Two-stage directed self-assembly of a cyclic [3]catenane

Nature Chemistry

Volumn 7, Issue 4, 2015, Pages 354-358

  Wood, Christopher S ^a   Ronson, Tanya K ^a   Belenguer, Ana M ^a   Holstein, Julian J ^b,c   Nitschke, Jonathan R ^a  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

^b GLOBAL PHASING LTD   (United Kingdom)

^c UNIVERSITY OF GÖTTINGEN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84925802955     PISSN: 17554330     EISSN: 17554349     Source Type: Journal    
DOI: 10.1038/nchem.2205     Document Type: Article

References (35)

1. Evans, N. H. & Beer, P. D. Progress in the synthesis and exploitation of catenanes since the millennium. Chem. Soc. Rev. 43, 4658-4683 (2014).
2. Forgan, R. S., Sauvage, J. P. & Stoddart, J. F. Chemical topology: complex molecular knots, links, and entanglements. Chem. Rev. 111, 5434-5464 (2011).
3. Beves, J. E., Blight, B. A., Campbell, C. J., Leigh, D. A. & McBurney, R. T. Strategies and tactics for the metal-directed synthesis of rotaxanes, knots, catenanes, and higher order links. Angew. Chem. Int. Ed. 50, 9260-9327 (2011).
4. Ponnuswamy, N., Cougnon, F. B., Clough, J. M., Pantos, G. D. & Sanders, J. K. Discovery of an organic trefoil knot. Science 338, 783-785 (2012).
5. van Dongen, S. F., Cantekin, S., Elemans, J. A., Rowan, A. E. & Nolte, R. J. Functional interlocked systems. Chem. Soc. Rev. 43, 99-122 (2014).
6. Liang, C. Z. & Mislow, K. Topological chirality and achirality of links. J. Math. Chem. 18, 1-24 (1995).
7. Dean, F. B. & Cozzarelli, N. R. Mechanism of strand passage by Escherichia coli topoisomerase I. The role of the required nick in catenation and knotting of duplex DNA. J. Biol. Chem. 260, 4984-4994 (1985).
8. Takusagawa, F. & Kamitori, S. A real knot in protein. J. Am. Chem. Soc. 118, 8945-8946 (1996).
9. Rosengren, K. J. et al. Microcin J25 has a threaded sidechain-to-backbone ring structure and not a head-to-tail cyclized backbone. J. Am. Chem. Soc. 125, 12464-12474 (2003).
10. Duda, R. L. Protein chainmail: catenated protein in viral capsids. Cell 94, 55-60 (1998).
11. Quake, S. R. Topological effects of knots in polymers. Phys. Rev. Lett. 73, 3317-3320 (1994).
12. Saitta, A. M., Soper, P. D., Wasserman, E. & Klein, M. L. Influence of a knot on the strength of a polymer strand. Nature 399, 46-48 (1999).
13. Sauvage, J. P. Interlacing molecular threads on transition-metals-catenands, catenates, and knots. Acc. Chem. Res. 23, 319-327 (1990).
14. Ashton, P. R. et al. A [2]catenane made to order. Angew. Chem. Int. Ed. Engl. 28, 1396-1399 (1989).
15. Hunter, C. A. Synthesis and structure elucidation of a new [2]-catenane. J. Am. Chem. Soc. 114, 5303-5311 (1992).
16. Nierengarten, J. F., Dietrichbuchecker, C. O. & Sauvage, J. P. Synthesis of a doubly interlocked [2]-catenane. J. Am. Chem. Soc. 116, 375-376 (1994).
17. Mohr, B., Weck, M., Sauvage, J. P. & Grubbs, R. H. High-yield synthesis of [2]catenanes by intramolecular ring-closing metathesis. Angew. Chem. Int. Ed. Engl. 36, 1308-1310 (1997).
