MACROCYCLIC POLYMERS .1. SYNTHESIS OF A POLY(ESTER CROWN) BASED ON BIS(5-CARBOXY-1,3-PHENYLENE)-32-CROWN-10 AND 4,4'-ISOPROPYLIDENEDIPHENOL (BISPHENOL-A)

A semirigid 32-membered ring diester crown ether, bis(5-carbomethoxy-1,3-phenylene)-32-crown-10 (3), has been synthesized in one step using methyl 3,5-dihydroxybenzoate (1) and tetra(ethylene glycol) dichloride (2) in the presence of sodium hydride in N,N-dimethylformamide (DMF). This diester crown has been converted to the diacid crown 5. A direct polycondensation reaction of bis(5-carboxy-1,3-phenylene)-32-crown-10 (5) and 4,4'-isopropylidenediphenol (Bisphenol A) (6) using tosyl chloride in pyridine in the presence of DMF formed a high molecular weight poly(ester crown) (7). The polymer is soluble in common organic solvents such as chloroform and THF. It has a glass transition temperature (T(g)) of 65 degrees-C; also it shows quite high thermal stability, 5% weight loss by TGA at 355-degrees-C in air.