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 Fourier-transform infrared and H-1, nuclear magnetic resonance spectroscopies. FDP-FBz displays a melting point at about 173 degrees C and a processing window of 52 degrees 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 CR-FDP-FBz displays a glass transition temperature of 215 C, a high storage modulus of 3 1 GPa, a 10% weight loss at 384 degrees C, and a high char yield of 56 wt % (900 degrees 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 (C) 2010 Wiley Periodicals, Inc J Polym Sci Part A Polym Chem 48. 4020-4026, 2010