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Need an account? Click here to sign up. Download Free PDF. Structural and co-conformational effects of alkyne-derived subunits in charged donor-acceptor [2] catenanes. Structural and co-conformational effects of alkyne-derived subunits in charged donor-acceptor [2] catenanes Journal of the …, William Dichtel.

A short summary of this paper. Oligoether chains carrying terminal alkynes or azides were used as the key structural features in template-directed cyclizations of [2]pseudorotaxanes to give the [2]catenanes. Both reactions proceed well with precursors of appropriate oligoether chain lengths but fail when there are only three oxygen atoms in the oligoether chains between the DNP units and the reactive functional groups.

Variable- temperature 1H NMR spectroscopy has been used to identify and quantify the barriers to the conformationally and co-conformationally dynamic processes. The barriers for the three processes were found to be successively Introduction and reversible molecular switching. Although a synthetic targets to potentially broadly applicable chemical 3 a Lindsey, J.

New J. Synlett , University of California. Collin, J. A third approach, that of tandem heterocatenation Figure 2c , can be proposedsand has indeed been realized in both neutral and charged donor-acceptor catenanes16sin which the formation of the donor and the acceptor rings happen concurrently.

While undoubtedly elegant, tandem heterocatena- tion remains underutilized synthetically because of its disap- pointing yields thus far and is relatively unexplored mecha- 6 a Luo, Y.

Science , , A , 80, Faraday Discuss. B , , Nature , , London Ser. A , , Molecular Switches; Wiley- Figure 1. Two ways Figure 2 of synthesizing donor- 10 a Doddi, G.

Assuming , 70, For electron-rich biphenyls, see: For neurotransmitters Pure Appl. Reddington, M. Stoddart, J. Supramolecular Chem. Nelson, A.

Svenstrup, N. VCH: Weinheim, Flood, A. For early examples of a Stoddart, J. Mater Chem. Nature , , g Dietrich-Buchecker, C. Tetrahedron Since it has not been strictly proven that both rings While these disadvantages restrict the synthetic options, they form simultaneously during the course of this reaction, it is certainly do not eliminate them entirely.

Hence, reactions have possible that tandem heterocatenation still proceeds via a been sought after that employ neutral or mildly acidic , cyclization-templation-catenation cascade, but with the dif- oxidative, and nucleophile-free conditions.

Both the click ference that either the donor or the acceptor can take on the reaction18 and Eglinton coupling19 were selected as promising role of the template with the outcome being identical.

This been confirmed experimentally,17 although this species is paper presents an examination of the scope and limitations of normally not isolated.

Finally, dynamic 1H NMR spectroscopic investigations show the de- pendence of conformational and co-conformational freedom on the size and nature of the [2]catenanes and allow us to identify and quantify the barriers to several dynamic processes occurring in the new catenated compounds.

Alternative strategies in the template-directed synthesis of charged 18 a Rostovtsev, V. Alternative heterocatenation strategies are i threading Siemsen, P. For the original report, see: b Eglinton, G. London , See: a Meissner, U. Synthesis, , The SO dianion is virtually nonnucleophilic, while the AcO- anion has strain in the cyclophane facilitates nucleophilic attack at the weak nucleophilic character which did not present a significant problem benzylic positions, displacing the positively charged bipyri- in our experiments.

Finally, basic conditions appear to be equally J. Tetrahedron of the benzylic methylene group leads to a number of rearranged Lett. Heath, J. Asian J. Ven, V. The based on donor-acceptor Sanders, Gunter ,27 transition metal- tolerance of complex formation under the conditions of the click ligand Sauvage ,28 and transient covalent bond Godt 29 tem- reaction is noteworthy, and this mild reaction has found use in plating strategies.

On a fundamental level, this result monotosylates31 which are then subjected to nucleophilic demonstrates that copper acetylides as the proposed mechanistic substitutions with sodium azide to produce the azides 7a-c.

This realization readily translated into the challenge to DMF or MeCN gave Scheme 2 intensely purple-colored synthesize [2]catenanes and prompted our investigations of the utility of the Eglinton oxidative alkyne homocoupling,19 another Scheme 2 reaction proceeding through intermediate copper acetylides.

B; Fokin, V. Rapid Commun. Macromolecules , 39, Subjecting these [2]pseudorotaxanes to Int. Macromolecules , 38, Macromolecules J. Tetrahedron , 62, Macromolecules , 39, J. For 6b and 6c, see: b Ashton, P. See, Chem. Synthesis , 19, Crystal, unit cell, be recovered, following the dethreading that undoubtedly occurs refinement, and some of the common structural parameters for during chromatography. Conversion of 9 to the corre- crystallographic center of inversion. Aside from the 4PF6, in which one of the oligoether chains emanating from PF6- counterions, hydrogen atoms and solvent molecules are omitted for the DNP unit is reflected through the plane of the naphthalene clarity.

Acceptor ring thus bringing the two triple bonds close to each other, the ring is shown in blue, donor thread in red, and triple bonds in purple. The oligoether chains are simply too short to cyclize to give a single pair of enantiomeric molecules36 in the unit cell and a polyether loop that would not be unreasonably strained. See: Northrop, B. Science , Chem. Wathey, B. Tetrahedron Lett. Instead, [2]catenane molecules pack around the butadiyne units.

Additionally, the two planes are nearly parallel 7. The Cambridge Structural Database CSD reports three structures that include formally both the pyridinium ring and the 1,2,3- triazole unit, the former being incorporated into an N-pyridinium oxide unit, the latter into a benztriazole system. Aside from the disordered PF6- helical chirality, such that molecules with P and M helicities can be counterions, hydrogen atoms and solvent molecules are omitted for clarity.

Acceptor ring is their symmetry elements once incorporated into a macrocycle. This shown in blue, donor thread in red, and triazole ring in purple. X-ray crystallography, and 1H NMR spectroscopy proximately parallel with the electron-poor inner bipyridinium reveal evidence for the existence of only one enantiomeric pair in the solid and solution states, respectively. Heterocycles , 55, Hexafluorobenzene, for example, stacks efficiently with one of the butadiyne subunits of dehydrobenz[12]annulene42 with an average distance between the aromatic plane and the atoms of the CtC-CtC chain of 3.

Curi- Figure 6. Acceptor ring is the closest point of contact, with a centroid-centroid distance shown in blue, donor ring in red, and butadiyne moiety in purple.


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