Reversible Photoisomerization of Norbornadiene-Quadricyclane within a Confined Capsule^†

With the desire to develop a sustainable green method to store and release solar energy via a chemical reaction, we have examined the well-investigated norbornadiene-quadricyclane (NBD-QC) system in water. In this context, we have employed octa acid (OA) as the host that forms a capsule in water. According to ¹ H NMR spectra and diffusion constants, OA forms a stable 2:2 complex with both NBD and QC and 1:1:2 mixed complex in the presence of equal amounts of both NBD and QC. The photoconversion of NBD to QC within the OA capsule is clean without side reactions. In this case, OA itself acts as a triplet sensitizer. Recognizing the disadvantage of this supramolecular approach, in the future we plan to look for visible light absorbing sensitizers to perform this conversion. The reverse reaction (QC to NBD) is achieved via electron transfer process with methylene blue as the sensitizer. This reverse reaction is also clean, and no side products were detected. The preliminary results reported here provide "proof of principle" for combining green, sustainable and supramolecular chemistries in the context of solar energy capture and release.