Macromolecules
Article
2010, 39, 17−29. (n) Mayumi, K.; Ito, K. Polymer 2010, 51, 959−967.
(o) Yuen, F.; Tam, K. C. Soft Matter 2010, 6, 4613−4630. (p) Li, J. J.;
Zhao, F.; Li, J. Appl. Microbiol. Biotechnol. 2011, 90, 427−443.
(4) Selected recent publications from >100 per year: (a) Murayama,
H.; Bin Imran, A.; Nagano, S.; Seki, T.; Kidowaki, M.; Ito, K.; Takeoka,
Y. Macromolecules 2008, 41, 1808−1814. (b) Sato, T.; Takata, T.
Macromolecules 2008, 41, 2739−2742. (c) Zhang, W.; Dichtel, W. R.;
Stieg, A. Z.; Benitez, D.; Gimzewski, J. K.; Heath, J. R.; Stoddart, J. F.
Proc. Natl. Acad. Sci. U. S. A. 2008, 105, 6514−6519. (d) Travelet, C.;
Schlatter, G.; Hebraud, P.; Brochon, C.; Lapp, A.; Anokhin, D. V.;
Ivanov, D. A.; Gaillard, C.; Hadziioannou, G. Soft Matter 2008, 4,
1855−1860. (e) Yamashita, A.; Kanda, D.; Katoono, R.; Yui, N.; Ooya,
T.; Maruyama, A.; Akita, H.; Kogure, K.; Harashima, H. J. Controlled
Release 2008, 131, 137−144. (f) Farcas, A.; Jarroux, N.; Guegan, P.;
Fifere, A.; Pinteala, M.; Harabagiu, V. J. Appl. Polym. Sci. 2008, 110,
2384−2392. (g) Koopmans, C.; Ritter, H. Macromolecules 2008, 41,
7418−7422. (h) Terao, J.; Tanaka, Y.; Tsuda, S.; Kambe, N.;
Taniguchi, M.; Kawai, T.; Saeki, A.; Seki, S. J. Am. Chem. Soc. 2009,
131, 18046−18047. (i) Ikeda, T.; Higuchi, M.; Kurth, D. G. J. Am.
Chem. Soc. 2009, 131, 9158−9159. (j) Wang, F.; Zheng, B.; Zhu, K.;
Zhou, Q.; Zhai, C.; Li, S.; Li, N.; Huang, F. Chem. Commun. 2009,
4375−4377. (k) Latini, G.; Winroth, G.; Brovelli, S.; McDonnell, S.
O.; Anderson, H. L.; Mativetsky, J. M.; Samori, P.; Cacialli, F. J. Appl.
Phys. 2010, 107, 124509/1−124509/9. (l) Lee, Y.-G.; Koyama, Y.;
Yonekawa, M.; Takata, T. Macromolecules 2010, 43, 4070−4080.
(m) Isono, T.; Satoh, T.; Kakuchi, T. J. Polym. Sci., Part A: Polym.
Chem. 2011, 49, 3184−3192. (n) Ishiwari, F.; Nakazono, K.; Koyama,
Y.; Takata, T. Chem. Commun. 2011, 47, 11739−11741. (o) Kohsaka,
Y.; Nakazono, K.; Koyama, Y.; Asai, S.; Takata, T. Angew. Chem., Int.
Ed. 2011, 50, 4872−4875.
Gibson, H. W. Macromolecules 1998, 31, 5278−5289. (j) Yamaguchi,
N.; Gibson, H. W. Macromol. Chem. Phys. 2000, 201, 815−824.
(k) Gibson, H. W.; Nagvekar, D. S.; Yamaguchi, N.; Bhattacharjee, S.;
Wang, H.; Vergne, M. J.; Hercules, D. M. Macromolecules 2004, 37,
7514−7529.
(9) (a) Vogtle, F.; Handel, M.; Meier, S.; Ottens-Hildebrandt, S.; Ott,
̈
̈
F.; Schmidt, T. Leibigs Ann. 1995, 739−743. (b) Hubner, G. M.;
̈
Glaser, J.; Seel, C.; Vogtle, F. Angew. Chem., Int. Ed. 1999, 38, 383−
̈
̈
386. (c) Seel, C.; Parham, A. H.; Safarowsky, O.; Hubner, G. M.;
̈
Vogtle, F. J. Org. Chem. 1999, 64, 7236−7242. (d) Reuter, C.;
̈
Wienand, W.; Hubner, G. M.; Seel, C.; Vogtle, F. Chem.Eur. J. 1999,
̈
̈
5, 2692−2697. (e) Reuter, C.; Vogtle, F. Org. Lett. 2000, 2, 593−595.
̈
(10) (a) Hunter, C. A. J. Chem. Soc., Chem. Commun. 1991, 749−751.
(b) Hunter, C. A. J. Am. Chem. Soc. 1992, 114, 5303−5311. (c) Bisson,
A. P.; Carver, F. J.; Eggleston, D. S.; Haltiwanger, R. C.; Hunter, C. A.;
Livingstone, D. L.; McCabe, J. F.; Rotger, C.; Rowan, A. E. J. Am.
Chem. Soc. 2000, 122, 8856−8868.
(11) (a) Muscat, D.; Witte, A.; Kohler, W.; Mullen, K.; Geerts, Y.
̈
̈
Macromol. Rapid Commun. 1997, 18, 233−241. (b) Muscat, D.;
Kohler, W.; Rader, H. J.; Martin, K.; Mullins, S.; Muller, B.; Mullen, K.;
̈
̈
̈
̈
Geerts, Y. Macromolecules 1999, 32, 1737−1745.
