Abstract
In this paper we explore RAFT (reversible addition-fragmentation chain transfer) single unit monomer insertion (SUMI) into dithiobenzoates. Styrene and N-isopropylacrylamide (NIPAm) were successfully inserted into 2-cyanopropan-2-yl dithiobenzoate. Attempted SUMI of methyl methacylate (MMA) provided an oligomeric insertion product due to the low transfer constant of the dithiobenzoate in MMA polymerization. A very low yield with maleic anhydride (MAH) reflects the low reactivity of MAH towards 2-cyanopropan-2-yl radicals. We also examined insertion of MAH, styrene and NIPAm into the styrene SUMI product. Insertion of MAH was rapid and efficient. SUMI with styrene and NIPAm was slower, which is attributed both to the low monomer concentrations used and the poor leaving group ability of the propagating species. The reaction with NIPAm is additionally complicated by initiator-derived by-products.
Original language | English |
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Title of host publication | Sequence-Controlled Polymers |
Subtitle of host publication | Synthesis, Self-Assembly, and Properties |
Editors | Jean-François Lutz, Tara Y. Meyer, Makoto Ouchi, Mitsuo Sawamoto |
Place of Publication | Washington DC |
Publisher | American Chemical Society |
Chapter | 9 |
Pages | 133-147 |
Number of pages | 15 |
Volume | 1170 |
ISBN (Electronic) | 9780841230019 |
DOIs | |
Publication status | Published - 2014 |
Externally published | Yes |
Event | International Symposium on Sequence-controlled Polymers: Synthesis, Self-Assembly, and Properties / American-Chemical-Society National Meeting 2013 - Indianapolis, United States of America Duration: 8 Sept 2013 → 12 Sept 2013 Conference number: 1st |
Publication series
Name | ACS Symposium Series |
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Volume | 1170 |
ISSN (Print) | 00976156 |
ISSN (Electronic) | 19475918 |
Conference
Conference | International Symposium on Sequence-controlled Polymers: Synthesis, Self-Assembly, and Properties / American-Chemical-Society National Meeting 2013 |
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Country/Territory | United States of America |
City | Indianapolis |
Period | 8/09/13 → 12/09/13 |
Other | The first international symposium on sequence-controlled polymers was organized at the 246th American Chemical Society national meeting in Indianapolis. All the chapters in this volume are related to the invited oral presentations that were given during the symposium |