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We describe the synthesis and characterization of novel diarylethene photoswitches that contain a norbornadiene bridge and operate as p-type positive photochromes. One of the double bonds of norbornadiene is furthermore utilized to attach a fluoresceine tetrazine by an iEDDA cascade reaction, thereby forming a turn-off mode fluorescent photoswitch.Transition metal-catalysed cross-coupling reactions are widely used for construction of carbon-carbon and carbon-heteroatom bonds. However, compared to aryl or alkenyl elect