Hydrogen-Bonded Supramolecular Polymer Adhesives: Straightforward Synthesis and Strong Substrate Interaction

Senbin Chen; Zeke Li; Yanggui Wu; Nasir Mahmood; Frédéric Lortie; Julien Bernard; Wolfgang H Binder; Jintao Zhu

doi:10.1002/anie.202203876

Hydrogen-Bonded Supramolecular Polymer Adhesives: Straightforward Synthesis and Strong Substrate Interaction

Angew Chem Int Ed Engl. 2022 Jul 4;61(27):e202203876. doi: 10.1002/anie.202203876. Epub 2022 May 3.

Authors

Senbin Chen¹, Zeke Li¹, Yanggui Wu¹, Nasir Mahmood², Frédéric Lortie³, Julien Bernard³, Wolfgang H Binder⁴, Jintao Zhu¹

Affiliations

¹ Key Laboratory of Materials Chemistry for Energy Conversion and Storage, Ministry of Education (HUST), School of Chemistry and Chemical Engineering, Huazhong University of Science and Technology (HUST), Wuhan, 430074, China.
² Institute of Chemistry, Chair of Macromolecular Chemistry, Faculty of Natural Sciences II, Martin-Luther University Halle-Wittenberg, Kurth-Mothes-Strasse 2, 06120, Halle (Saale), Germany.
³ Université de Lyon, CNRS, UMR 5223, Ingénierie des Matériaux Polymères, Université Lyon 1, INSA Lyon, UJM, 69621, Villeurbanne cedex, France.
⁴ Institute of Chemistry, Martin-Luther University Halle-Wittenberg, von Danckelmann-Platz 4, 06120 Halle, Saale), Germany.

PMID: 35426214
DOI: 10.1002/anie.202203876

Abstract

High-performance adhesives are of great interest in view of industrial demand. We herein identify a straightforward synthetic strategy towards universal hydrogen-bonded (H-bonded) polymeric adhesives, using a side-chain barbiturate (Ba) and Hamilton wedge (HW) functionalized copolymer. Starting from a rubbery copolymer containing thiolactone derivatives, Ba and HW moieties are tethered as pendant groups via an efficient one-pot two-step amine-thiol-bromo conjugation. Hetero-complementary Ba/HW interactions thus yield H-bonded supramolecular polymeric networks. In addition to an enhanced polymeric network integrity induced by specific Ba/HW association, the presence of individual Ba or HW moieties enables strong binding to a range of substrates, outstanding compared to commercial glues and reported adhesives.

Keywords: Amine-Thiol-Bromo Conjugation; Hydrogen Bonds; Self-Assembly; Supramolecular Polymeric Adhesives.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Adhesives*
Chemical Phenomena
Hydrogen
Hydrogen Bonding
Polymers* / chemistry

Substances

Adhesives
Polymers
Hydrogen