Supramolecular polymerization of a ureidopyrimidinone‐based [2]catenane prepared <i>via</i> ring‐closing metathesis

Teunissen, Abraham J. P.; Berrocal, José Augusto; Corbet, Christiaan; Meijer, E. W.

doi:10.1002/pola.28694

Cited by 6 publications

(6 citation statements)

References 46 publications

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“…The introduction of additional metal centers, as well as various functional groups, around Sauvage’s Cu(I)-templating phenanthroline core was expected to endow the resulting interlocked compounds with unique properties. By incorporating metal porphyrins and C 60 into Sauvage-type [2]catenanes, a series of electron donor/acceptor systems were assembled. , A Cu(I) [2]catenane functionalized with the potentially quadruple-hydrogen-bonding ureidopyrimidinone (Upy) motif was also described, which allowed supramolecular polymerization of the resulting catenane compound via Upy–Upy dimerization …”

Section: Hopf Linksmentioning

confidence: 99%

Coordination-Directed Construction of Molecular Links

et al. 2020

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Since the emergence of the concept of chemical topology, interlocked molecular assemblies have graduated from academic curiosities and poorly defined species to become synthetic realities. Coordination-directed synthesis provides powerful, diverse, and increasingly sophisticated protocols for accessing interlocked molecules. Originally, metal ions were employed solely as templates to gather and position building blocks in entwined or threaded arrangements. Recently, metal centers have increasingly featured within the backbones of the integral structural elements, which in turn use noncovalent interactions to self-assemble into intricate topologies. By outlining ingenious recent examples as well as seminal classic cases, this Review focuses on the role of metal−ligand paradigms in assembling molecular links. In addition, the ever-evolving approaches to efficient assembly, the structural features of the resulting architectures, and their prospects for the future are also presented.

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Section: Hopf Linksmentioning

confidence: 99%

Coordination-Directed Construction of Molecular Links

et al. 2020

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“…In an effort to address the weak association associated with the aforementioned dimeric hydrogen bonding system for nucleobase derivatives, Hailes and coworkers reported a ureidofunctionalized cytosine that is able to form strong selfcomplementary quadruple hydrogen bonding (QHB) with a dimerization constant (K a > 9 × 10 6 M −1 in deuterated benzene) near the previously reported ureido-pyrimidone module in their seminal work. [24][25][26][27] Reaction of a cytosine with an isocyanate readily allows the formation of an ureido-cytosine (UCyt), which dimerizes through a stable donor-donor-acceptor-acceptor hydrogen bonding array. Since then, UCyt has attracted increasing attention for the synthesis of supramolecular polymers, where the UCyt end groups served as molecular bridges to link telechelic oligomers into supramolecular polymers.…”

mentioning

confidence: 99%

Quadruple hydrogen bonding containing supramolecular thermoplastic elastomers: Mechanical and morphological correlations

Chen

Zhang

Talley

et al. 2018

J. Polym. Sci. Part A: Polym. Chem.

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We report the design of bioinspired, reversible supramolecular thermoplastic elastomers (TPEs) functionalized with ureido‐cytosine (UCyt) complementary quadruple hydrogen bonding (QHB) sites. The polymer contained a soft poly(n‐butyl acrylate) central block that imparted flexibility and two external, hard nucleobase‐containing blocks that contributed to structural integrity. In addition, the hard block with pendant QHB motifs served as efficient physical crosslinks to further enhance the thermomechanical performance, where the polymer service window extended up to 30 °C higher compared to the controls that bear dimeric hydrogen bonding units. The resulting UCyt copolymers also exhibited improved surface and bulk morphology, which self‐assembled into well‐ordered lamellar microstructures. Moreover, the polymer displayed an unexpected moisture‐resistant property with less than 1 wt % equilibrium moisture uptake even at 95% relatively humidity, which presumably correlated with its well‐ordered and densely‐packed morphology facilitated by strong hydrogen bonding. Variable temperature Fourier‐transform infrared spectroscopy experiments further confirmed the thermoreversibility of hydrogen bonding, indicating melt‐processablility and recyclability of the polymer. These physical properties verified quadruple bonding dominated behavior, and structure–property–morphology relationships suggest key design parameters for future TPEs. © 2018 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2019, 57, 13–23

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“…16). 121 The resulting self-complementary ditopic monomer polymerizes through intermolecular quadruple hydrogen bonding to create an SP with alternating hydrogen bonding and mechanical bonding. Interestingly, polymeric structures were only observed by DLS when the Sauvage linkage was metalated.…”

Section: Topological Chirality: Chiral Catenanesmentioning

confidence: 99%

Supramolecular polymerization of chiral molecules devoid of chiral centers

Henderson

Castellano

2020

Polymer International

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The iterative association of monomer units through noncovalent interactions often leads to chiral supramolecular polymers. Monomers comprising these materials can be further divided into those with chiral centers and those without. The latter class is often less studied but attractive since it features monomer designs with chirality at the core rather than the periphery of the molecules. In this mini-review, we summarize the existing strategies to construct supramolecular polymers from chiral molecules with no chiral centers and offer perspectives on fundamental trends and differences between them and their counterparts with chiral centers.

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Supramolecular polymerization of a ureidopyrimidinone‐based [2]catenane prepared via ring‐closing metathesis

Cited by 6 publications

References 46 publications

Coordination-Directed Construction of Molecular Links

Coordination-Directed Construction of Molecular Links

Quadruple hydrogen bonding containing supramolecular thermoplastic elastomers: Mechanical and morphological correlations

Supramolecular polymerization of chiral molecules devoid of chiral centers

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