Reinforced double-threaded slide-ring networks for accelerated hydrogel discovery and 3D printing

Tang, Miao; Zheng, Dan; Samanta, Jayanta; Tsai, Esther H. R.; Qiu, Huibin; Read, Jacquelyne A.; Ke, Chenfeng

doi:10.1016/j.chempr.2023.07.020

Reinforced double-threaded slide-ring networks for accelerated hydrogel discovery and 3D printing

Journal Article · Wed Aug 23 00:00:00 EDT 2023 · Chem

DOI:https://doi.org/10.1016/j.chempr.2023.07.020· OSTI ID:2352187

Tang, Miao ^[1]; Zheng, Dan ^[1]; Samanta, Jayanta ^[1]; ^[2]; Qiu, Huibin ^[3]; Read, Jacquelyne A. ^[1]; ^[1]

Dartmouth College, Hanover, NH (United States)
Brookhaven National Laboratory (BNL), Upton, NY (United States). Center for Functional Nanomaterials (CFN)
Shanghai Jiao Tong Univ. (China)

Traditionally, slide-ring gels are stretchable but soft as a result of an elasticity-stretchability trade-off. Herein, we introduce a new approach to breaking this trade-off and creating reinforced slide-ring networks with mobile crosslinkers. Our approach involves the construction of a polyethylene glycol double-threaded γ-cyclodextrin-based pro-slide-ring crosslinker that serves as a modular component for 3D printing and copolymerization. The resulting crystalline-domain-reinforced slide-ring hydrogels, or CrysDoS-gels, exhibit both high elasticity and high stretchability. The modular synthesis allows for high-throughput synthesis of CrysDoS-gels, generating a large amount of data for structure-property analysis. Here, by employing data science techniques, such as machine learning and linear regression, not only were we able to identify which chemical components influence the mechanical properties of CrysDoS-gels, but this analysis also aided in the discovery of better-performing CrysDoS-gels. Finally, we demonstrate the potential application of the newly discovered CrysDoS-gels as sensing devices by 3D printing them as stress sensors with high sensitivity and a broad detection range.

View Accepted Manuscript (DOE)

Research Organization:: Brookhaven National Laboratory (BNL), Upton, NY (United States)

Sponsoring Organization:: National Science Foundation (NSF); USDOE Office of Science (SC), Basic Energy Sciences (BES). Scientific User Facilities (SUF)

Grant/Contract Number:: SC0012704; SC0022267

OSTI ID:: 2352187

Report Number(s):: BNL--225613-2024-JAAM

Journal Information:: Chem, Journal Name: Chem Journal Issue: 12 Vol. 9; ISSN 2451-9294

Publisher:: Cell PressCopyright Statement

Country of Publication:: United States

Language:: English

References (55)

