Conjugated macrocycles are attractive precursors to new materials such as porous solids, synthetic ion channels, catalysts and other supramolecular materials. The development of these cyclic molecules for applications has been limited by the synthetic difficulties inherent in assembling a complex molecule. Imine formation by the condensation of amine and an aldehyde is a convenient method for assembling large molecules. Since this reaction is reversible, macrocycles can be obtained under thermodynamic control. [2+2] conjugated macrocycles was prepared by employing Schiff-base chemistry without the necessity of an added template. This new macrocycles contain two N 2 O 2 pockets, which can bind to multiple metal ions (e.g. Zn 2+ ) . The fluorescence of the macrocycle could also be quenched by the coordination of metal ions (e.g. Ni 2+ ) in the two pockets. In the second part of project, we used 2,3-phenazine diamine and react it with salicylaldehyde and 3,5-di(t-buthyl)-2-hydroxy benzaldehyde to synthesis Jacobsen type salphenes. All compounds were characterized by 1 H NMR, FT-IR, UV, elemental analysis. Ionic salphen been synthesized by reacting the salphene with methyl iodide. Ionic salphen metalized obtained by reacting of salphen Mn(III) with methyl iodide and used in styrene epoxidation reaction.