A mechanically active spiropyran (SP) mechanophore is incorporated into the backbone of prepolymer which is further end-capped with ureidopyrimidinone (UPy) or urethane. Strong mechanochromic reaction of SP arises in the bulk films of UPy containing materials whereas much weaker activation occurs in urethane containing counterparts, coincident with their stress鈥搒train responses. The difference in the magnitudes of supramolecular interactions leads to different degrees of chain orientation and strain induced crystallization (SIC) in the bulk and consequently distinct capabilities to transfer the load to the mechanophores. This study may aid the design of novel mechanoresponsive materials whose mechanoresponsiveness can be tailored by tuning supramolecular interactions.