Elastomeric polyamide biomaterials with stereochemically tuneable mechanical properties and shape memory

TY - JOUR

T1 - Elastomeric polyamide biomaterials with stereochemically tuneable mechanical properties and shape memory

AU - Worch, Joshua C

AU - Weems, Andrew C

AU - Yu, Jiayi

AU - Arno, Maria C

AU - Wilks, Thomas R

AU - Huckstepp, Robert T R

AU - O'Reilly, Rachel K

AU - Becker, Matthew L

AU - Dove, Andrew P

PY - 2020/6/26

Y1 - 2020/6/26

N2 - Biocompatible polymers are widely used in tissue engineering and biomedical device applications. However, few biomaterials are suitable for use as long-term implants and these examples usually possess limited property scope, can be difficult to process, and are non-responsive to external stimuli. Here, we report a class of easily processable polyamides with stereocontrolled mechanical properties and high-fidelity shape memory behaviour. We synthesise these materials using the efficient nucleophilic thiol-yne reaction between a dipropiolamide and dithiol to yield an α,β - unsaturated carbonyl moiety along the polymer backbone. By rationally exploiting reaction conditions, the alkene stereochemistry is modulated between 35-82% cis content and the stereochemistry dictates the bulk material properties such as tensile strength, modulus, and glass transition. Further access to materials possessing a broader range of thermal and mechanical properties is accomplished by polymerising a variety of commercially available dithiols with the dipropiolamide monomer.

AB - Biocompatible polymers are widely used in tissue engineering and biomedical device applications. However, few biomaterials are suitable for use as long-term implants and these examples usually possess limited property scope, can be difficult to process, and are non-responsive to external stimuli. Here, we report a class of easily processable polyamides with stereocontrolled mechanical properties and high-fidelity shape memory behaviour. We synthesise these materials using the efficient nucleophilic thiol-yne reaction between a dipropiolamide and dithiol to yield an α,β - unsaturated carbonyl moiety along the polymer backbone. By rationally exploiting reaction conditions, the alkene stereochemistry is modulated between 35-82% cis content and the stereochemistry dictates the bulk material properties such as tensile strength, modulus, and glass transition. Further access to materials possessing a broader range of thermal and mechanical properties is accomplished by polymerising a variety of commercially available dithiols with the dipropiolamide monomer.

UR - http://www.scopus.com/inward/record.url?scp=85086859616&partnerID=8YFLogxK

U2 - 10.1038/s41467-020-16945-8

DO - 10.1038/s41467-020-16945-8

M3 - Article

C2 - 32591525

VL - 11

JO - Nature Communications

JF - Nature Communications

SN - 2041-1723

IS - 1

M1 - 3250

ER -