Mild and modular surface modification of cellulose via Hetero Diels-Alder (HDA) cycloaddition

Goldmann, Anja S., Tischer, Thomas, Barner, Leonie, Bruns, Michael, & Barner-Kowollik, Christopher (2011) Mild and modular surface modification of cellulose via Hetero Diels-Alder (HDA) cycloaddition. Biomacromolecules, 12(4), pp. 1137-1145.

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A combination of reversible addition-fragmentation chain transfer (RAFT) polymerization and hetero Diels-Alder (HDA) cycloaddition was used to effect, under mild (T approximate to 20 degrees C), fast, and modular conditions, the grafting of poly(isobornyl acrylate) (M-n = 9800 g mol(-1), PDI = 1.19) onto a solid cellulose substrate. The active hydroxyl groups expressed on the cellulose fibers were converted to tosylate leaving groups, which were subsequently substituted by a highly reactive cyclopentadienyl functionality (Cp). By employing the reactive Cp-functionality as a diene, thiocarbonyl thio-capped poly(isobornyl acrylate) synthesized via RAFT polymerization (mediated by benzyl pyridine-2-yldithioformiate (BPDF)) was attached to the surface under ambient conditions by an HDA cycloaddition (reaction time: 15 h). The surface-modified cellulose samples were analyzed in-depth by X-ray photoelectron spectroscopy, scanning electron microscopy, elemental analysis, Fourier transform infrared (FT-IR) spectroscopy as well as Fourier transform infrared microscopy employing a focal plane array detector for imaging purposes. The analytical results provide strong evidence that the reaction of suitable dienophiles with Cp-functional cellulose proceeds under mild reaction conditions (T approximate to 20 degrees C) in an efficient fashion. In particular, the visualization of individual modified cellulose fibers via high-resolution FT-IR microscopy corroborates the homogeneous distribution of the polymer film on the cellulose fibers.

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ID Code: 97484
Item Type: Journal Article
Refereed: Yes
DOI: 10.1021/bm101461h
ISSN: 1525-7797
Divisions: Current > QUT Faculties and Divisions > Chancellery
Current > Schools > School of Chemistry, Physics & Mechanical Engineering
Current > Institutes > Institute for Future Environments
Current > QUT Faculties and Divisions > Science & Engineering Faculty
Deposited On: 28 Jul 2016 02:46
Last Modified: 03 Aug 2016 04:51

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