Multicyclic Polyesters by Polycondensation of 5,5‘,6,6‘-Tetrahydroxy-3,3,3‘,3‘-tetramethylspirobisindane with Dicarboxylic Acid Dichlorides

Abstract

5,5‘,6,6‘-Tetrahydroxy-3,3,3‘,3‘-tetramethylspirobisindane (TTSBI) was polycondensed with 2 equiv of sebacoyl chloride or 1,6-hexanediol bischloroformiate. Although the monomer concentration was varied by a factor of 10, partially or totally cross-linked polyesters were obtained in all experiments. Analogous polycondensations of TTSBI were conducted with double molar amounts of α,ω-bis(4-chlorocarbonylphenoxy)alkanes or α,ω-bis(3-chlorocarbonylphenoxy)alkanes. Depending on concentration and structure of the dicarboxylic acid dichlorides, either gels or soluble multicyclic polyesters were obtained and characterized by 1H and 13C NMR spectroscopy, MALDI-TOF, and FAB mass spectrometry. SEC measurements revealed broad molecular weight distributions, and DSC measurements indicated an amorphous character of all multicycles.