Multi-photochromic systemsi ncorporating individually addressables witching units are attractivef or development of advanced data storaged evices.H ere, we present the synthesis and properties of as election of such molecular systemsi ncorporating the dihydroazulene/vinylheptafulvene (DHA/VHF) photo-/thermoswitch. The influence of the linker (meta-phenylene vs. azulene-1,3-diyl vs. thiophene-2,5-diyl) separating two DHA units on the switching properties was investigated. An azulene-1,3-diyl spacer largely inhibited both the DHA-to-VHF photoisomerizations and the thermal VHF-to-DHA back-reactions;t he latter occurred ten times slower than for the related compound with a meta-phenyl-ene spacer.ADHA trimerc ontaining three DHA units aroundacentral benzene ring was found to undergo stepwise DHA-to-VHF photoisomerizations, whereas the thermal back-reactions occurred at similar rates for the three VHF entities.Ameta-phenylene-bridgedD HA dimerw as subjected to furthers tructural modifications at positionC-1 of each DHA,h avings trong implications for the switching events, and synthetic steps for further functionalizations at position C-7 of each DHA were investigated.F inally,t he molecular structure (from X-ray crystallographic analysis) between the meta-phenylene-bridgedDHA dimer and Cu I is presented.