1：Experimental Design and Method Selection:

The study involved synthesizing derivatives of norbornadiene (NBD5) through chemical modifications at the C2 and C7 positions to tune properties for solar energy storage. Methods included reduction, Knoevenagel condensation, Meerwein-Wagner rearrangement, and elimination reactions.

2：Sample Selection and Data Sources:

NBD5 was used as the starting material, synthesized via literature methods. Derivatives were prepared and characterized.

3：List of Experimental Equipment and Materials:

Equipment included NMR spectrometers (Varian 400 MHz, Varian 500 MHz, Bruker 500 MHz), UV-vis spectrophotometers (Cary 60, Cary 100), DSC apparatus (Mettler Toledo DSC 2), IR spectrometer (Perkin-Elmer Frontier FT-IR), and HRMS (Agilent 1260 Infinity with APCI). Chemicals were purchased from commercial sources.

4：Experimental Procedures and Operational Workflow:

Synthesis steps involved reactions such as reduction with DIBALH, condensation with phosphonates, rearrangement with acetyl halides and aluminum trihalides, protection with ethylene glycol, and elimination with KOtBu. Products were purified by column chromatography and characterized by NMR, IR, UV-vis, and DSC. Photoswitching was performed using LED lamps (Thorlabs M365F1, M310L3, M340L4) and a TLC lamp (Vilber Lourmet).

5：Data Analysis Methods:

Kinetics were measured using UV-vis spectroscopy and analyzed with the Eyring equation. Quantum yields were measured using actinometry. DSC was used for energy storage measurements.