Telechelic thiopolymers were explored towards formation of doubly-bound (polymer loops) vs. singly-bound (polymer brushes) chains on gold substrates. The conformation, adsorption kinetics, and viscoelastic properties of the α,ω-dithiol and monothiol PS telechelics were investigated by means of XPS and QCM-D techniques. The oxidation behavior of the free thiol proved to be important for distinguishing doubly-bound vs. singly-bound chains. The results show a critical dependence of on the ability to obtain polymer loops. Comparison with unperturbed dimensions obtained by scaling theory show that the loop is less stretched and occupies more lateral space than the brush. The results are important in demonstrating the different and perhaps superior properties of polymer loops vs. singly-bound polymer brushes.