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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 20, Number 5
BKCSDE 20(5)
May 20, 1999 

Syntheses and Potentiometric Properties of Polyethers Containing Thiazole and Oxazole Derivatives
Jun-Hyeak Choi, Young Kook Koh, II-Chun Kwon, Hong-Seok Kim, Hyun Joo Park, Sang Jin Kim, Geun Sig Cha, Hakhyun Nam
A series of polyethers containing the thiazole or oxazole subcyclic moiety have been synthesized. Reaction of 2-aryl-4-hydroxymethylthiazole with tetra- and pentaethylene glycol di-p-tosylate in THF provided corresponding α,ω-bis[2'-aryl-4'-methylthiazole]polyethylene glycol in good yields. Similar treatment of 2-phenyl-4-hydroxymethyloxazole 7 and 2-phenyl-5-hydroxymethyloxazole 8 with tetraethylene glycol di-p-tosylate yielded the corresponding 1,13-bis [2'-phenyl-4'-methyloxazole]tetraethylene glycol 16 and 1,13-bis[2'-phenyl-5'-methyloxazole]tetraethylene glycol 17 in 69 and 43% yields in respectively. The potentiometric properties of PVC-based ion selective membranes containing 66 wt% o-nitrophenyloctyl ether (NPOE) and 4 wt% polyethers 9-17 have been examined. The membranes containing thiazole and oxazole polyether derivatives exhibited high selectivity toward silver (I) ion. It was observed that the response slopes of the electrodes to silver ion vary with the length of polyether chain linking two thiazole subcyclic moiety. Potentiometric data suggest that the number of ether units, CH2OCH2, for phenylthiazole derivatives be greater than 5 to result in near-Nernstian response. However, the response behaviors of the membrane electrodes based on phenyloxazole podands 16 and 17, which have different orientation, were correspondingly similar to those of the electrodes based on phenylthiazole podands 9 and 10. On the other hand, the ISEs based on thiazole polyether derivatives with different terminal substituents, e.g., phenyl 10, naphtyl 14, and thienyl 15, except that with pyridyl 12, exhibited little difference in their potentiometric properties.
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