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Functionalization of cis‐1,4‐polyisoprene using hypervalent iodine compounds with tetrazole ligands
Author(s) -
Kumar Rajesh,
Sayala Kapil Dev,
Cao Yakun,
Tsarevsky Nicolay V.
Publication year - 2020
Publication title -
journal of polymer science
Language(s) - English
Resource type - Journals
eISSN - 2642-4169
pISSN - 2642-4150
DOI - 10.1002/pola.29500
Subject(s) - chemistry , polymer chemistry , hypervalent molecule , tetrazole , methyl iodide , iodide , methyl methacrylate , azide , iodine , nucleophilic substitution , polymerization , polymer , organic chemistry
Hypervalent iodine(III) compounds with tetrazole ligands C 6 H 5 I(N 4 CR) 2 (R CH 3 , C 6 H 5 , 4‐CH 3 C 6 H 4 ) reacted, in the presence of elemental iodine, with the double bonds in cis‐1,4‐polyisoprene (polyIP) to afford iodo‐tetrazolylated polymers. The alkyl‐iodide groups in the products of the polyIP functionalization were utilized as macro chain‐transfer agents for the iodine‐transfer polymerization of methyl methacrylate, which yielded brush polymers with well‐defined poly(methyl methacrylate) side chains. In addition, the iodo‐tetrazolylated polymers were reacted with NaN 3 in DMF at room temperature, and it was noticed that, in addition to nucleophilic substitution, elimination reactions took place. However, the presence of azide groups was taken advantage of and successful click chemistry‐type of grafting‐onto reactions were carried out with alkyne‐capped poly(ethylene oxide) in the presence of CuBr and N , N , N′ , N″ , N″ ‐pentamethyldiethylenetriamine. The thermal decomposition of both the iodo‐tetrazolylated and the azido‐tetrazolylated polymers was exothermic, especially for the latter materials. © 2019 Wiley Periodicals, Inc. J. Polym. Sci. 2020 , 58 , 172–180