Honing up a genre of amphiphilic bistable [2]rotaxanes for device settings

European Journal of Organic Chemistry

Volumn , Issue 1, 2004, Pages 196-220

  Jeppesen, Jan O ^a   Nygaard, Sune ^a   Vignon, Scott A ^b   Stoddart, J Fraser ^b  

^a UNIVERSITY OF SOUTHERN DENMARK   (Denmark)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Electrochemistry; Kinetics; Molecular shuttles; Molecular switches; Rotaxanes; Tetrathiafulvalenes

Indexed keywords

(MONOPYRROLO)TETRATHIAFULVALENE; 1,5 DIOXYNAPHTHALENE; AMPHOPHILE; CYCLOBIS(PARAQUAT 4 PHENYLENE); CYCLOPHANE; NAPHTHALENE DERIVATIVE; PARAQUAT; ROTAXANE; TETRATHIAFULVALENE DERIVATIVE; UNCLASSIFIED DRUG;

ABSORPTION SPECTROSCOPY; ARTICLE; CHEMICAL REACTION KINETICS; COMPLEX FORMATION; DEVICE; ELECTROCHEMISTRY; HYDROPHOBICITY; MASS SPECTROMETRY; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS; THERMODYNAMICS;

EID: 11944269170     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200400530     Document Type: Article

