A Six-Bowl Carceplex That Entraps Seven Guest Molecules

Abstract

A six-bowl carceplex that entraps seven guest molecules, 5.(DMSO)7, was synthesized and characterized. The dynamics of the host shell was studied in solution in the absence and presence of water. A multiple-molecule template was found to drive the formation of 5.(DMSO)x.G(7-x) (G = DMA, DMF; x = 5-7). Higher selectivity was found for species containing greater numbers of DMSO molecules.

One‐Pot, 18‐Component Synthesis of an Octahedral Nanocontainer Molecule

“…[5][6][7][8] The power of these supramolecular approaches is their ease and efficiency, best demonstrated in the quantitative synthesis of nanoscale capsules that are large enough to accommodate multiple guests. [9][10][11][12] Even though similar sized covalent container molecules, constructed from five or six cavitands, have been prepared in multiple steps, [13,14] an approach for their synthesis with efficiencies that are comparable to those of supramolecular approaches remains elusive. Herein, we report the nearly quantitative one-pot synthesis of a nanoscale container molecule by making use of dynamic covalent chemistry.…”

Trimeric and hexameric calixarene-based capsules

“…66·(DMSO) 7 . 64 It should be pointed out that this is a very large carceplex which is a covalent analogue of noncovalently bound pyrogallolarene hexamers. The NMR data and MM2 calculations indicate that 66·(DMSO) 7 has a slightly flattened, non symmetric structure; it reversibly complexes water molecules to give 66·(DMSO) 7 · (H 2 O) x ; x is not known.…”

“…It should be pointed out that for such a large container, and for guests of similar shape and polarity, this selectivity is very high. 64 In the second example the tetraformyl cavitand 67 was a starting material. It was observed that one-pot reactions of 67 with ethylene 1,2-diamine 68 lead to covalently bound capsules of a different shape, in dependence on the kind of solvent; in THF the tetramer 69, in CHCl 3 the hexamer 70 and in CH 2 Cl 2 the octamer 71 are formed 10,11 .Octamer 71 is a square antiprismatic capsule in which each cavitand occupies one of the eight corners 11 .…”

“…21 The efficient synthesis of capsules which are large enough to entrap various guests is a great challenge. 11,[22][23][24][25] Capsules are held together by weak noncovalent interactions, such as hydrogen…”

A simple one-pot multicomponent synthesis of an octahedral nanocontainer molecule

“…26). Our approach strongly surpasses earlier multistep covalent synthesis of related nanocontainers in its simplicity and efficiency, which should facilitate applications in medicinal, analytical, chemical and material sciences 27,28 . Important was the choice of imine bonds to connect building blocks during the synthesis.…”