Glassy Fluorene and Sulfone Polyesters with High Refractive Index and Thermal Stability Whose Monomers Induce Estrogenic Bioactivity.

Two new diacid monomers containing either fluorene or sulfone moieties polymerize via step-growth polymerization in the presence of their diol counterparts or alkyl diols (ethylene glycol and 1,6-hexanediol), forming eight new structure polyesters. The polymers exhibit high optical transparency in the thin-film form with refractive indices ranging from 1.56 to 1.69, tunable glass transition temperatures from ca. 40 to 116 °C with no melting temperature, and resistance to thermal degradation in a nitrogenous atmosphere, reaching 350-398 °C before observing 10% weight loss. Their molecular weights, M , range from ca. 17 to 77 kDa, with an average polydispersity, , of 1.5, and average purified yields of 82%. The polymers absorb light primarily in the UV region from ca. 228 to 320 nm with no absorption from 320 to 800 nm. A critical finding is that some of the fluorene and sulfone monomers induce negative bioactivity and even cell death in T47D-KBLuc cells, a breast cancer cell line, at high concentrations. This report details the project inspiration, monomer synthesis, polymerization steps, structural confirmation, material characterization, and the impact of the new monomer's estrogenic and antiestrogenic bioactivity.