Kukurbit[6]yuril ve porfirine dayalı rotaksan ve polyrotaksanlar

ABSTRACTROTAXANES AND POLYROTAXANES BASED ON CUCURBIT[6]URIL ANDPORPHYRINNESİBE CINDIRM.S. in ChemistrySupervisor: Asst. Prof. Dr. Donus TuncelAugust 2005In this study, the ability of CB[6] to catalyze 1,3-dipolar cycloaddition reactionbetween diazido and dialkyne functionalized trans substituted porphyrin monomers hasbeen investigated. The main objective of this work is to synthesize a novel polyrotaxanecontaining porphyrin and CB[6] as stopper and macrocycle respectively by the self-threading method.In the first part of the thesis, porphyrin containing monomers with diazido anddialkyne functional groups have been synthesized. These monomers have beencharacterized by FT-IR, UV-Vis, 1H NMR and 13C NMR. After they have beenprotonated, there have been changes in solubility and red shifts in the UV spectra.Although free base monomers are soluble in organic solvents, they are soluble in neitherorganic solvents nor water at high pH. However, they are soluble in acidic solutions atlow pHs.In the second part, before synthesis of polyrotaxanes, [3] rotaxane and [5]rotaxanes have been synthesized to model the properties and characterization ofpolyrotaxanes. Although [3] rotaxane has better solubility than monomers, its watersolubility was not good enough. However, [5] rotaxane is well soluble in water.Finally, after characterization of the rotaxanes with the same methods,polyrotaxanes have been synthesized and characterized. Although better water solubilitywith polymerization is expected, the water solubility has not improved. Additionally, it isexpected to have better solubility by replacement of one of the porphyrin containingmonomer to long aliphatic chain. However, there is also no improvement in solubility bythis technique.Keywords; Polyrotaxanes, rotaxanes, cucurbit[6]uril, 1,3-dipolar cycloaddition,porphyrin.