Ureido cytosine and cytosine-containing acrylic copolymers

Zhang, Keren; Chen, Mingtao; Drummey, Kevin J.; Talley, Samantha J.; Anderson, Lindsey; Moore, Robert B.; Long, Timothy Edward

doi:10.1039/c6py01519k

Cited by 26 publications

(44 citation statements)

References 52 publications

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“…S6). Our previous studies also verified the susceptibility of poly(CyA‐ co ‐nBA)s to crosslinking at higher temperatures compared to poly(UCyA‐ co ‐nBA)s through isothermal rheological experiments . The crosslinking was proposed to correlate with the reaction of the pendant amine with the acrylate esters at elevated temperature.…”

Section: Resultssupporting

confidence: 64%

“…Thus, adjusting the chain lengths of the soft and the hard blocks enabled tailoring mechanical properties from rubbery state to glassy state. In addition, an alkylene spacer within the CyA monomer that connects the cytosine substituent to the acrylate backbone offered tunable T g of the CyA outer block and provided mobility for the cytosine module to self‐assemble …”

Section: Resultsmentioning

confidence: 99%

“…). For CyA polymers, the first step in weight loss around 250 °C represented the degradation of the spacer that connects the acrylic backbone and cytosine unit, and the second step comprised the degradation of acrylic backbone . The T d,5 wt % of the CyA polymer decreased with increasing CyA content (Table ) due to the degradation of CyA pendant groups in the first step.…”

Section: Resultsmentioning

confidence: 99%

“…CyA was prepared according to our earlier literature . In a typical triblock copolymer synthesis, a 50‐mL Schlenk flask was charged with difunctional PnBA macro‐CTA (2 g, 0.049 mmol), CyA (1.72 g, 5.56 mmol), AIBN (0.81 mg, 0.0049 mmol), and DMF (14.88 g, 20 wt % solution).…”

Section: Methodsmentioning

confidence: 99%

“…They reported that PPG‐UCyt exhibited polymer‐like behavior and self‐assembled into a well‐ordered lamellar structure in both solution and bulk. Inspired by this work, our group utilized a regioselective Michael‐addition to synthesize novel cytosine and UCyt acrylate monomers and employed free‐radical polymerization to achieve random copolymers containing cytosine or UCyt pedant groups . The incorporation of UCyt into random copolymers resulted in enhanced mechanical performance and better microphase separation than the cytosine‐containing precursors.…”

Section: Introductionmentioning

confidence: 99%

See 4 more Smart Citations

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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Section: Resultssupporting

confidence: 64%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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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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3Dprinting using polyampholyte hydrogel with reversible behavior

Hwang

Chung

et al. 2021

Polymer International

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A polyampholyte (PA) hydrogel is a highly biocompatible hydrogel consisting of physical ionic bonds of anionic and cationic monomers. It has high strength without other chemical crosslinking agents. Physical ionic bonds of PA can be easily broken with NaCl solution; therefore, PA is easy to process because the viscosity of PA can be adjusted simply by changing the concentration of NaCl. In this study, PA hydrogel was applied to a 3D printer of DIW (direct ink write) additive manufacturing. Hydrogel 3D printing equipment was manufactured by mounting a pressure tank and heater. In order to make PA ink for 3D printing, PA was made in powder form first and then dissolved in NaCl solution to adjust to a suitable concentration in consideration of the processing temperature, mechanical properties and viscosity. The printing conditions were optimized to achieve stable operation of 3D printing. The surface of the printed sample was observed through scanning electron microscopy imaging to confirm that the stacked structure was well adhered. Finally, the characteristics of several structures printed using PA ink were investigated with tensile experiments.

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Guanine and cytosine‐containing acrylic supramolecular networks

Liu,

Spiering,

McDonough

et al. 2023

Journal of Polymer Science

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This manuscript describes the synthesis and characterization of guanine and cytosine‐containing supramolecular copolymers, which are inspired from the guanine and cytosine nucleobase pair in deoxyribonucleic acid. Regioselective Michael‐addition allowed the efficient installation of the nucleobases on acrylate‐containing monomers, which enabled the preparation of a series of nucleobase‐functionalized acrylate and n‐butyl acrylate copolymers using conventional free radical copolymerization. Guanine‐containing copolymers exhibited superior thermal properties, thermomechanical performance, and more defined morphological structure than cytosine‐containing copolymer analogs due to the relatively strong guanine self‐association, thus expanding the potential applications for mechanically reinforced polymeric networks. Blending guanine‐ and cytosine‐containing copolymers formed a supramolecular structure through multiple hydrogen bonding between guanine and cytosine units. The supramolecular blend exhibited intermediate thermomechanical and morphological properties, which suggested that guanine and cytosine units were not fully associated in the random copolymer composition. This work provides valuable fundamental understanding of structure–property‐morphology relationships in acrylic copolymers with the presence of guanine‐cytosine self‐ and complementary interactions, suggesting new understanding in supramolecular design for enhanced mechanical and morphological properties.

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Ureido cytosine and cytosine-containing acrylic copolymers

Abstract: Ureido-cytosine pendant groups contributed to random acrylic copolymers with enhanced thermomechanical performance, well-defined morphologies, and reduced water uptake.

Cited by 26 publications

References 52 publications

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

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

3Dprinting using polyampholyte hydrogel with reversible behavior

Guanine and cytosine‐containing acrylic supramolecular networks

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