18. Lincheneau, C., Jean-Denis, B. & Gunnlaugsson, T. Self-assembly formation of mechanically interlocked [2]-and [3]catenanes using lanthanide ion [Eu(III)] templation and ring closing metathesis reactions. Chem. Commun. 50, 2857-2860 (2014).
19. Leigh, D. A., Pritchard, R. G. & Stephens, A. J. A star of David catenane. Nature Chem. 6, 978-982 (2014).
20. Chichak, K. S. et al. Molecular Borromean rings. Science 304, 1308-1312 (2004).
21. Ayme, J. F. et al. A synthetic molecular pentafoil knot. Nature Chem. 4, 15-20 (2012).
22. Hasenknopf, B., Lehn, J. M., Kneisel, B. O., Baum, G. & Fenske, D. Selfassembly of a circular double helicate. Angew. Chem. Int. Ed. Engl. 35, 1838-1840 (1996).
23. Allen, K. E. et al. Head-to-tail and heteroleptic pentanuclear circular helicates. Angew. Chem. Int. Ed. 49, 6655-6658 (2010).
24. Safont-Sempere, M. M., Fernandez, G. & Wurthner, F. Self-sorting phenomena in complex supramolecular systems. Chem. Rev. 111, 5784-5814 (2011).
25. Ayme, J. F., Beves, J. E., Campbell, C. J. & Leigh, D. A. The self-sorting behavior of circular helicates and molecular knots and links. Angew. Chem. Int. Ed. 53, 7823-7827 (2014).
26. Kramer, R., Lehn, J. M. & Marquis-Rigault, A. Self-recognition in helicate self-assembly: spontaneous formation of helical metal complexes from mixtures of ligands and metal ions. Proc. Natl Acad. Sci. USA 90, 5394-5398 (1993).
27. Riddell, I. A. et al. Five discrete multinuclear metal-organic assemblies from one ligand: deciphering the effects of different templates. J. Am. Chem. Soc. 135, 2723-2733 (2013).
28. Sarma, R. J. & Nitschke, J. R. Self-assembly in systems of subcomponents: simple rules, subtle consequences. Angew. Chem. Int. Ed. 47, 377-380 (2008).
29. De, S., Mahata, K. & Schmittel, M. Metal-coordination-driven dynamic heteroleptic architectures. Chem. Soc. Rev. 39, 1555-1575 (2010).
30. Schultz, D. & Nitschke, J. R. Designing multistep transformations using the Hammett equation: imine exchange on a copper(I) template. J. Am. Chem. Soc. 128, 9887-9892 (2006).
31. Tung, S. T., Lai, C. C., Liu, Y. H., Peng, S. M. & Chiu, S. H. Synthesis of a [2]catenane from the sodium ion templated orthogonal arrangement of two diethylene glycol chains. Angew. Chem. Int. Ed. 52, 13269-13272 (2013).
32. Peters, A. J., Chichak, K. S., Cantrill, S. J. & Stoddart, J. F. Nanoscale Borromean links for real. Chem. Commun. 3394-3396 (2005).
33. Chung, M.-K., Severin, K., Lee, S. J., Waters, M. L. & Gagné, M. R. Constitutionally selective amplification of multicomponent 84-membered macrocyclic hosts for (?)-cytidine·H+. Chem. Sci. 2, 744-747 (2011).
34. Dietrich-Buchecker, C., Leize, E., Nierengarten, J.-F., Sauvage, J.-P. & Van Dorsselaer, A. Singly and doubly interlocked [2]-catenanes: influence of the degree of entanglement on chemical stability as estimated by fast atom bombardment (FAB) and electrospray ionization (ESI) mass spectrometries (MS). J. Chem. Soc. Chem. Commun. 2257-2258 (1994).
35. Zhu, R., Lübben, J., Dittrich, B. & Clever, G. H. Stepwise halide-triggered double and triple catenation of self-assembled coordination cages. Angew. Chem. Int. Ed. 54, 2796-2800 (2015).