The radical copolymerization of 9-anthrylmethyl methacrylate (1) with N-phenylmaleimide (2), initiated by 2,2 '-azoisobutyronitrile at 60 "C in 1 ,Cdioxane, was investigated. Simultaneously with the copolymerization a Diels-Alder cycloaddition of 2 to the anthracene nucleus takes place as side reaction. A charge transfer complex formation between the two monomers was evidenced by 'H NMR spectroscopy. The stability constant of the complex, which is an intermediate in the cycloaddition reaction, was found to be 0,05 1 . mol-' . C. I. Simionescu, M. Grigoras, G. OnofreiThe present paper deals with the radical copolymerization of the electron donor/ electron acceptor monomer pair 9-anthrylmethyl methacrylate (l)/N-phenylmaleimide (2), which can form a Diels-Alder cycloadduct (3). Experimental partMaterials: 9-Anthrylmethyl methacrylate (1) was obtained from the reaction of methacryloyl chloride with 9-anthranylmethanol'). N-Phenylmaleimide (2) was synthesized from maleic anhydride and aniline in a two stage reaction, according to the original method developed by Searle6). The monomers were recrystallized twice from methanol.The Diels-Alder cycloadduct (3) was synthesized by heating the two compounds (1,4dioxane solution, 0,5 mol/l total concentration) in a 1 : 1 mole ratio at 60°C for 24 h. After solvent evaporation, the adduct was recrystallized from methanol. The yield was quantitative.Copolymerization: Copolymerization reactions were carried out at 60 "C in sealed ampoules using 1,rl-dioxane as solvent. The total concentration of monomers was 0,5 mol/l in all cases, and the copolymer composition was varied by the ratio of the two monomers. 2,2'-Azoisobutyronitrile (AIBN) was used as initiator (1 mol-Yo related to the monomers) (Tab. 1). The copolymers were precipitated with methanol, filtered off and dried.The total content of monomeric units of 2 in the copolymers was obtained from the nitrogen analysis and the content of anthranyl groups was estimated from UV spectroscopy using the 390 nm absorption band.

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Copolymers with intramolecular charge transfer complexes (CTC) can be obtained by radical copolymerization of electron donor and electron acceptor monomer pairs'). The CT interactions were evidenced by electronic and NMR spectra and photoconductivity measurements2). This paper focuses on some solution properties of intramolecular CTC copolymers, namely p o l y [ Z~~~b~o l y l ) e t h y l methacry1ate-co-2-(methacryloyloxy)ethyl 3,5-dinitrobenzoate]. The conclusions can be extended to similar systems.

A new monomer, 4,5-dihydro-2-[2-(9-anthryl)ethyl]-1,3-OXa~Ok (5) was synthesized and polymerized by cationic ring-opening isomerization. The polymerization was carried out in bulk or in solution, using methyl tosylate, ethylene ditosylate and a-tosyl-w-tosyloxypoly(oxyethylene) [poly(ethylene oxide)ditosylate] as initiators. The polymers were characterized by IR, I H NMR and UV spectroscopy.