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Recent synthetic advances allowing large-scale preparation and systematic functionalization of the dihydroazulene (DHA)-vinylheptafulvene (VHF) photo-/thermoswitch have enabled detailed studies on how to tune optical and switching properties and have paved the way for using this system as a functional unit in molecular electronics and materials chemistry. Since discovery of its photochromism in the 1980'ies, numerous examples of DHA-VHF systems have been developed, allowing multimode switching, fluorescence-control and fine tuning of absorbance and VHF half-lives, giving insights into the mechanism of the switching event. Here, we present an overview of the properties of the DHA-VHF system, together with some selected synthetic procedures which have paved the way for its development.

Dihydroazulene: from controlling photochromism to molecular electronics devices