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An economical and effective protocol for large scale synthesis of the 2-phenyl-1,8adihydroazulene-1,1-dicarbonitrile (DHA) photoswitch has been developed. This compound is ring-opened by light to a vinylheptafulvene (VHF), which is thermally closed back to DHA. This compound serves as an important starting material for dihydroazulene photoswitches incorporating a substituent in the seven-membered ring and as a reference compound for comparison of properties. A detailed NMR spectroscopic characterization has allowed the assignment of all proton and carbon signals. In addition, the compound was characterized by Xray crystallography. A correlation between the rate constant for thermal ring-closure of VHF to DHA and empirical parameters of solvent polarity (ET30) was established.

Optimized synthesis and detailed NMR spectroscopic characterization of the 1,8a-dihydroazulene-1,1-dicarbonitrile photoswitch