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Mechanistic Investigations on a Diynone Type Photoinitiator
Author(s) -
Seidl Bernhard,
Liska Robert
Publication year - 2007
Publication title -
macromolecular chemistry and physics
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.57
H-Index - 112
eISSN - 1521-3935
pISSN - 1022-1352
DOI - 10.1002/macp.200600432
Subject(s) - photoinitiator , benzophenone , chemistry , monomer , hydrogen atom abstraction , photochemistry , acetonitrile , polymer chemistry , isopropyl , cycloaddition , polymerization , isopropyl alcohol , hydrogen , organic chemistry , polymer , catalysis
Recently, it has been shown that 1,5‐diphenyl‐penta‐1,4‐diyn‐3‐one (DPD) has some surprising characteristics as photoinitiator for free radical polymerization. In the present investigations we focused on the photochemistry in hydrogen donating isopropyl alcohol (IPA) and neutral acetonitrile (MeCN). HPLC and column chromatographic separation were applied for photoproduct identification. Different types of radical quenchers such as the stable radical TEMPO and the non‐polymerizable monomer methyl t ‐butacrylate ( t ‐BAM) were also used to identify the initiating species. In IPA, fast hydrogen abstraction reaction similar to that of benzophenone was found, whereas the hydrogen donor is the initiating molecule. Significantly, slower 2 + 2 cycloaddition reaction involving the carbonyl group is the predominant pathway in MeCN. Experiments with t ‐BAM indicated that DPD is directly responsible for the initiation process.

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