Creation, Properties, and Chemical Behavior of Saturn-Type C_<60> Complexes.

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In the recent studies on C_<60>, the direct conversion reactions of C_<60> with several reactants are almost. Our researches on C_<60> are characterized by the following points ; 1) the creation of Saturn-type complexes of C_<60> with the supermacrocyclic crown ethers, 2) the regioselective introduction of functional groups at the apical positions of the created Saturn-type complexes. We have designed two crown crown ethers (36-crown-4 and crown ether consisting of four 1,4-phenylene and ether units (1)) as the host molecules for the creation of Saturn-type complexes of C_<60> and accomplished their syntheses. We have found that 36-crown-4 is a potential host molecule for ammonium salts and reported (Syn. Commun., 30, 849-858 (2000)). But we have not yet obtained the obvious results about the inclusion of C_<60> with 36-crown-4 and crown ether consisting of four 1,4-phenylene and ether units (1) although we have tried the inclusion experiment under the several conditions. We have thoug … More ht the inclusion experiment fails by reason of the flexibility of two crown ethers, so we have designed a novel crown ether consisting of four 1,3-diethynylbenzene and ether units (2) and achieved its synthesis. In the synthetic route of 2, we have chosen the coupling reaction between benzene ring unit and triple bond unit with Pd catalyst as a final step to obtain the desired crown ether in higher yield. The inclusion behavior of C_<60> into the synthesized crown ether under the reflux for 1 hour in toluene has been observed by the measurement of electronic absorption spectrum. Furthermore, Job's plot and isosbestic point at xxxnm between C6-and host 2. provided evidence for 1 : 1 complex in solution. The association constant of the inclusion complexes was determined from the difference of absorbance at 430-440 nm region using Rose and Drago method. We will report the results to J.Am.Chem.Soc. as the article titled "Synthesis of Supermacrocycles and its Saturn type Supramolecular Entity with C_<60>". Less