The synthesis and free radical polymerization of a methacrylamide monomer, 5, bearing non-covalently attached cyclodextrins and the chalcone function with a barrier group, is described. The first step of preparation of the monomer was the condensation of 4-( N -methacryloyl-6-aminohexanoylamino)- acetophenone, 1 , with 4-nitrobenzaldehyde. The resulting 1-( N -methacryloyl-6- aminohexanoyl-4-aminophenyl)-3-(4-nitrophenyl)-2-propen-1-one, 2 , was reduced with tin(II) chloride dihydrate to the corresponding 1-( N -methacryloyl-6-aminohexanoyl- 4-aminophenyl)-3-(4-aminophenyl)-2-propen-1-one, 3 . After this, the aminochalcone was condensed with a barrier group, triphenylacetyl chloride, yielding 1-( N -methacryloyl-6-aminohexanoyl-4-aminophenyl)-3-( N’ -triphenylacetyl- 4-aminophenyl)-2-propen-1-one, 4 . Monomer 4 was copolymerized with methyl methacrylate to the model polymer poly[ 4 -co- methyl methacrylate], 6 , and also complexed with dimethylated β - cyclodextrin to the semi-rotaxane ( 4 / 2,6-Me2-β - CD) 5 , which was copolymerized with methyl methacrylate, yielding a polyrotaxane ( 5 - co- methyl methacrylate) 7 , containing a cyclodextrin ring in the side-chain. The semi-rotaxane 5 and both copolymers 6 and 7 were characterized spectroscopically and also by means of differential scanning calorimetry, gel permeation chromatography and thermogravimetrical analysis, and - in the case of 5 - by mass spectrometry. Furthermore, the UV-induced E/Z -isomerization of both polymers 6 and 7 was examined in tetrahydrofuran solution. A retarding effect of the noncovalently attached cyclodextrin was finally detected.