A Chemically and Electrochemically Switchable [2]Catenane Incorporating a Tetrathiafulvalene Unit

Angewandte Chemie - International Edition

Volumn 37, Issue 3, 1998, Pages 333-337

  Asakawa, Masumi ^a   Ashton, Peter R ^a   Balzani, Vincenzo ^b   Credi, Alberto ^b   Hamers, Christoph ^a   Mattersteig, Gunter ^a   Montalti, Marco ^b   Shipway, Andrew N ^a   Spencer, Neil ^a   Stoddart, J Fraser ^a,d   Tolley, Malcolm S ^a   Venturi, Margherita ^b   White, Andrew J P ^c   Williams, David J ^c  

^a UNIVERSITY OF BIRMINGHAM   (United Kingdom)

^b UNIVERSITY OF BOLOGNA   (Italy)

^c IMPERIAL COLLEGE LONDON   (United Kingdom)

^d UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Catenanes; Charge transfer complexes; Molecular devices; Redox switching; Self assembly; Supramolecular chemistry

Indexed keywords

EID: 0032536465     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19980216)37:3<333::AID-ANIE333>3.0.CO;2-P     Document Type: Article

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41. - anions, and the included MeCN molecules were refined anisotropically; due to a shortage of observed data, the non-hydrogen atoms of the tetracation were refined isotropically. Crystallographic data (excluding structure factors) for the structure reported in this paper have been deposited with the Cambridge Crystallographic Data Center as supplementary publication no. CCDC-100460. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB21EZ (fax: int. code + (44) 1223336-033; e-mail: deposit@ccdc.cam.ac.uk).
42. 10O vector of the "alongside" 1,5-dioxynaphthalene moiety is inclined by 18° to the mean plane of the tetracation.
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49. The mean interplanar separations betwien the "inside" disubstituted TTF ring system and the "inside" and "alongside" bipyridinium units are 3.43 and 3.37 Å, respectively; the separation between the "along-side" 1,5-dioxynaphthalene moiety and the "inside" bipyridinium unit is 3.31 Å. Hydrogen bonds between α-bipyhdinium hydrogen atoms on the "inside" bipyridinium unit and the two polyether oxygen atoms have the following geometries: [C ⋯ O] 3.39 and 3.12 Å, [H ⋯ O] 2.43 and 2.40 Å; C-H ⋯ O angles 174° and 132°. The diametrically opposite sulfur atoms adjacent to the "trans"-substituted carbon atoms lie about 3.6 Å from the centroids of their proximal paraxylylene rings.
50. 3CN, 31°C, 20U ms mixing time), which display cross-peaks between the OCH: protons attached to the TTF core, and both the a-bipyridinium and the p-xylyl protons of the tetraeaiionic cyclo- phane. No cross-peaks could be observed indicating that none of the 1.5-dioxynaphthalene moiety is located inside!
51. 5+ in a 2:1 ratio shows a peak at m/z = 898 as the most abundant in the spectrum. This peak corresponds to the incorporation of one counterion derived from o-chloranil into the [2]catenane. Once again, this species was found to be doubly charged by examination of isotopic abundances. Additionally, the spectrum shows peaks at m/s = 775 and 468. These peaks are the major ones for a sample recorded after standing for one week. The isotopic separations of these ions confirm that they are doubly (m/z = 775) and triply (m/z = 468) charged species. None of the spectra obtained show evidence for the presence of a monocationic species. As expected with reference to the second oxidation potential of the crown ether 3, oxidation with o-chloranil yields preferentially Sfi~. We would like to thank one of the referees for asking us to comment on the nature of the oxidation state of the TTF unit.
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54. The electrochemical experiments were carried out in argon-purged MeCN solutions with a Princeton Applied Research 273 multipurpose instrument interfaced to a personal computer, with cyclic voltammetry and differential pulse voltammetry techniques. The exact configuration and procedures for these measurements have been reported in Ref. [5e].
55. A detailed study of the interesting electrochemical behavior of crown ether 3 will be reported elsewhere.
56. The alternative explanation, based on lack of reversibility of the electrode process due to restricted access to the inside TTF unit, can be ruled out on consideration of the behavior observed for all the catenanes and rotaxanes previously investigated. See, for example: a) Ref. [5b]; b) P. R. Ashton, R. Ballardini, V. Balzani, M. Belohradsky, M. T. Gandotfi, D. Philp, L. Prodi, F. M. Raymo, M. V. Reddington, N. Spencer, J. F. Stoddart, M. Venturi, D. J. Williams, J. Am. Chem. Soc. 1996, 118, 4931-4951.
57. The alternative explanation, based on lack of reversibility of the electrode process due to restricted access to the inside TTF unit, can be ruled out on consideration of the behavior observed for all the catenanes and rotaxanes previously investigated. See, for example: a) Ref. [5b]; b) P. R. Ashton, R. Ballardini, V. Balzani, M. Belohradsky, M. T. Gandotfi, D. Philp, L. Prodi, F. M. Raymo, M. V. Reddington, N. Spencer, J. F. Stoddart, M. Venturi, D. J. Williams, J. Am. Chem. Soc. 1996, 118, 4931-4951.
58. We have found that oxidation of a 1,5-dioxynaphthalene moiety in alongside" and "inside" positions occurs at +1.30 and +1.55 V vs SCE. respectively, in a catenane made of the cyclobis(paraquat-pphenylene) tetracation and a crown ether (1/5DN38C10) containing two 1,5-dioxynaphthalene moieties.
59. 6+), with their different oxidation states, are not isomers, we have introduced quotation marks round the term isonier(s) in our discussion of these two catenated species.