Synthesis, characterization, and complexing properties of a polymethacrylate bearing pendant macroheterocyclic structures

Autor: J. E. Herweh
Rok vydání: 1985
Předmět:
Zdroj: Journal of Polymer Science: Polymer Chemistry Edition. 23:2767-2778
ISSN: 1542-9369
0360-6376
DOI: 10.1002/pol.1985.170231105
Popis: The synthesis of a polymerizable methacrylate bearing the dibenzo-18-crown-6 moiety (5) was effected in three steps by condensation of 3,4-dihydroxybenzaldehyde with 1,2-bis[2′-(2″-chloroethoxy)ethoxy]benzene (2), reduction of the resulting 4-formyldibenzo-18-crown-6 (3) to 4 and subsequent reaction of 4 with methacryloyl chloride. The methacrylate (5) was polymerized in solution using 2,2′-azobis(isobutyronitrile) (AIBN) as the initiator and gave a solid polymer (6) having a midrange Tg of 67°C. The polymethacrylate bearing pendant crown-ether structure (6) was found to effectively complex potassium ions and was clearly more effective in its complexing ability than dibenzo-18-crown-6 (7) or a polyurethane bearing the dibenzo-18-crown-6 moiety (8) in the polymer backbone. The subject polymer (6) was also found to complex and consequently solubilize several metal 7,7,8,8-tetracyanoquinodimethane (TCNQ) salts to give semiconducting compositions. Evidence is given that in the presence of the neutral acceptor molecule, 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ), the polymethacrylate (6) acting as a donor, gives rise to a charge-transfer (C/T) complex.
Databáze: OpenAIRE
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