End-Capping of a Pseudorotaxane via Diels−Alder Reaction for the Construction of C₆₀-Terminated [2]Rotaxanes

Abstract

[reaction: see text] The Diels-Alder reaction of various dienophiles such as C(60) with a pseudorotaxane having a sultine moiety afforded corresponding [2]rotaxanes in moderate yields. The introduction of a porphyrin moiety on the wheel component considerably enhanced the efficiency of the end-capping reaction with C(60).

Photoinduced electron transfer processes in three component rotaxanes with porphyrins, [60]fullerene and triphenylamine

“…For preparative high performance liquid chromatography (HPLC), a JAICO LC-908 system using columns JAIGEL 1 and 2 was employed. Compounds 5, 6, 11, 13 and 14 were prepared according to the methods described in the literature [22][23][24][25][26][27][28].…”

Fullerene-Stoppered Bistable Rotaxanes

“…A different type of fullerene-stoppered bistable rotaxane is driven by exploiting the recognition between ammonium salts and crown ethers (Scheme 10) [23,24]. Rotaxane 9 displays a fullerene-stoppered thread with an ammonium salt.…”

Structure and Dynamic Behavior of Organometallic Rotaxanes

“…The pseudorotaxanes of dialkylammonium and DB24C8 have been used for this purpose because of their high association constant in the solvent with lower polarity. Many bond-forming reactions, such as esterification [26], urethane formation [27], Wittig reaction [27], hydrosilylation [29], propargylic substitution [30], Sonogashira coupling [31], cycloaddition [32], and Diels-Alder reaction [33], have been used for the threadingfollowed-by-end-capping method. In most of these reports, reactions that take place under neutral or acidic conditions were chosen to prevent the ammonium group from being neutralized.…”