Unusual solid-state behavior in a neutral [2]catenane bearing a hydrolyzable component

Organic Letters

Volumn 6, Issue 5, 2004, Pages 655-658

  Fallon, Gary D ^a   Lee, Marcia A P ^a   Langford, Steven J ^a   Nichols, Peter J ^a  

^a MONASH UNIVERSITY   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

CATENANE; CROWN ETHER; DIMER; ESTER DERIVATIVE; MACROCYCLIC COMPOUND;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; HYDROLYSIS; ISOMER; NANOTECHNOLOGY; PHYSICAL CHEMISTRY; SAPONIFICATION; SOLID STATE; STRUCTURE ANALYSIS;

EID: 1642402831     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol036116s     Document Type: Article

References (24)

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19. For discussion of template-directed syntheses, see: Anelli, P.-L.; Ashton, P. R.; Ballardini, R.; Balzani, V.; Delgado, M.; Gandolfi, M. T.; Goodnow, T. T.; Kaifer, A. E.; Philp, D.; Pietraszkewicz, M.; Prodi, L. Reddington, M. V.; Slawin, A. M. Z.; Spencer, N.; Stoddart, J. F.; Vicent C.; Williams, D. J. J. Am. Chem. Soc. 1992, 114, 193 and references therein.
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21. This methodology has been employed previously in a [3]catenane; see: Asakawa, M.; Ashton, P. R.; Menzer, S.; Raymo, F. M.; Stoddart, J. F.; White, A. J. P.; Williams, D. J. Chem. Eur. J. 1996, 2, 877.
22. The process is most likely a circumrotation of the hydroquinone unit around the periphery of the NDI macrocycle, which requires the interruption to only one set of interactions. A broadening of the resonances attributable to the alkyl groups of component 4 below 220 K is consistent with the slowing down of this process on the NMR time scale.
23. -1. Crystallographic data (excluding structure factors) for 6 has been deposited with the Cambridge Crystallographic Data Centre as supplementary publications no. CCDC-220655. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB21EZ, UK (fax (+44)1223-336-033; e-mail deposit@ccdc.cam.ac.uk).
24. 2D was necessary as the solvent in order to solubilize the [2]catenane 6 under the reaction conditions. The solubility problems of the catenane are inherent in the bis(diimide) macrocycle, which has been difficult to isolate. It seems that isolation of these macrocycles in any useful quantity will require the catalytic reduction of the acetylenic bridging groups to improve the solubility.