‘Ship-in-a-Bottle’ Synthesis and Photochromism of Spiropyrans Encapsulated within Zeolite Y Supercages

The ship-in-a-bottle synthesis of three spiropyrans inside the NaY supercages was carried out by the condensation of 2-methylene-1,3,3-trimethylindoline with the appropriate substituted benzaldehyde. After the reaction, spiropyrans were detected in the supernatant and the zeolites became coloured. Combustion chemical and thermogravimetric analyses confirmed the presence of organic material within the solid. UV–Vis and Raman spectroscopies are compatible with the formation of the merocyanine form of the spiropyran photochromic system. Upon visible irradiation the solids bleach, and in some cases the coloration is regained upon standing in the dark for long periods. This abnormal photochromic behaviour is the reverse of that observed for the spiropyran/merocyanine system in ethanol and illustrates the possibility of zeolites as media to alter the molecular properties of incorporated guests.