Norbornadiene–quadricyclane (NBD-QC) photoswitches have been used as molecular storage materials for storing photoenergy. However, the energy storage lifetime of these materials is short, and their optical absorbance captures only a small portion of the solar spectrum. In this presentation, we describe the design and synthesis of NBD derivatives that are designed to have longer storage lifetimes and broader overlap with the solar spectrum. Our synthesis strategy employs the Diels-Alder reaction combined with a systematic investigation of various donor and acceptor groups on the diene and dienophile moieties. The results showed that water can improve the overall reaction yields and allow the reactions to proceed at relatively low temperatures. Moreover, the yield of reactions can be further improved by the use of microwave heating rather than traditional heating methods.

Synthesis of norbornadiene-based energy storage materials via Diels–Alder reactions

ACS Fall 2021

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