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Development of dipyridine‐based coordinative polymers for reusable heterogeneous catalysts
Author(s) -
Chang HsiangChun,
Li JiaQi,
Lin ChingKai,
Hsu YuJung,
Tu TsungHan,
Hsieh YiLiang,
Hsu HsiuHao,
Lee GeneHsiang,
Liu YiHung,
Peng ChiHow
Publication year - 2019
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.201900191
Subject(s) - chemistry , catalysis , monomer , copolymer , polymer chemistry , pyridine , reactivity (psychology) , methyl acrylate , alkylation , hydrolysis , acrylate , isopropyl , polymerization , acrylamide , metal ions in aqueous solution , polymer , metal , organic chemistry , medicine , alternative medicine , pathology
Poly(di(pyridin‐2‐yl)methyl acrylate) (PDPyMA), which was obtained by the free radical polymerization of designed coordinative monomer of di(pyridin‐2‐yl)methyl acrylate, is able to coordinate with various metal ions to form heterogeneous catalysts for diverse catalytic reactions. The Pd and Cu complexes supported by PDPyMA were developed for the heterogeneous Suzuki‐Miyaura reaction and Friedel‐Crafts alkylation, respectively. The PDPyMA‐based catalysts showed no significant decline of reactivity after five times recycling. However, the hydrolysis of the PDPyMA backbone under alkaline conditions limited the catalytic efficiency of this heterogeneous catalyst so that the coordinative monomer was redesigned as 1,1‐di(pyridine‐2‐yl)‐2‐(4‐vinylphenyl)ethan‐1‐ol and then 2,2′‐(1‐methoxy‐2‐(4‐vinylphenyl)ethane‐1,1‐diyl)dipyridine (MVPhDPy). With copolymerization of N ‐isopropyl acrylamide (NIPAM), the efficiency of polymer‐based heterogeneous catalysts could be further raised, demonstrated by the increased turn over number in the Suzuki‐Miyaura reaction, which approached 5,260 by using the catalyst formed from poly(MVPhDPy‐ co ‐NIPAM) and Pd(OAc) 2 . poly(MVPhDPy‐ co ‐NIPAM) copolymer, therefore, could be a versatile platform to support different metal ions for various heterogeneous catalytic reactions.