TY - JOUR
T1 - Highly Norbornylated Cellulose and Its “Click” Modification by an Inverse-Electron Demand Diels–Alder (iEDDA) Reaction
AU - Wappl, Christina
AU - Schallert, Viktor
AU - Slugovc, Christian
AU - Knall, Astrid-Caroline
AU - Spirk, Stefan
N1 - Publisher Copyright:
© 2021 by the authors. Licensee MDPI, Basel, Switzerland.
PY - 2021/3/4
Y1 - 2021/3/4
N2 - A facile, catalyst-free synthesis of a norbornylated cellulosic material (NC) with a high degree of substitution (2.9) is presented by direct reaction of trimethylsilyl cellulose with norbornene acid chloride. The resulting NC is highly soluble in organic solvents and its reactive double bonds were exploited for the copper-free inverse-electron demand Diels–Alder (iEDDA) “click” reaction with 3,6-di(pyridin-2-yl)-1,2,4,5-tetrazine. Reaction kinetics are comparable to the well-known Huisgen type 1,3-dipolar cycloaddition of azide with alkynes, while avoiding toxic catalysts
AB - A facile, catalyst-free synthesis of a norbornylated cellulosic material (NC) with a high degree of substitution (2.9) is presented by direct reaction of trimethylsilyl cellulose with norbornene acid chloride. The resulting NC is highly soluble in organic solvents and its reactive double bonds were exploited for the copper-free inverse-electron demand Diels–Alder (iEDDA) “click” reaction with 3,6-di(pyridin-2-yl)-1,2,4,5-tetrazine. Reaction kinetics are comparable to the well-known Huisgen type 1,3-dipolar cycloaddition of azide with alkynes, while avoiding toxic catalysts
KW - Cellulose
KW - Cellulose ester
KW - Click chemistry
KW - Copper-free
KW - Norbornene cellulose
KW - iEDDA
UR - https://doi.org/10.3390/molecules26051358
UR - http://www.scopus.com/inward/record.url?scp=85103862478&partnerID=8YFLogxK
U2 - 10.3390/molecules26051358
DO - 10.3390/molecules26051358
M3 - Article
SN - 1420-3049
VL - 26
JO - Molecules
JF - Molecules
IS - 5
M1 - 1358
ER -