The Polyrotaxane Gel: A Topological Gel by Figure-of-Eight Cross-links Okumura, Y.; Ito, K. Advanced Materials, Vol. 13, Issue 7 https://doi.org/10.1002/1521-4095(200104)13:7<485::AID-ADMA485>3.0.CO;2-T	journal	April 2001
Double-Network Hydrogels with Extremely High Mechanical Strength Gong, J. P.; Katsuyama, Y.; Kurokawa, T. Advanced Materials, Vol. 15, Issue 14 https://doi.org/10.1002/adma.200304907	journal	July 2003
A Bioinspired Mineral Hydrogel as a Self-Healable, Mechanically Adaptable Ionic Skin for Highly Sensitive Pressure Sensing Lei, Zhouyue; Wang, Quankang; Sun, Shengtong Advanced Materials, Vol. 29, Issue 22 https://doi.org/10.1002/adma.201700321	journal	April 2017
Catalytic Enantiodifferentiating Photocyclodimerization of 2-Anthracenecarboxylic Acid Mediated by a Non-Sensitizing Chiral Metallosupramolecular Host Ke, Chenfeng; Yang, Cheng; Mori, Tadashi Angewandte Chemie International Edition, Vol. 48, Issue 36 https://doi.org/10.1002/anie.200902911	journal	August 2009
Ring Shuttling Controls Macroscopic Motion in a Three-Dimensional Printed Polyrotaxane Monolith Lin, Qianming; Hou, Xisen; Ke, Chenfeng Angewandte Chemie International Edition, Vol. 56, Issue 16 https://doi.org/10.1002/anie.201612440	journal	March 2017
Decoupled Thermo‐ and pH‐Responsive Hydrogel Microspheres Cross‐Linked by Rotaxane Networks Kureha, Takuma; Aoki, Daichi; Hiroshige, Seina Angewandte Chemie International Edition, Vol. 56, Issue 48 https://doi.org/10.1002/anie.201709633	journal	October 2017
Polymer Networks: From Plastics and Gels to Porous Frameworks Gu, Yuwei; Zhao, Julia; Johnson, Jeremiah A. Angewandte Chemie International Edition, Vol. 59, Issue 13 https://doi.org/10.1002/anie.201902900	journal	March 2020
An Integrated Design of a Polypseudorotaxane‐Based Sea Cucumber Mimic Li, Longyu; Lin, Qianming; Tang, Miao Angewandte Chemie International Edition, Vol. 60, Issue 18 https://doi.org/10.1002/anie.202017019	journal	March 2021
Solubilization of Polycyclic Aromatics in Water by γ-Cyclodextrin Derivatives Wang, Hai Ming; Wenz, Gerhard Chemistry - An Asian Journal, Vol. 6, Issue 9 https://doi.org/10.1002/asia.201100217	journal	July 2011
Structural Versatility in Slide-Ring Gels: Influence of Co-Threaded Cyclodextrin Spacers Murakami, Takuya; Schmidt, Bernhard V. K. J.; Brown, Hugh R. Journal of Polymer Science Part A: Polymer Chemistry, Vol. 55, Issue 7 https://doi.org/10.1002/pola.28490	journal	January 2017
Wound treatment with Sorbsan — an alginate fibre dressing Gilchrist, T.; Martin, A. Biomaterials, Vol. 4, Issue 4 https://doi.org/10.1016/0142-9612(83)90036-4	journal	October 1983
Soft contact lens polymers: an evolution Nicolson, Paul C.; Vogt, Jürgen Biomaterials, Vol. 22, Issue 24 https://doi.org/10.1016/S0142-9612(01)00165-X	journal	December 2001
Hydrogels in pharmaceutical formulations Peppas, N. European Journal of Pharmaceutics and Biopharmaceutics, Vol. 50, Issue 1 https://doi.org/10.1016/S0939-6411(00)00090-4	journal	July 2000
Kinetic trapping of 3D-printable cyclodextrin-based poly(pseudo)rotaxane networks Lin, Qianming; Li, Longyu; Tang, Miao Chem, Vol. 7, Issue 9 https://doi.org/10.1016/j.chempr.2021.06.004	journal	September 2021
Micropatterned elastic ionic polyacrylamide hydrogel for low-voltage capacitive and organic thin-film transistor pressure sensors Yin, Ming-Jie; Yin, Zhigang; Zhang, Yangxi Nano Energy, Vol. 58 https://doi.org/10.1016/j.nanoen.2019.01.032	journal	April 2019
