Inverse electron demand Diels–Alder (iEDDA) functionalisation of macroporous poly(dicyclopentadiene) foams

Abstract

Inverse electron demand Diels-Alder reactions performed on the double bonds in open cellular macroporous poly(dicyclopentadiene) monoliths yield a high degree of functionalisation (up to 2 mmol pyridazines per g or 8 mmol N per g) with grafted di(pyridyl)pyridazines in a single step.

Dye-functionalized polymers via ring opening metathesis polymerization: principal routes and applications

“…In another novel approach, tetrazines were used to graft dipyridylpyridazine ligands in an inverse electron demand Diels-Alder reaction to a polydicyclopentadiene foam prepared by emulsion templating. Successful grafting of the ligands was proven by the formation of red phosphorescent europium complexes on the surface of the polymeric foams [91].…”

Inverse‐Electron‐Demand Diels–Alder Reactions: Principles and Applications

“…Slugovca nd coworkers report that the iEDDA reaction enables postfunctionalization of these materials in as ingle step. [116] Tetrazine 93 is added to the poly(dicyclopentadiene), and the mixturei s heated for 2days. Subsequent elementala nalysis shows that every fourth doubleb ond is functionalized.…”

Kinetic studies of inverse electron demand Diels–Alder reactions (iEDDA) of norbornenes and 3,6-dipyridin-2-yl-1,2,4,5-tetrazine

“…Molecules bearing two or more tetrazine residues have been applied for crosslinking leading to single-chain polymer nanoparticles 12 or hydrogels 13,14 . Furthermore, tetrazines have been used to modify MOFs (metal-organic frameworks), 15 fullerenes (which then were used as modifier layers in solar cells), 16 carbon nanotubes 17,18 and macroporous polymer foams 19 . Due to their straightforward synthetic availability, norbornenes have been more abundantly used in materials science than trans -cyclooctenes (which are also known to readily isomerize into the unreactive cis -form).…”