Ambient temperature ligation of diene functional polymer and peptide strands onto cellulose via photochemical and thermal protocols

Tischer, T., Claus, T. K., Oehlenschlaeger, K. K., Trouillet, V., Bruns, M., Welle, A., Linkert, K., Goldmann, A. S., Börner, H. G., & Barner-Kowollik, C. (2014) Ambient temperature ligation of diene functional polymer and peptide strands onto cellulose via photochemical and thermal protocols. Macromolecular Rapid Communications, 35(12).

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Abstract

In the present contribution, two novel ambient temperature avenues are introduced to functionalize solid cellulose substrates in a modular fashion with synthetic polymer strands (poly(trifluoro ethyl methacrylate), PTFEMA, M n = 4400 g mol-1, D = 1.18) and an Arg-Gly-Asp (RGD) containing peptide sequence. Both protocols rely on a hetero Diels-Alder reaction between an activated thiocarbonyl functionality and a diene species. In the first - thermally activated - protocol, the cellulose features surface-expressed thiocarbonylthio compounds, which readily react with diene terminal macromolecules at ambient temperature. In the second protocol, the reactive ene species are photochemically generated based on a phenacyl sulfide-decorated cellulose surface, which upon irradiation expresses highly reactive thioaldehyde species. The generated functional hybrid surfaces are characterized in-depth via ToF-SIMS and XPS analysis, revealing the successful covalent attachment of the grafted materials, including the spatially resolved patterning of both synthetic polymers and peptide strands using the photochemical protocol. The study thus provides a versatile platform technology for solid cellulose substrate modification via efficient thermal and photochemical ligation strategies. © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

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11 citations in Web of Science®

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ID Code: 99411
Item Type: Journal Article
Refereed: Yes
Additional Information: Cited By :9
Export Date: 5 September 2016
CODEN: MRCOE
Correspondence Address: Barner-Kowollik, C.; Preparative Macromolecular Chemistry, Institut für Technische Chemie und Polymerchemie, Karlsruhe Institute of Technology (KIT), Engesserstr. 18, 76128 Karlsruhe, Germany; email: christopher.barner-kowollik@kit.edu
Chemicals/CAS: cellulose, 61991-22-8, 68073-05-2, 9004-34-6; poly(methyl methacrylate), 39320-98-4, 9008-29-1; Alkadienes; arginyl-glycyl-aspartic acid; Cellulose; Oligopeptides; poly(2,2,2-trifluoroethylmethacrylate); Polymethyl Methacrylate
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Keywords: cellulose, grafting-to, peptides, photoconjugation, surface modification, Grafting (chemical), Hybrid materials, Olefins, Secondary ion mass spectrometry, Substrates, Surface treatment, Temperature, Cellulose substrates, Covalent attachment, Ethyl methacrylates, Hetero Diels-Alder reaction, Platform technology, Thermally activated, alkadiene, arginyl-glycyl-aspartic acid, oligopeptide, poly(2,2,2-trifluoroethylmethacrylate), poly(methyl methacrylate), chemical structure, chemistry, photochemistry, synthesis, Alkadienes, Molecular Structure, Oligopeptides, Photochemical Processes, Polymethyl Methacrylate
DOI: 10.1002/marc.201400088
ISSN: 10221336
Divisions: Current > Schools > School of Chemistry, Physics & Mechanical Engineering
Current > Institutes > Institute for Future Environments
Current > QUT Faculties and Divisions > Science & Engineering Faculty
Deposited On: 22 Sep 2016 04:50
Last Modified: 28 Sep 2016 03:29

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