Synthesis of rotaxane cross-linked polymers with supramolecular cross-linkers based on γ-CD and PTHF macromonomers: The effect of the macromonomer structure on the polymer properties Iijima, Keisuke; Aoki, Daisuke; Otsuka, Hideyuki Polymer, Vol. 128 https://doi.org/10.1016/j.polymer.2017.01.024	journal	October 2017
Synthesis and properties of rotaxane-cross-linked polymers using a double-stranded γ-CD-based inclusion complex as a supramolecular cross-linker Jang, Keumhee; Iijima, Keisuke; Koyama, Yasuhito Polymer, Vol. 128 https://doi.org/10.1016/j.polymer.2017.01.062	journal	October 2017
Formation of well-defined supramolecular microstructures consisting of γ-cyclodextrin and polyether —rods, cubes, plates, and nanosheets—guided by guest polymer structure Uenuma, Shuntaro; Maeda, Rina; Yokoyama, Hideaki Polymer, Vol. 179 https://doi.org/10.1016/j.polymer.2019.121689	journal	September 2019
Highly Stretchable and Instantly Recoverable Slide-Ring Gels Consisting of Enzymatically Synthesized Polyrotaxane with Low Host Coverage Jiang, Lan; Liu, Chang; Mayumi, Koichi Chemistry of Materials, Vol. 30, Issue 15 https://doi.org/10.1021/acs.chemmater.8b01208	journal	July 2018
Soft Materials by Design: Unconventional Polymer Networks Give Extreme Properties Zhao, Xuanhe; Chen, Xiaoyu; Yuk, Hyunwoo Chemical Reviews, Vol. 121, Issue 8 https://doi.org/10.1021/acs.chemrev.0c01088	journal	April 2021
Molecular Characterization of Polymer Networks Danielsen, Scott P. O.; Beech, Haley K.; Wang, Shu Chemical Reviews, Vol. 121, Issue 8 https://doi.org/10.1021/acs.chemrev.0c01304	journal	April 2021
One-Pot “Click” Fabrication of Slide-Ring Gels Murakami, Takuya; Schmidt, Bernhard V. K. J.; Brown, Hugh R. Macromolecules, Vol. 48, Issue 21 https://doi.org/10.1021/acs.macromol.5b01713	journal	October 2015
Anisotropic, Flexible Wood Hydrogels and Wrinkled, Electrodeposited Film Electrodes for Highly Sensitive, Wide-Range Pressure Sensing Nie, Kangchen; Wang, Zhaosong; Tang, Ruixin ACS Applied Materials & Interfaces, Vol. 12, Issue 38 https://doi.org/10.1021/acsami.0c13962	journal	September 2020
Capacitive Pressure Sensors Containing Reliefs on Solution-Processable Hydrogel Electrodes Zhou, Hongwei; Wang, Mingcheng; Jin, Xilang ACS Applied Materials & Interfaces, Vol. 13, Issue 1 https://doi.org/10.1021/acsami.0c18355	journal	January 2021
Exploring Structure–Function Relationships of Aryl Pyrrolidine-Based Hydrogen-Bond Donors in Asymmetric Catalysis Using Data-Driven Techniques Samha, Mohammad H.; Wahlman, Julie L. H.; Read, Jacquelyne A. ACS Catalysis, Vol. 12, Issue 24 https://doi.org/10.1021/acscatal.2c04824	journal	November 2022
Deep Reinforcement Learning for Digital Materials Design Sui, Fanping; Guo, Ruiqi; Zhang, Zhizhou ACS Materials Letters, Vol. 3, Issue 10 https://doi.org/10.1021/acsmaterialslett.1c00390	journal	August 2021
Zwitterionic Skins with a Wide Scope of Customizable Functionalities Lei, Zhouyue; Wu, Peiyi ACS Nano, Vol. 12, Issue 12 https://doi.org/10.1021/acsnano.8b08062	journal	November 2018
Cyclodextrin Rotaxanes and Polyrotaxanes Wenz, Gerhard; Han, Bao-Hang; Müller, Axel Chemical Reviews, Vol. 106, Issue 3 https://doi.org/10.1021/cr970027+	journal	February 2006
