K. Kishi et al., SYNTHESIS OF SOLAR-ENERGY STORAGE-EXCHANG E POLYMER CONTAINING CHALCONE TYPE NORBORNADIENE MOIETY AND PHOTOCHEMICAL-REACTION OF THE RESULTING POLYMER, Kobunshi ronbunshu, 51(5), 1994, pp. 295-302
A chalcone type norbornadiene (NBD) derivative was prepared by Diels-A
lder reaction of cyclopentadiene with an acethylene compound which was
synthesized from 4'-hydroxychalcone. Chalcone type NBD polymer was sy
nthesized by the resulting NBD derivative with poly(p-chloromethylstyr
ene). The photochemical reaction of the polymer thus obtained was eval
uated in the film state. The photochemical valence isomerization of th
e chalcone type NBD polymer proceeded to produce the corresponding qua
dricyclane (QC) groups with 60 second irradiation with a 500 W-xenon l
amp. Furthermore, it was found that the rate of photochemical valence
isomerization of the chalcone type NBD polymer was higher than that of
the other NBD polymers having phenyl or N-phenylcarbamoyl groups as c
hromophores. The reversion from the QC groups to the NBD moieties in t
he polymer was carried out using 5,10,15,20-tetraphenyl-21H,23H-porphi
necobalto(II) (Co-TPP) as a catalyst in THF solution. The catalytic re
version proceeded very smoothly. The thermal reversion from QC groups
to NBD moieties in the film state also proceeded smoothly.