Journal of the American Chemical Society
Page 8 of 18
1
2
3
4
(14) Xu, J.; Li, X.; Li, X.; Li, B.; Wu, L.; Li, W.; Xie, X.; Xue, R.
Supramolecular Copolymerization of Short Peptides and
Polyoxometalates: toward the Fabrication of Underwater Adhesives.
Biomacromolecules 2017, 18, 3524–3530.
Supporting Information
The Supporting Information is available free of charge on the
ACS Publications website.
(15) Yang, J.; Bai, R.; Suo, Z. Topological Adhesion of Wet Materials.
Adv. Mater. 2018, 30, 1800671.
5
6
7
8
Experimental procedures, characterization and NMR spectra for
obtained compounds and other materials (PDF).
(16) Matos-Pérez, C. R.; White, J. D.; Wilker, J. J. Polymer Composition
and Substrate Influences on the Adhesive Bonding of a Biomimetic,
Cross-Linking Polymer. J. Am. Chem. Soc. 2012, 134, 9498–9505.
(17) Seo, S.; Das, S.; Zalicki, P. J.; Mirshafian, R.; Eisenbach, C. D.;
Israelachvili, J. N.; Waite, J. H.; Ahn, B. K. Microphase Behavior and
Enhanced Wet-Cohesion of Synthetic Copolyampholytes Inspired by a
Mussel Foot Protein. J. Am. Chem. Soc. 2015, 137, 9214−9217.
(18) Ahn, B. K. Perspectives on Mussel-Inspired Wet Adhesion. J. Am.
Chem. Soc. 2017, 139, 10166−10171.
(19) Hofman, A. H.; van Hees, I. A.; Yang, J.; Kamperman, M.
Bioinspired Underwater Adhesives by Using the Supramolecular Toolbox.
Adv. Mater. 2018, 30, 1704640.
(20) Pinnaratip, R.; Bhuiyan, M. S. A.; Meyers, K.; Rajachar, R. M.; Lee,
B. P. Multifunctional Biomedical Adhesives. Adv. Healthcare Mater.
2019, 8, 1801568.
(21) Degen, G. D.; Stow, P. R.; Lewis, R. B.; Eguiluz, R. C. A.; Valois,
E.; Kristiansen, K.; Butler, A.; Israelachvili, J. N. Impact of Molecular
Architecture and Adsorption Density on Adhesion of Mussel-Inspired
Surface Primers with Catechol-Cation Synergy. J. Am. Chem. Soc. 2019,
141, 18673−18681.
(22) Wilker, J. J. Self-Healing Polymers: Sticky when Wet. Nat. Mater.
2014, 13, 849–850.
(23) North, M. A.; Del Grosso, C. A.; Wilker, J. J. High Strength
Underwater Bonding with Polymer Mimics of Mussel Adhesive Proteins.
ACS Appl. Mater. Interfaces 2017, 9, 7866−7872.
(24) Shao, H.; Stewart, R. J. Biomimetic Underwater Adhesives with
Environmentally Triggered Setting Mechanisms. Adv. Mater. 2010, 22,
729–733.
(25) Jones, J. P.; Sima, M.; O’Hara, R. G.; Stewart, R. J. Water-Borne
Endovascular Embolics Inspired by the Undersea Adhesive of Marine
Sandcastle Worms. Adv. Healthcare Mater. 2016, 5, 795–801.
(26) Xu, Y.; Liu, Q.; Narayanan, A.; Jain, D.; Dhinojwala, A.; Joy, A.
Mussel-Inspired Polyesters with Aliphatic Pendant Groups Demonstrate
the Importance of Hydrophobicity in Underwater Adhesion. Adv. Mater.
Interfaces 2017, 4, 1700506.
(27) Narayanan, A.; Kaur, S.; Peng, C.; Debnath, D.; Mishra, K.; Liu, Q.;
Dhinojwala, A.; Joy, A. Viscosity Attunes the Adhesion of Bioinspired
Low Modulus Polyester Adhesive Sealants to Wet Tissues.
Biomacromolecules 2019, 20, 2577–2586.
(28) Lee, B. P.; Konst, S. Novel Hydrogel Actuator Inspired by
Reversible Mussel Adhesive Protein Chemistry. Adv. Mater. 2014, 26,
3415–3419.
(29) Narkar, A. R.; Barker, B.; Clisch, M.; Jiang, J.; Lee, B. P. pH
Responsive and Oxidation Resistant Wet Adhesive Based on Reversible
Catechol-Boronate Complexation. Chem. Mater. 2016, 28, 5432–5439.
(30) Courtois, J.; Baroudi, I.; Nouvel, N.; Degrandi, E.; Pensec, S.;
Ducouret, G.; Chanéac, C.; Bouteiller, L.; Creton, C. Supramolecular Soft
Adhesive Materials. Adv. Funct. Mater. 2010, 20, 1803–1811.
(31) Maier, G. P.; Rapp, M. V.; Waite, J. H.; Israelachvili, J. N.; Butler,
A. Adaptive Synergy between Catechol and lysine Promotes Wet
Adhesion by Surface Salt Displacement. Science 2015, 349, 628–632.
(32) Wu, Z.; Ji, C.; Zhao, X.; Han, Y.; Müllen, K.; Pan, K.; Yin, M.