Machine-Learning-Guided Discovery of ¹⁹F MRI Agents Enabled by Automated Copolymer Synthesis Reis, Marcus; Gusev, Filipp; Taylor, Nicholas G. Journal of the American Chemical Society, Vol. 143, Issue 42 https://doi.org/10.1021/jacs.1c08181	journal	October 2021
Doubly Threaded Slide-Ring Polycatenane Networks Hart, Laura F.; Lenart, William R.; Hertzog, Jerald E. Journal of the American Chemical Society, Vol. 145, Issue 22 https://doi.org/10.1021/jacs.3c02837	journal	May 2023
Double-stranded inclusion complexes of cyclodextrin threaded on poly(ethylene glycol) Harada, Akira; Li, Jun; Kamachi, Mikiharu Nature, Vol. 370, Issue 6485 https://doi.org/10.1038/370126a0	journal	July 1994
Designing hydrogels for controlled drug delivery Li, Jianyu; Mooney, David J. Nature Reviews Materials, Vol. 1, Issue 12 https://doi.org/10.1038/natrevmats.2016.71	journal	October 2016
Highly stretchable and tough hydrogels Sun, Jeong-Yun; Zhao, Xuanhe; Illeperuma, Widusha R. K. Nature, Vol. 489, Issue 7414 https://doi.org/10.1038/nature11409	journal	September 2012
Extremely stretchable thermosensitive hydrogels by introducing slide-ring polyrotaxane cross-linkers and ionic groups into the polymer network Bin Imran, Abu; Esaki, Kenta; Gotoh, Hiroaki Nature Communications, Vol. 5, Issue 1 https://doi.org/10.1038/ncomms6124	journal	October 2014
Novel entropic elasticity of polymeric materials: why is slide-ring gel so soft? Ito, Kohzo Polymer Journal, Vol. 44, Issue 1 https://doi.org/10.1038/pj.2011.85	journal	September 2011
Accelerating amorphous polymer electrolyte screening by learning to reduce errors in molecular dynamics simulated properties Xie, Tian; France-Lanord, Arthur; Wang, Yanming Nature Communications, Vol. 13, Issue 1 https://doi.org/10.1038/s41467-022-30994-1	journal	June 2022
Highly compressible glass-like supramolecular polymer networks Huang, Zehuan; Chen, Xiaoyi; O’Neill, Stephen J. K. Nature Materials, Vol. 21, Issue 1 https://doi.org/10.1038/s41563-021-01124-x	journal	November 2021
Hydrogel ionotronics Yang, Canhui; Suo, Zhigang Nature Reviews Materials, Vol. 3, Issue 6 https://doi.org/10.1038/s41578-018-0018-7	journal	May 2018
Hydrogel microparticles for biomedical applications Daly, Andrew C.; Riley, Lindsay; Segura, Tatiana Nature Reviews Materials, Vol. 5, Issue 1 https://doi.org/10.1038/s41578-019-0148-6	journal	November 2019
Biocompatible, stretchable and mineral PVA–gelatin–nHAP hydrogel for highly sensitive pressure sensors Zhu, Yi; Lu, Weipeng; Guo, Yanchuan RSC Advances, Vol. 8, Issue 65 https://doi.org/10.1039/C8RA06193A	journal	January 2018
Pronounced effects of the densities of threaded rings on the strain-dependent Poisson's ratio of polyrotaxane gels with movable cross-links Tanaka, Akira; Kato, Kazuaki; Ito, Kohzo Soft Matter, Vol. 14, Issue 15 https://doi.org/10.1039/C8SM00257F	journal	January 2018
Highly stretchable, transparent cellulose/PVA composite hydrogel for multiple sensing and triboelectric nanogenerators Wang, Yang; Zhang, Lina; Lu, Ang Journal of Materials Chemistry A, Vol. 8, Issue 28 https://doi.org/10.1039/D0TA02010A	journal	January 2020
Liquid metal-created macroporous composite hydrogels with self-healing ability and multiple sensations as artificial flexible sensors Zhang, Zhixing; Tang, Lin; Chen, Can Journal of Materials Chemistry A, Vol. 9, Issue 2 https://doi.org/10.1039/D0TA09730F	journal	January 2021
