Organic/polymer semiconductors as new electronic materials have attracted scientific and industrial interest.The essential characteristic of organic semiconductors was the mobility of charge in the electron system.[1] According to the four element principle of designing organic/polymeric semiconductors:[2-3] the modification of molecules electric structure was the most basic tool to modulate the performance of devices through inserting various building block into the π-electron system.Here in,the cyclopropane as δ block model was inserted into the π-electron system.Ground geometric conformations were fully optimized at B97D/TZVP[4] level using Gaussian 09 program.[5] An integrated approach has been employed to estimate the electronic structures and optical properties.Compared with corresponding alkanes,olefins and 1,1-disubstituted cyclopropanes,the energy gap of 1,2-disubstituted cyclopropanes were between the corresponding alkanes and olefins and were larger than 1,1-disubstituted cyclopropane.The results also showed that the trans-isomers had higher symmetry than the cis-isomers in ground-state structures and electronic structures.The wavelength of absorption peaks of the trans-isomers was red-shift compared to the cis-isomers.Furthermore,When a negative charge was added and removed on the cis-1,2-diphenyl cyclopropane,the ring was opened and closed,respectively.These cyclopropane-based π-systems will be potential advanced organic semiconductors for the application of molecular and organic electronics as well as plastics mechatroncs.