Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 61, Issue 15, Pages -Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202113076
Keywords
Hydrogels; Photoacid Generator; Photocycloaddition; Visible Light; Wavelength-Orthogonal
Categories
Funding
- Australian Research Council (ARC) [FL170100014]
- Queensland University of Technology (QUT)
- Volkswagen Foundation
- ARC Discovery grant targeted at red-shifting photoligation chemistry
- Karlsruhe Institute of Technology (KIT)
- Australian Research Council [FL170100014] Funding Source: Australian Research Council
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In this study, we present a wavelength-orthogonal crosslinking method for hydrogel networks using two red-shifted chromophores. The photoreactivity of one chromophore is pH-dependent, and by incorporating a suitable photoacid generator, the activation wavelength of the other chromophore can be selectively controlled. This system was successfully applied to the design of hydrogels with independently tunable stiffness using green or blue light.
Herein, we introduce the wavelength-orthogonal crosslinking of hydrogel networks using two red-shifted chromophores, i.e. acrylpyerene (AP, lambda(activation)=410-490 nm) and styrylpyrido[2,3-b]pyrazine (SPP, lambda(activation)=400-550 nm), able to undergo [2+2] photocycloaddition in the visible-light regime. The photoreactivity of the SPP moiety is pH-dependent, whereby an acidic environment inhibits the cycloaddition. By employing a spiropyran-based photoacid generator with suitable absorption wavelength, we are able to restrict the activation wavelength of the SPP moiety to the green light region (lambda(activation)=520-550 nm), enabling wavelength-orthogonal activation of the AP group. Our wavelength-orthogonal photochemical system was successfully applied in the design of hydrogels whose stiffness can be tuned independently by either green or blue light.
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