Ring opening metathesis polymerization (ROMP) was carried out on Diels-Alder adducts formed from reactions between chalcones and cyclopentadiene. Most of the chalcones gave predominantly endo-adducts and the exo-adducts were obtained in good yields from reacting cyclopentadiene with furfurylidine acetone and N,N,diethylaminobenzylidine-(4-hydroxy)acetophenone. These exo-adducts were subjected to ROMP using Grubbs catalyst, bis(tricyclohexylphosphine)benzylidinedichloride. The monomers and polymers were characterized using spectroscopic techniques like FT-IR, (HNMR)-H-1. The polymers were characterized using TGA, DSC, and GPC. The polymers were found to possess fluorescent properties and poly[2-(4-diethylamino)phenyl-3,5-divinylcyclopentyl](4-hydroxyphenyl) methanone was found to have good emissive property at two wavelengths. (c) 2008 Wiley Periodicals, Inc.