Muscle-inspired capacitive tactile sensors with superior sensitivity in an ultra-wide stress range Shen, Xiaoping; Nie, Kangchen; Zheng, Li Journal of Materials Chemistry C, Vol. 8, Issue 17 https://doi.org/10.1039/D0TC00453G	journal	January 2020
Combining machine learning and high-throughput experimentation to discover photocatalytically active organic molecules Li, Xiaobo; Maffettone, Phillip M.; Che, Yu Chemical Science, Vol. 12, Issue 32 https://doi.org/10.1039/D1SC02150H	journal	January 2021
Mechanics of slide-ring gels: novel entropic elasticity of a topological network formed by ring and string Mayumi, Koichi; Tezuka, Masahiko; Bando, Akinori Soft Matter, Vol. 8, Issue 31 https://doi.org/10.1039/c2sm25508a	journal	January 2012
The Scherrer Formula for X-Ray Particle Size Determination Patterson, A. L. Physical Review, Vol. 56, Issue 10 https://doi.org/10.1103/PhysRev.56.978	journal	November 1939
Optically transparent, high-toughness elastomer using a polyrotaxane cross-linker as a molecular pulley Gotoh, Hiroaki; Liu, Chang; Imran, Abu Bin Science Advances, Vol. 4, Issue 10 https://doi.org/10.1126/sciadv.aat7629	journal	October 2018
Accelerating computational discovery of porous solids through improved navigation of energy-structure-function maps Pyzer-Knapp, Edward O.; Chen, Linjiang; Day, Graeme M. Science Advances, Vol. 7, Issue 33 https://doi.org/10.1126/sciadv.abi4763	journal	August 2021
Advances in engineering hydrogels Zhang, Yu Shrike; Khademhosseini, Ali Science, Vol. 356, Issue 6337 https://doi.org/10.1126/science.aaf3627	journal	May 2017
Highly elastic binders integrating polyrotaxanes for silicon microparticle anodes in lithium ion batteries Choi, Sunghun; Kwon, Tae-woo; Coskun, Ali Science, Vol. 357, Issue 6348 https://doi.org/10.1126/science.aal4373	journal	July 2017
Tough hydrogels with rapid self-reinforcement Liu, Chang; Morimoto, Naoya; Jiang, Lan Science, Vol. 372, Issue 6546 https://doi.org/10.1126/science.aaz6694	journal	June 2021
Topological supramolecular network enabled high-conductivity, stretchable organic bioelectronics Jiang, Yuanwen; Zhang, Zhitao; Wang, Yi-Xuan Science, Vol. 375, Issue 6587 https://doi.org/10.1126/science.abj7564	journal	March 2022
Catalytic asymmetric C–H insertion reactions of vinyl carbocations Nistanaki, Sepand K.; Williams, Chloe G.; Wigman, Benjamin Science, Vol. 378, Issue 6624 https://doi.org/10.1126/science.ade5320	journal	December 2022
Tough Double Network Hydrogel and Its Biomedical Applications Nonoyama, Takayuki; Gong, Jian Ping Annual Review of Chemical and Biomolecular Engineering, Vol. 12, Issue 1 https://doi.org/10.1146/annurev-chembioeng-101220-080338	journal	June 2021

Similar Records

3D-printed ketoenamine crosslinked polyrotaxane hydrogels and their mechanochromic responsiveness

Journal Article · Sun Apr 23 20:00:00 EDT 2023 · Polymer Chemistry · OSTI ID:2422125

Hierarchically Templated Synthesis of 3D‐Printed Crosslinked Cyclodextrins for Lycopene Harvesting

Journal Article · Thu Apr 06 20:00:00 EDT 2023 · Small · OSTI ID:1968970

Related Subjects

3D-printing
77 NANOSCIENCE AND NANOTECHNOLOGY
cyclodextrin
double-threaded network
high-throughput synthesis
hydrogel
machine learning
polyrotaxane
slide-ring

Reinforced double-threaded slide-ring networks for accelerated hydrogel discovery and 3D printing

Citation Formats

References (55)

Linked Research (1)

Similar Records

Related Subjects