Preparation, characterization, and properties of fluorene-containing benzoxazine and its corresponding cross-linked polymer

Abstract

A benzoxazine compound (FDP-FBz), which possesses a fluorene group and two terminal furan groups, and its corresponding cross-linked polymer (CR-FDP-FBz) have been prepared using 4,4'-(9-fluorenylidene)diphenol (FDP), furfurylamine, and formaldehyde as precursors. The chemical structure of FDP-FBz has been characterized with Fouriertransform infrared and 1H nuclear magnetic resonance spectroscopies. FDP-FBz displays a melting point at about 173 °C and a processing window of 52 °C as well as good solubility in common organic solvents. As a result, FDP-FBz can be fabricated in both molten and solution processes. Under an excitation at 365 nm, FDP-FBz exhibits a photoluminescent (PL) emission at about 445 nm. The PL intensity of FDP-FBz is as high as sixfolds of the intensity recorded with FDP. CRFDP-FBz displays a glass transition temperature of 215 °C, a high storage modulus of 3.1 GPa, a 10% weight loss at 384 °C, and a high char yield of 56 wt % (900 °C, in nitrogen). Moreover, CR-FDP-FBz has a high refractive index of about 1.65 as a result of incorporating fluorene groups to its structure. © 2010 Wiley Periodicals, Inc.