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127. [15b] J. O. Jeppesen, K. A. Nielsen, J. Perkins, S. A. Vignon, A. Di Fabio, R. Ballardini, M. T. Gandolfi, M. Venturi, V. Balzani, J. Becher, J. F. Stoddart, Chem. Eur. J. 2003, 9, 2982-3007.
128. 4+ was followed by correlating the maximum absorptions of the CT bands with the absolute concentrations of the components as described in M. B. Nielsen, J. O. Jeppesen, J. Lau, C. Lomholt, D. Damgaard, J. P. Jacobsen, J. Becher, J. F. Stoddart, J. Org. Chem. 2001, 66, 3559-3563.
129. J. O. Jeppesen, J. Perkins, J. Becher, J. F. Stoddart, Org. Lett. 2000, 2, 3547-3550.
130. [18a] J. O. Jeppesen, K. Takimiya, F. Jensen, J. Becher, Org. Lett. 1999, 1, 1291-1294.
131. [18b] J. O. Jeppesen, K. Takimiya, F. Jensen, T. Brimert, K. Nielsen, N. Thorup, J. Becher, J. Org. Chem. 2000, 65, 5794-5805.
132. C. Jia, D. Zhang, X. Guo, S. Wan, W. Xu, D. Zhu, Synthesis 2002, 2177-2182.
133. ++) are favored by high pressure, see: F.-G. Klärner, F. Wurche, J. Prakt. Chem. 2000, 342, 609-636.
134. [21a] D. Philp, A. M. Z. Slawin, N. Spencer, J. F. Stoddart, D. J. Williams, J. Chem. Soc., Chem. Commun. 1991, 1584-1586.
135. [21b] W. Devonport, M. A. Blower, M. R. Bryce, L. M. Goldenberg, J. Org. Chem. 1997, 62, 885-887.
136. [21c] See: a) ref.[16]. [21d] R. Ballardini, V. Balzani, A. Di Fabio, M. T. Gandolfi, J. Becher, J. Lau, M. B. Nielsen, J. F. Stoddart, New J. Chem. 2001, 25, 293-298.
137. [22a] P. R. Ashton, R. Ballardini, V. Balzani, S. E. Boyd, A. Credi, M. T. Gandolfi, M. Gómez-López, S. Iqbal, D. Philp, J. A. Preece, L. Prodi, H. G. Ricketts, J. F. Stoddart, M. S. Tolley, M. Venturi, A. J. P. White, D. J. Williams, Chem. Eur. J. 1997, 3, 152-170.
138. [22b] R. Wolf, M. Asakawa, P. R. Ashton, M. Gómez-López, C. Hamers, S. Menzer, I. W. Parsons, N. Spencer, J. F. Stoddart, M. S. Tolley, D. J. Williams, Angew. Chem. 1998, 110, 1018-1022; Angew. Chem. Int. Ed. 1998, 37, 975-979.
139. [22b] R. Wolf, M. Asakawa, P. R. Ashton, M. Gómez-López, C. Hamers, S. Menzer, I. W. Parsons, N. Spencer, J. F. Stoddart, M. S. Tolley, D. J. Williams, Angew. Chem. 1998, 110, 1018-1022; Angew. Chem. Int. Ed. 1998, 37, 975-979.
140. [22c] V. Balzani, A. Ceroni, A. Credi, M. Gómez-López, C. Hamers, J. F. Stoddart, R. Wolf, New J. Chem. 2001, 25, 25-31.
141. 4+, see: K. N. Houk, S. Menzer, S. P. Newton, F. M. Raymo, J. F. Stoddart, D. J. Williams, J. Am. Chem. Soc. 1999, 121, 1479-1487.
142. M. Asakawa, W. Dehaen, G. L'abbé, S. Menzer, J. Nouwen, F. M. Raymo, J. F. Stoddart, D. J. Williams, J. Org. Chem. 1996, 61, 9591-9595.
143. K. J. Laidler, Chemical Kinetics, Harper Collins Publisher, New York, 1987.
144. For further details, see the Exp. Sect.
145. At each temperature, first-order kinetics are obeyed, i.e., good straight lines are observed (see Table 4) when In A is plotted against t, where A is absorbance (at 807 nm) at time t. This outcome is a consequence of the fact that the data points were collected in the early stages of the experiments where the reverse process is not yet occurring to any significant extent.
146. B is the Boltzmann constant.
147. -1.
148. 3 signals for the complexed and complexed forms. The chemical shifts, line widths and integrations were used as input and determined from the low temperature spectrum where no exchange is observed. Simulation of the spectra using the Spinworks program (Spinworks Version 1.3, K, Marat, University of Manitoba, Department of Chemistry) gave the data reported in Table 5.
149. J. O. Jeppesen, S. A. Vignon, J. F. Stoddart, Chem. Eur. J. 2003, 9, 4611-4625.
150. K. A. Connors, Binding Constants, Wiley Interscience, New York, 1987.
151. 4+ ring. Such an SMe group resonates at a chemical shift higher than δ = 2.6 ppm, whereas an "uncomplexed" SMe group has a chemical shift of about δ = 2.40 ppm. See:a)ref.[l5]; b)ref.[17].
152. 4+ resonate at δ = 6.09 and 7.85 ppm, respectively.
153. a where R is the gas constant and T is the absolute temperature.
154. 4+), R is the gas constant and T is the absolute temperature.
155. V. Balzani, A. Credi, G. Mattersteig, O. A. Matthews, F. M. Raymo, J. F. Stoddart, M. Venturi, A. J. P. White, D. J. Williams, J. Org. Chem. 2000, 65, 1924-1936.
156. The distinction between rotaxanes and pseudorotaxanes is far from being a straightforward one. When size-complementarity between the stoppers and the macrocyclic component is achieved, certain "rotaxanes" behave as pseudorotaxanes and can dissociate into their constituent components under appropriate conditions. Thus, a species which is a rotaxane at ambient temperature might well be a pseudorotaxane at elevated temperatures. Even a solvent change can turn a rotaxane into a pseudorotaxane at the same temperature. See] [38a] F. M. Raymo, J. F. Stoddart, C9-). c-v. 1999, rr, 1643-1663.
157. [38b] S.-H. Chiu, S. J. Rowan, S. Cantrill, P. T. Glinj, R. L. Garrell, J. F. Stoddart, Tin P-yy. 2000, 0, 3631-3634.
158. [38[] A. Affeld, G. M. Hubner, C. Seel, C. A. Schalley, Fut. N T tn C9-). 2001, 2877-2890.
159. [38d] J. O. Jeppesen, J. Becher, J. F. Stoddart, T tn. P-yy. 2002, m, 557-560.
160. 2CO, see] [39a] A. Miryoian, A. E. Kaifer, N T tn C9-). 1995, u0, 8093-8095.
161. [39b] Ref.[15b].
162. 4+.
163. [40a] M. Asajawa, P. R. Ashton, V. Balvani, A. Credi, G. Mattersteig, O. A. Matthews, N. Montalti, N. Spencer, J. F. Stoddart, M. Venturi, C9-). Fut. N 1997, 3, 1992-1996.
164. [40b] M. Asajawa, P. R. Ashton, V. Balyani, S. E. Boyd, A. Credi, G. Mattersteig, S. Menyer, M. Montalti, F. M. Raymo, C. Ruffilli, J. F. Stoddart, M. Venturi, D. J. Williams, Put. N T tn. C9-). 1999, 985-994.
165. 4+ ring has previou4sly been observed in both bistable [2]rotaxanes and [2]pseudorotaxanes incorporating an MPTTF unit and a DNP moiety on the rod-section of its dumbbell component, see] [41a] ref.[15b]. [41b] ref.[31]. [41[] I. C. Lee, C. W. Franj, T. Zamamoto, H.-R. Tseng, A. H. Flood, J. F. Stoddart, J. O. Jeppesen, Pf. n) ult 2004, 00, 5809-5828.
166. 4+ encircles the TTF unit. However, this translational isomer exists as a 413lytf. 3 isomeric mixture.
167. D. D. Perrin, W. L. F. Armarego, aut 1k14f yls. sk Pf 5stf ysty C9-) 14f (3, Pergamon Press, New Zorj, 1944.
168. A. L. Van Geet, A. f(.C9-). 1970, m0, 679-680.
169. 7 was 0.93 mM.
170. S. F. Nelsen, L.-J. Chen, M. T. Ramm, G. T. Voy, D. R. Powell, M. A. Aceola, T. R. Seehafer, J. J. Sabeljo, J. R. Pladyiewicy, N T tn C9-). 1996, u7, 1405-1412.
171. [47a] M. Feigel, H. Kessler, D. Leibfrity, N A). C9-). Ss4. 1979, 707, 1943-1950.
172. [47b] B. E. Mann, N R fn. . c-3s. . 1977, 01, 91-94.