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A new azobenzene-thiophene molecular switch is designed, synthesized and usedto form self-assembled monolayers (SAM) on gold. An "on/off" conductance ratioup to 7x1E3 (with an average value of 1.5x1E3) is reported. The "on"conductance state is clearly identified to the cis isomer of the azobenzenemoiety. The high "on/off" ratio is explained in terms of photo-induced,configuration-related, changes in the electrode-molecule interface energetics(changes in the energy position of the molecular orbitals with respect to theFermi energy of electrodes) in addition to changes in the tunnel barrier length(length of the molecules). First principles DFT calculations demonstrate abetter delocalization of the frontier orbitals, as well as a strongerelectronic coupling between the azobenzene moiety and the electrode for the cisconfiguration over the trans one. Measured photoionization cross-sections forthe molecules in the SAM are close to the known values for azobenzenederivatives in solution.

High on-off conductance switching ratio in optically-driven self-assembled conjugated molecular systems