Structural and co-conformational effects of alkyne-derived subunits in charged donor-acceptor [2]catenanes

Journal of the American Chemical Society

Volumn 129, Issue 26, 2007, Pages 8236-8246

  Miljanić, Ognjen Š ^a   Dichtel, William R ^a,b   Khan, Saeed I ^a   Mortezaei, Shahab ^a   Heath, James R ^b   Stoddart, J Fraser ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b California Institute of Technology   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLIZATION; CYCLOADDITION; DERIVATIVES; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POLYETHERS; SYNTHESIS (CHEMICAL);

ALKYNES; CYCLOPHANE; ELECTRON DONOR RINGS; OLIGOETHER CHAINS;

HYDROCARBONS;

2,4 DINITROPHENOL; ALKYNE DERIVATIVE; AZIDE; BENZENE DERIVATIVE; BIPYRIDINE DERIVATIVE; CATENANE; COPPER; CYCLOPHANE; FUNCTIONAL GROUP; MACROCYCLIC COMPOUND; NAPHTHALENE DERIVATIVE; PARAQUAT; POLYETHER; TAXANE DERIVATIVE; TRIAZOLE DERIVATIVE;

ARTICLE; BINDING SITE; CATALYSIS; CHEMICAL STRUCTURE; CONFORMATION; CYCLOADDITION; DIPOLE; MOLECULAR DYNAMICS; MOLECULAR INTERACTION; MOLECULAR STABILITY; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOSPECIFICITY; SYNTHESIS;

EID: 34447130381     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja071319n     Document Type: Article

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156. (a) Katritzky, A. R.; Kurz, T.; Zhang, S.; Voronkov, M.; Steel, P. J. Heterocycles 2001, 55, 1703-1710.
157. (b) Savrda, J.; Ziane, N.; Guihem, J.; Wakselman, M. J. Chem. Res. 1991, 2, 36-37.
158. Ortholand, J.-Y.; Slawin, A. M. Z.; Spencer, N.; Stoddart, J. F.; Williams, D. J. Angew. Chem., Int. Ed. Engl. 1989, 28, 1394-1395.
159. (a) Hamilton, D. G.; Davies, J. E.; Prodi, L.; Sanders, J. K. M. Chem.-Eur. J. 1998, 4, 608-620.
160. (b) Zhang, Q.; Hamilton, D. G.; Feeder, N.; Teat, S. J.; Goodman, J. M.; Sanders, J. K. M. New J. Chem. 1999, 23, 897-903.
161. Alkyne units have been known to deform readily in strained systems, in extreme cases up to 52° over the four atoms of the X-C≡C-X unit. See, inter alia: (a) Eisler, S.; McDonald, R.; Loppnow, G. R.; Tykwinski, R. R. J. Am. Chem. Soc. 2000, 122, 6917-6928.
162. (b) Gleiter, R.; Merger, R. In Modern Acetylene Chemistry; Stang, P. J., Diederich, F., Eds.; VCH: Weinheim, Germany, 1995; pp 285-319.
163. (c) De Graaff, R. A. G.; Gorter, S.; Romers, C.; Wong, H. N. C.; Sondheimer, F. J. Chem. Soc., Perkin Trans. 2 1981, 478-480.
164. (d) Dosa, P. I.; Whitener, G. D.; Vollhardt, K. P. C.; Bond, A. D.; Teat, S. J. Org. Lett. 2002, 4, 2075-2078.
165. Bunz, U. H. F.; Enkelmann, V. Chem.-Eur. J. 1999, 5, 263-266.
166. 4+, DNP, and triazole peaks, consistent with the presence of only one (albeit unsymmetric) species.
167. 4+-based [2]catenanes, see: (a) Vignon, S. A.; Stoddart, J. F. Collect. Czech. Chem. Commun. 2005, 70, 1493-1576.
168. See also: (b) Tseng, H.-R.; Vignon, S. A.; Celestre, P. C.; Stoddart, J. F.; White, A. J. P.; Williams, D. J. Chem.-Eur. J. 2003, 9, 543-556.
169. 4+ ring. We prefer to treat this motion from a different system of reference as the circumrotation of the π-accepting ring around the formally motionless π-donating ring. This semantic distinction emphasizes the geometric equivalence of the above process with the circumrotation of the π-donating ring (rotation 3 in Figure 9). In both processes, one of the rings formally rotates around the axis going through its center, while the other ring remains motionless (and vice versa). Hence, the difference in the spectroscopic consequences of the two processes comes from the difference in the identity of the rotating ring, and not from different modes of rotation. See ref 44a as well as: (a) Ashton, P. R.; Preece, J. A.; Stoddart, J. F.; Tolley, M. S.; White, A. J. P.; Williams, D. J. Synthesis 1994, 1344-1352.
170. 6 cannot be completely dismissed.
171. (a) Oki, M. Applications of Dynamic NMR Spectroscopy to Organic Chemistry; VCH, Weinheim, 1985.
172. (b) Gasparro, F. P.; Kolodny, N. H. J. Chem. Educ. 1977, 54, 258-261.
173. See, inter alia: (a) Hamilton, D. G.; Sanders, J. K. M. Chem. Commun. 1998, 1749.
174. (b) Ashton, P. R. et al. Chem.-Eur. J. 1998, 4, 590-607.
175. (a) Liu, Y. et al. J. Am. Chem. Soc. 2005, 127, 9745-9759.
176. (b) Huang, T. J. et al. Appl. Phys. Lett. 2004, 85, 5391-5393.