Formation of a chain-end-free surface on a self-assembled monolayer of a cyclic disulfide

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Cyclic alkanedisulfides were synthesized from linear alkanedithiols consisting of 10 and 20 carbon atoms using a bromo-Wang resin. The size of the macrocycles was determined by SEC measurements. While an alkanedithiol consisting of 20 carbon atoms mainly produced monomeric, dimeric, and trimeric macrocycles with a decreasing yield as the increasing size of the macrocycle, that of 10 carbon atoms resulted in the formation of only dimeric and higher macrocycles.