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Highly Reactive Thiol‐Norbornene Photo‐Click Hydrogels: Toward Improved Processability
Author(s) -
Hoorick Jasper,
Gruber Peter,
Markovic Marica,
Rollot Mélanie,
Graulus GeertJan,
Vagenende Maxime,
Tromayer Maximilian,
Erps Jürgen,
Thienpont Hugo,
Martins José C.,
Baudis Stefan,
Ovsianikov Aleksandr,
Dubruel Peter,
Vlierberghe Sandra
Publication year - 2018
Publication title -
macromolecular rapid communications
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.348
H-Index - 154
eISSN - 1521-3927
pISSN - 1022-1336
DOI - 10.1002/marc.201800181
Subject(s) - methacrylamide , norbornene , gelatin , self healing hydrogels , materials science , click chemistry , surface modification , polymer chemistry , biocompatibility , polymerization , photoinitiator , chemical engineering , copolymer , chemistry , organic chemistry , polymer , monomer , composite material , acrylamide , engineering , metallurgy
In the present work, gelatin type B is modified with highly reactive norbornene functionalities (Gel‐NB) following a one‐pot synthesis approach to enable subsequent thiol–ene photo‐click crosslinking. The modification strategy displays close control over the amount of introduced functionalities. Additionally, Gel‐NB exhibits considerably improved processing capabilities in terms of two‐photon polymerization when benchmarked to earlier‐reported crosslinkable gelatin derivatives (e.g., gelatin‐methacrylamide (Gel‐MOD) and gelatin‐methacrylamide‐aminoethylmethacrylate (Gel‐MOD‐AEMA)). The improvement is especially apparent in terms of minimally required laser power (20 mW vs ≥60 mW (Gel‐MOD) vs ≥40 mW (Gel‐MOD‐AEMA) at 100 mm s −1 scan speed) and processable concentration range (≥5 w/v% vs ≥10 w/v% (Gel‐MOD/Gel‐MOD‐AEMA)). Furthermore, the proposed functionalization scheme maintains the excellent biocompatibility and cell interactivity of gelatin. Additionally, the norbornene functionalities have potential for straightforward postprocessing “thiol–ene” surface grafting of active molecules. As a consequence, a very promising material toward tissue engineering applications and more specifically, biofabrication, is presented.