Green-Light-Triggered Phase Transition of Azobenzene Derivatives
toward Reversible Adhesives. J. Am. Chem. Soc. 2019, 141, 7385–7390.
(33) Niu, Z.; Gibson, H. W. Polycatenanes. Chem. Rev. 2009, 109, 6024–
6046.
(34) Zhou, H.; Xue, C.; Weis, P.; Suzuki, Y.; Huang, S.; Koynov, K.;
Auernhammer, G. K.; Berger, R.; Butt, H.-J.; Wu, S. Photoswitching of
Glass Transition Temperatures of Azobenzene-Containing Polymers
Induces Reversible Solid-to-Liquid Transitions. Nat. Chem. 2017, 9, 145–
151.
(35) Zhang, Q.; Shi, C.-Y.; Qu, D-H.; Long, Y.-T.; Feringa, B. L.; Tian,
H. Exploring a Naturally Tailored Small Molecule for Stretchable, Self-
Healing, and Adhesive Supramolecular Polymers. Sci. Adv. 2018, 4, No.
eaat8192.
AUTHOR INFORMATION
Corresponding Author
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60
* dongsy@hnu.edu.cn
* zhaogai@nuaa.edu.cn
ORCID
Shengyi Dong: 0000-0002-8640-537X
Notes
The authors declare no competing financial interests.
ACKNOWLEDGMENT
This work was supported by National Natural Science Foundation
of China (21704024), Huxiang Young Talent Program from
Hunan Province (2018RS3036), and the Fundamental Research
Funds for the Central Universities from Hunan University.
REFERENCES
(1) Heinzmann, C.; Weder, C.; de Espinosa, L. M. Supramolecular
Polymer Adhesives: Advanced Materials Inspired by Nature. Chem. Soc.
Rev. 2016, 45, 342–358.
(2) Ji, X.; Ahmed, M.; Long, L.; Khashab, N. M.; Huang, F.; Sessler, J. L.
Adhesive Supramolecular Polymeric Materials Constructed from
Macrocycle-Based Host-Guest Interactions. Chem. Soc. Rev. 2019, 48,
2682–2697.
(3) Gao, Z.; Yue, C.; Cao, H.; Wang, X.; Zhu, X.; Lin, R. Preparation
and Formaldehyde Emission and Bonding Performance of Novel Modified
Urea-Formaldehyde Resin Adhesive. Adv. Mater. Res. 2012, 490–495,
3476–3480.
(4) Zhu, Y.; Di, B.; Chen, H.; Wang, X.; Tian, Y. In Situ Synthesis of
Novel Biomass Lignin/Silica Based Epoxy Resin Adhesive from
Renewable Resources at Different pHs. J. Adhes. Sci. Technol. 2019, 33,
1806–1820.
(5) Parija, S.; Misra, M.; Mohanty, A. K. Studies of Natural Gum
Adhesive Extracts: an Overview. J. Macromol. Sci., Polym. Rev. 2001, 41,
175–197.
(6) Kim, J. H.; Min, H. J.; Park, K.; Kim, J. Preparation and Evaluation
of a Cosmetic Adhesive Containing Guar Gum. Korean J. Chem. Eng.
2017, 34, 2236–2240.
(7) Liu, J.; Scherman, O. A. Cucurbit[n]uril Supramolecular Hydrogel
Networks as Tough and Healable Adhesives. Adv. Funct. Mater. 2018, 28,
1800848.
(8) Zhang, F.; Xiong, L.; Ai, Y.; Liang, Z.; Liang, Q. Stretchable
Multiresponsive Hydrogel with Actuatable, Shape Memory, and Self-
Healing Properties. Adv. Sci. 2018, 5, No. 1800450.
(9) Gan, D.; Xing, W.; Jiang, L.; Fang, J.; Zhao, C.; Ren, F.; Fang, L.;
Wang, K.; Lu, X. Plant-Inspired Adhesive and Tough Hydrogel Based on
Ag-Lignin Nanoparticles-Triggered Dynamic Redox Catechol Chemistry.
Nat. Commun. 2019, 10, 1487–1497.
(10) Yang, J.; Bai, R.; Chen, B.; Suo, Z. Hydrogel Adhesion: A
Supramolecular Synergy of Chemistry, Topology, and Mechanics. Adv.
Funct. Mater. 2020, 30, 1901693.
(11) Stewart, R. J.; Ransom, T. C.; Hlady, V. Natural Underwater
Adhesives. J. Polym. Sci. B 2011, 49, 757–771.
(12) Stewart, R. J. Protein-Based Underwater Adhesives and the
Prospects for Their Biotechnological Production. Appl. Microbiol.
Biotechnol. 2011, 89, 27–33.
(13) Ahn, Y.; Jang, Y.; Selvapalam, N.; Yun, G.; Kim, K.
Supramolecular Velcro for Reversible Underwater Adhesion. Angew.
Chem., Int. Ed. 2013, 52, 3140–3144.
(36) Dong, S.; Leng, J.; Feng, Y.; Liu, M.; Stackhouse, C. J.; Schönhals,
A.; Chiappisi, L.; Gao, L.; Chen, W.; Shang, J.; Jin, L.; Qi, Z.; Schalley, C.
ACS Paragon Plus Environment