes and the interconversion process between [5]pseudorotaxane and [3]pseudorotaxanes parts of the two MCVs and CB [8], however, it was still dependent on the property of the linker. When the linker used was triethylene glycol, which is less hydrophobic, the loop structure could also be formed.…”

Section: Pseudorotaxanes Based On Bipyridinium Derivatives and Cucurbmentioning

confidence: 99%

“…Based on this property, we designed and synthesized axle molecule 43 in which two MCV units were located at its two ends and one naphthoxy (NP) group was positioned in the middle (Scheme 14). 43 Upon addition of 1.0 equivalent of CB [8], the electron-rich NP and the electron-deficient MCV unit were included into the cavity of CB [8] [3]pseudorotaxane. The addition of base resulted in a reversible switch between the two different pseudorotaxanes.…”

Section: Pseudorotaxanes Based On Bipyridinium Derivatives and Cucurbmentioning

confidence: 99%

Construction and Function of Interpenetrated Molecules Based on the Positively Charged Axle Components

Zhang

Liu

2012

Synlett

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Interpenetrated molecules have attracted increasing attention from chemists not only because of their intriguing architectures and topologies, but also as a result of potential applications in molecular machinery and nanotechnology. In this account we review recent efforts on the construction of interpenetrated molecules based on the molecular recognition toward some positively charged axle components in aqueous or organic medium. We mainly focus on guest molecules containing ammonium, anilinium, and pyridinium groups. The host molecules are cucurbiturils and crown ethers.

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“…[21] Given the donor set and compact nature of the site, Li + , Na + and Zn 2+ were tested for coordination. Only the smallest Li + ion showed binding [22] as evidenced by significant changes in the 1 H NMR spectrum.…”

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confidence: 99%

Molecular Shuttling of a Compact and Rigid H‐Shaped [2]Rotaxane

Zhu

Vukotic

2012

Angewandte Chemie

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Bistable [2]rotaxanes (molecular shuttles) are mechanically interlocked molecules (MIMs) that can be switched between different translational co-conformations in response to an external stimulus. [1] Chemical, electrochemical, and photochemical inputs have been used to control the actions of these systems in solution and some very efficient and sophisticated examples are known, including those that occupy nonequilibrium states and function using a ratchet-type mechanism. [2] Since most [2]rotaxane molecular shuttles are large, flexible molecules with multiple functional groups they operate with efficiency in solution where the interlocked components enjoy a high degree of structural and dynamic freedom. The size and flexibility of the molecular structure are rarely a problem, [3] however, these attributes make them much less practical for highly condensed phases where the size, positional orientation and degree of aggregation of the MIM components are crucial to optimum switching efficiency. [4] To incorporate efficient molecular switches into materials and devices with a high density of functional components, a compact structure with a rigid axle and short, linear track for translational motion would be most desirable. [5] We report herein a compact MIM-based switch with welldefined geometry, rigid backbone, and efficient switching characteristics for future application in highly dense media. Highlights include 1) the development of a new recognition template for [2]pseudorotaxane formation built around a 24membered crown ether wheel and a benzimidazolium axle with extended aromatic substituents, 2) a high yielding, modular synthesis of [2]rotaxane molecular shuttles with a compact and rigid, H-shaped molecular structure, 3) access to three distinct molecular states and corresponding molecular shuttling rates through acid-base chemistry, and 4) control of the rate of molecular shuttling through lithium ion "ferrying" between neutral binding sites. [6] The interaction of dibenzo[24]crown-8 (DB24C8) with the imidazolium (K a = 8 m À1 ) [7] or phenylbenzimidazolium, [1-H] + (K a = 5.0 10 1 m À1 ) cation is weak but this can be drastically increased by adding aromatic groups to the 4-and 7-positions of the benzimidazolium unit. The benzimidazolium salt [2-H][BF 4 ] was synthesized by reacting 4,7-dibromo-2-phenyl-1H-benzimidazole [8] with 2 equivalents of 4-fluorophenylboronic acid under Suzuki coupling conditions followed by protonation with HBF 4 (see the Supporting Information). The 1 H NMR spectrum of a solution comprised of equimolar amounts of [2-H] + and DB24C8 (1.0 10 À3 m, CD 3 CN, 298 K) shows the efficient formation of [2]pseudorotaxane [2-H&DB24C8] + (Figure 1). The association constant of 1.0 10 3 m À1 is two orders of magnitude larger than for simple imidazolium or benzimidazolium derivatives. Significant shifts to higher frequency were observed for the NH (+ 0.73 ppm) and proton a resonances (+ 0.37 ppm) indicating hydrogen-bonding interactions while shifts to lower frequency for peaks b and c on th...

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Lithium‐Templated Synthesis of a Donor–Acceptor Pseudorotaxane and Catenane

Abstract: Simultaneous coordination of an aromatic electron donor and acceptor to lithium leads to the formation of highly stable colored pseudorotaxane complexes (see picture). The lithium templated pseudorotaxane is an effective precursor to a [2]catenane.

Cited by 162 publications

References 37 publications

Molecular Links and Knots from Naphthalenediimide: A Balance of Weak Interactions

Molecular Links and Knots from Naphthalenediimide: A Balance of Weak Interactions

Construction and Function of Interpenetrated Molecules Based on the Positively Charged Axle Components

Molecular Shuttling of a Compact and Rigid H‐Shaped [2]Rotaxane

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