Dynamic covalent synthesis of [2]- and [3]rotaxanes both in solution and on solid supports

Abstract

<p>Here we demonstrate the application of a dynamic covalent chemistry methodology for the synthesis of [2]- and [3]-rotaxanes not only in solution, but also on solid supports with 65% rotaxane functionalisation of the polymer resins observed.</p>

Sulfur in Dynamic Covalent Chemistry

“…In addition, under these conditions some supramolecular interactions such as hydrogen‐bond interactions are prominent, [56] and donor–acceptor catenanes [57] and rotaxanes such as 19 (Figure 5) were prepared in solution and on the solid phase [58] …”

Dynamic Covalent Chemistry for Synthesis and Co‐conformational Control of Mechanically Interlocked Molecules

“…Recently, Mullen and co‐workers explored dynamic covalent chemistry for the attachment of rotaxanes to polymer beads. Initially, NDI‐containing threads with thiol end groups and 1,5‐dinaphtho[38]crown‐10 macrocycle (DN38C10) were reacted with a thiol‐functionalized polymer resin [93] . After disulfide exchange, surface‐bound [2]rotaxanes were formed as a result of the templating donor‐acceptor interactions.…”

Sulfur in Dynamic Covalent Chemistry

“…[55] In addition, under these conditions some supramolecular interactions such as hydrogen-bond interactions are prominent, [56] and donor-acceptor catenanes [57] and rotaxanes such as 19 (Figure 5) were prepared in solution and on the solid phase. [58] Similar conditions were used to obtain macrocyclic (20), [59] macrobicyclic (21), and tetrahedral (22) [60] cyclophanes (Figure 5), as well as to functionalize single-walled carbon nanotubes with mechanically interlocked disulfide macrocycles equipped with π-extended tetrathiafulvalene motifs 23. [61] Recently, the Leclaire group used disulfide-based dyn-[n]arenes to warn about underestimating concentrations when HPLC is used for composition analysis.…”