Synthesis of Triazole‐linked Homonucleoside Polymers through Topochemical Azide–Alkyne Cycloaddition

Pathigoolla, Atchutarao; Sureshan, Kana M.

doi:10.1002/ange.201404797

Cited by 21 publications

(1 citation statement)

References 77 publications

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“…Topochemical polymerization refers to the transformation of crystallized, solid-state monomers into macromolecular species. , Early investigations into linear solid-state polymerization led by Schmidt, Wegner, − Heyman, Adler, Morawetz, , Kitanishi, and Fischer laid a groundwork understanding of monomer design and chemical approaches for topological polymerization. ,, In nearly all cases, topochemical polymerization is performed by first crystallizing monomeric species and then irradiating the crystals with light, although recent work on azide–alkyne cycloaddition topochemical polymerization has shown that other strategies may be viable. − Molecular preorganization guides the structural regularity of the resultant macromolecular species, which generally leads to highly regular polymers. Similarly, the crystallization of planar monomers into lamellar sheets enables the synthesis of large-area macromolecular sheets (Figure ).…”

Section: Two-dimensional Polymerization Methodsmentioning

confidence: 99%

Two-Dimensional Polymers and Polymerizations

et al. 2021

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Synthetic chemists have developed robust methods to synthesize discrete molecules, linear and branched polymers, and disordered cross-linked networks. However, two-dimensional polymers (2DPs) prepared from designed monomers have been long missing from these capabilities, both as objects of chemical synthesis and in nature. Recently, new polymerization strategies and characterization methods have enabled the unambiguous realization of covalently linked macromolecular sheets. Here we review 2DPs and 2D polymerization methods. Three predominant 2D polymerization strategies have emerged to date, which produce 2DPs either as monolayers or multilayer assemblies. We discuss the fundamental understanding and scope of each of these approaches, including: the bond-forming reactions used, the synthetic diversity of 2DPs prepared, their multilayer stacking behaviors, nanoscale and mesoscale structures, and macroscale morphologies. Additionally, we describe the analytical tools currently available to characterize 2DPs in their various isolated forms. Finally, we review emergent 2DP properties and the potential applications of planar macromolecules. Throughout, we highlight achievements in 2D polymerization and identify opportunities for continued study.

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Section: Two-dimensional Polymerization Methodsmentioning

confidence: 99%

Two-Dimensional Polymers and Polymerizations

et al. 2021

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Semiconducting Fabrics by In Situ Topochemical Synthesis of Polydiacetylene: A New Dimension to the Use of Organogels

et al. 2015

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Ad iyne functionalized4 ,6-O-benzylidene b-dgalactopyranoside gelator,w hichc an align its diyne motifs upon self-assembly (gelation) have been synthesized. The organogel formed by this gelator undergoes topochemical polymerization to polydiacetylene (PDA) under photoirradiation. This strategically designed gelator has been used to make semi-conducting fabrics.B yd eveloping the organogel on the fabrics,t he gelator molecules were made not only to selfassemble on the fibers,b ut also to adhere to fabrics through hydrogen bonding.U Vi rradiation of the gel-coated fabric/ fiber resulted in the formation of PDAo nf ibers.T he benzylidene motif could be deprotected to get PDAw ith pendant free sugars that strongly bind to the cotton fibrils through multiple hydrogen bonds.Conductivity measurements revealed the semiconducting nature of these fabrics.

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Tunable Mechanical Response from a Crystal Undergoing Topochemical Dimerization: Instant Explosion at a Faster Rate and Chemical Storage of a Harvestable Explosion at a Slower Rate

Ravi

Sureshan

2018

Angewandte Chemie

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Strain developed in crystals in response to stimuli causes mechanical response.Methods to tune such mechanical response is important for practical applications.C rystals of am onomer having azide and alkyne units pre-organized in ar eady-to-react orientation, undergo thermal topochemical dimerization and show rate-dependent mechanical response. When the reaction rate is fast, the crystals explode violently. When the reaction rate is slow,t he crystals absorb water from the surroundings contemporaneously with the reaction to form the dimer-hydrate in as ingle-crystal-to-single-crystal (SCSC) manner.C rystals of the dimer-hydrate upon dehydration also undergo explosion. Thus,a ts lowr eaction rate,t he strain gets stored in crystals by hydration and the explosion can be harvested, at will, by dehydration. Use of this rate-dependent explosion in the automatic activation of ar emedial electrical circuit in case of as udden rise in temperature has been demonstrated.

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Synthesis of Triazole‐linked Homonucleoside Polymers through Topochemical Azide–Alkyne Cycloaddition

Cited by 21 publications

References 77 publications

Two-Dimensional Polymers and Polymerizations

Two-Dimensional Polymers and Polymerizations

Semiconducting Fabrics by In Situ Topochemical Synthesis of Polydiacetylene: A New Dimension to the Use of Organogels

Tunable Mechanical Response from a Crystal Undergoing Topochemical Dimerization: Instant Explosion at a Faster Rate and Chemical Storage of a Harvestable Explosion at a Slower Rate

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