A novel substituted cyclophane system which possesses two ethano and a single vinyl bridges in symmetrical fashion is considered for AM1 (RHF) type semiempirical calculations. The phane decks of this system are actually embedded phenol and benzylideneaniline moieties and they are also the constituents of salicylideneaniline structure which is the simplest photochromic dye. In this way, it has been investigated that how cyclophane structure affects the keto-enol tautomerism and UV-VIS spectra when these chromophores exist in a different structure than salicylideneaniline. The enol and keto forms of the resultant cyclophane system were found to be stable but endothermic being the enol form more favorable. The theoretical UV-VIS spectra of the tautomers were obtained and compared with salicylideneaniline tautomers. (C) 2003 Elsevier B.V. All rights reserved.