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Glink, Peter T.; Oliva, Ana I.; Stoddart, J. Fraser; White, Andrew J. P.; Williams, David J.

doi:10.1002/1521-3757(20010518)113:10<1922::aid-ange1922>3.3.co;2-k

Cited by 36 publications

(68 citation statements)

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“…3). Other attractive dynamic covalent systems involve transacetalization that goes via transesterification under basic conditions, formal metathesis under acidic conditions (34), and imine formation/exchange (35)(36)(37).…”

Section: Resultsmentioning

confidence: 99%

Chemical mimicry of viral capsid self-assembly

Olson

Keinan

2007

Proc. Natl. Acad. Sci. U.S.A.

101

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Stable structures of icosahedral symmetry can serve numerous functional roles, including chemical microencapsulation and delivery of drugs and biomolecules, epitope presentation to allow for an efficient immunization process, synthesis of nanoparticles of uniform size, observation of encapsulated reactive intermediates, formation of structural elements for supramolecular constructs, and molecular computing. By examining physical models of spherical virus assembly we have arrived at a general synthetic strategy for producing chemical capsids at size scales between fullerenes and spherical viruses. Such capsids can be formed by self-assembly from a class of molecules developed from a symmetric pentagonal core. By designing chemical complementarity into the five interface edges of the molecule, we can produce self-assembling stable structures of icosahedral symmetry. We considered three different binding mechanisms: hydrogen bonding, metal binding, and formation of disulfide bonds. These structures can be designed to assemble and disassemble under controlled environmental conditions. We have conducted molecular dynamics simulation on a class of corannulene-based molecules to demonstrate the characteristics of self-assembly and to aid in the design of the molecular subunits. The edge complementarities can be of diverse structure, and they need not reflect the fivefold symmetry of the molecular core. Thus, self-assembling capsids formed from coded subunits can serve as addressable nanocontainers or custom-made structural elements.corannulene ͉ icosahedral capsids ͉ molecular containers ͉ physical modeling ͉ nanotechnology

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Section: Resultsmentioning

confidence: 99%

Chemical mimicry of viral capsid self-assembly

Olson

Keinan

2007

Proc. Natl. Acad. Sci. U.S.A.

101

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“…46. All of the other starting materials are commercially available from Aldrich (St. Louis, MO) or VWR (West Chester, PA) and were used as received.…”

Section: Methodsmentioning

confidence: 99%

“…We have reported (see refs. [46][47][48][49] an example of such a template-directed synthesis of linear and branched [n]rotaxanes (n ϭ 2-4) by employing dynamic covalent chemistry in the form of reversible imine formation ( Fig. 2A).…”

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confidence: 99%

Efficient production of [ n ]rotaxanes by using template-directed clipping reactions

Leung

Stoddart

2007

Proc. Natl. Acad. Sci. U.S.A.

Self Cite

119

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In this article, we report on the efficient synthesis of well defined, homogeneous [n]rotaxanes (n up to 11) by a template-directed thermodynamic clipping approach. By employing dynamic covalent chemistry in the form of reversible imine bond formation, [ dynamic covalent chemistry ͉ molecular recognition ͉ polyrotaxanes ͉ self-assembly ͉ template-directed synthesis M echanically interlocked and knotted compounds, such as rotaxanes (1-5), catenanes (6-10), suitanes (11, 12), trefoil knots (13-17), , and Solomon knots (21), represent challenging synthetic goals that have nevertheless been realized. These molecular compounds are usually synthesized by a template-directed approach (22) that depends on molecular recognition and self-assembly processes. Recently, their potential applications as molecular switches for nanoelectronics (23, 24) and molecular actuators for constructing artificial muscles (25), for fabricating smart surface materials (26), and for controlling the nanoscale release of molecules trapped in mesoporous silica (27)(28)(29) were demonstrated. Polyrotaxanes and well defined, homogeneous oligorotaxanes, in which the recognition sites on a dumbbell (an axle terminated by bulky stoppers) are encircled by large rings or macrocycles (wheels) by dint of molecular recognition, have become (30-36) one of the most intensively investigated subjects in mechanical chemistry. A general synthetic method for making rotaxanes, namely, the ''threading-followed-by-stoppering'' approach (Fig. 1, method A), involves (30-32) several macrocycles. First, the macrocycles are threaded onto oligomeric or polymeric axles carrying recognition sites at prescribed intervals along the axles to form pseudorotaxanes, then both ends of the axles are stoppered with bulky groups. Although this approach is relatively simple, it does not provide complete control over the number of threaded macrocycles, that is, the rings or beads are often not threaded onto all of the available recognition sites on the axles. Alternatively, a template-directed ''clipping'' approach (Fig. 1, method B), in which the macrocycles are formed from acyclic precursors in the presence of templating recognition sites on the dumbbells, has provided (33-36) a versatile means for the construction of some lower-order rotaxanes. Nonetheless, the efficient synthesis of well defined, homogeneous, higher-order polyrotaxanes continues to be a challenge to synthetic chemists.Recently, dynamic covalent chemistry (37-40), exemplified by reversible imine formation (41, 42), metal-ligand exchange (43), and olefin metathesis (44, 45), has been demonstrated to be an effective tool for the preparation of various exotic mechanically interlocked molecular compounds. It has been found that, in the presence of an appropriate template, one of the possible compounds in the dynamic library, after mixing the different components, can be amplified to give the thermodynamically most stable product. We have reported (see refs. 46-49) an example of such a template-directed synthesis of ...

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“…Since the formation of products occurs under thermodynamic control, product distributions depend only on the relative stabilities of the final products. The dynamic covalent chemistry involved in this system, is the highly efficient clipping 42 of a diamine and a dialdehyde to form a Fig. 4 (a) An early example of an a-cyclodextrin-based polyrotaxane, in which a polyethylene glycol chain acts 36 as the thread and the terminal 2,4-dinitrophenyl groups serve as the stoppers; (b) the chemical structure of a b-cyclodextrin-threaded conjugated polyrotaxane which represents 37 an insulated molecular wire.…”

Section: Oligomeric and Polymeric Main-chain [N]rotaxanesmentioning

confidence: 99%

Mechanically bonded macromolecules

et al. 2010

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Mechanically bonded macromolecules constitute a class of challenging synthetic targets in polymer science. The controllable intramolecular motions of mechanical bonds, in combination with the processability and useful physical and mechanical properties of macromolecules, ultimately ensure their potential for applications in materials science, nanotechnology and medicine. This tutorial review describes the syntheses and properties of a library of diverse mechanically bonded macromolecules, which covers (i) main-chain, side-chain, bridged, and pendant oligo/polycatenanes, (ii) main-chain oligo/polyrotaxanes, (iii) poly[c2]daisy chains, and finally (iv) mechanically interlocked dendrimers. A variety of highly efficient synthetic protocols-including template-directed assembly, step-growth polymerisation, quantitative conjugation, etc.-were employed in the construction of these mechanically interlocked architectures. Some of these structures, i.e., side-chain polycatenanes and poly[c2]daisy chains, undergo controllable molecular switching in a manner similar to their small molecular counterparts. The challenges posed by the syntheses of polycatenanes and polyrotaxanes with high molecular weights are contemplated.

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Cited by 36 publications

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Chemical mimicry of viral capsid self-assembly

Chemical mimicry of viral capsid self-assembly

Efficient production of [ n ]rotaxanes by using template-directed clipping reactions

Mechanically bonded macromolecules

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