(12) For a reviewof polycatenanes,see: Niu, Z.; Gibson, H. W. Chem.
Rev. 2009, 109, 6024−6046.
(13) Mahoney, J. M.; Shukla, R.; Marshall, R. A.; Beatty, A. M.;
Zajicek, J.; Smith, B. D. J. Org. Chem. 2002, 67, 1436−1440.
(14) (a) Gibson, H. W.; Lee, S. H.; Engen, P. T.; Lecavalier, P.; Sze,
J.; Shen, Y. X.; Bheda, M. J. Org. Chem. 1993, 58, 3748−3756. (b) Liu,
S.; Gibson, H. W. Tetrahedron Lett. 1994, 35, 8533−8536. (c) Liu, S.;
Lee, S.-H.; Shen, Y. X.; Gibson, H. W. J. Org. Chem. 1995, 60, 3155−
3162.
(5) (a) Wu, C.; Bheda, M. C.; Lim, C.; Shen, Y. X.; Sze, J.; Gibson,
H. W. Polym. Commun. 1991, 32, 204−207. (b) Shen, Y. X.; Gibson,
H. W. Macromolecules 1992, 25, 2058−2059. (c) Shen, Y. X.; Xie, D.;
Gibson, H. W. J. Am. Chem. Soc. 1994, 116, 537−548. (d) Gibson, H.
W.; Liu, S.; Lecavalier, P.; Wu, C.; Shen, Y. X. J. Am. Chem. Soc. 1995,
117, 852−874. (e) Loveday, D.; Wilkes, G. L.; Bheda, M. C.; Shen, Y.
X.; Gibson, H. W. J. Macromol. Sci., Chem. 1995, A32, 1−27.
(f) Marand, E.; Hu, Q.; Gibson, H. W.; Veytsman, B. Macromolecules
1996, 29, 2555−2562. (g) Gong, C.; Gibson, H. W. Macromolecules
1996, 29, 7029−7033. (h) Gibson, H. W.; Liu, S.; Gong, C.; Joseph, E.
Macromolecules 1997, 30, 3711−3727. (i) Gong, C.; Gibson, H. W.
Angew. Chem., Int. Ed. Engl. 1997, 36, 2331−2333. (j) Gong, C.; Ji, Q.;
Glass, T. E.; Gibson, H. W. Macromolecules 1997, 30, 4807−4813.
(k) Gong, C.; Gibson, H. W. Macromolecules 1997, 30, 8524−8525.
(l) Gong, C.; Gibson, H. W. Macromolecules 1998, 31, 308−313.
(m) Mason, P. E.; Bryant, W. S.; Gibson, H. W. Macromolecules 1998,
32, 1559−1569. (n) Gong, C.; Ji, Q.; Subramaniam, C.; Gibson, H. W.
Macromolecules 1998, 1814−1818.
(15) Crystals were grown from acetone/pentane. A colorless prism
(0.08 × 0.09 × 0.11 mm3) was centered on the goniometer of an
Oxford Diffraction SuperNova diffractometer operating with Cu Kα
radiation. The data collection routine, unit cell refinement, and data
processing were carried out with the program CrysAlisPro
(CrysAlisPro v171.33.31, Oxford Diffraction: Wroclaw, Poland,
2009). The Laue symmetry was consistent with the triclinic space
groups P1 and P-1. The structure was solved in both P-1 and P1 using
SIR92 ( Altomare, A.; Cascarano, G.; Giacovazzo, C.; Guagliardi, A. J.
Appl. Crystallogr. 1993, 26, 343−350 ) (via WinGX: Farrugia, L. J. J.
Appl. Crystallogr. 1999, 32, 837838 ) and the unit cell contents
identified as one rotaxane complex, two acetone molecules, and
additional unidentifiable and disordered solvent. The P-1 solution,
with Z′ = 0.5, forces apparent 50% disorder of the benzyloxy functional
group. The P1 solution showed no disorder in the benzyloxy group,
indicating the true space group is P1 with pseudo-P-1 symmetry. The
structure was refined in P1 using SHELXL-NT (Sheldrick, G. M. Acta
Crystallogr. 2008, A64, 112−122 ). Because of poor data quality (e.g.,
mean I/σ(I) = 0.93 for 0.98−0.94 Å; I > 2σ(I) for 34% reflections to
0.84 Å) and the absence of any heavy atoms, the absolute
configuration could not be determined from the Friedel pairs; the
Friedel opposites were therefore merged. All atoms were refined
isotropically, and a riding model was used for all hydrogen atoms.
Atoms related by pseudoinversion were restrained to have similar 1,2
and 1,3 distances (SAME) and constrained to have identical Uiso values
(EADP) to reduce correlation instability during refinement. The
residual electron density from the unidentifiable disordered solvent
was subtracted out using the SQUEEZE program in PLATON (Spek,
A. L. J. Appl. Crystallogr. 2003, 36, 7−13 ). A total of 109e− was
subtracted from a total void volume of 540 Å3
(6) (a) Gibson, H. W.; Engen, P. New J. Chem. 1993, 17, 723−727.
(b) Nagapudi, K.; Leisen, J.; Beckham, H. W.; Gibson, H. W.
Macromolecules 1999, 32, 3025−3033. (c) Gibson, H. W.; Engen, P.
T.; Lee, S.-H. Polymer 1999, 40, 1823−1832. (d) Gibson, H. W.;
Bryant, W. S.; Lee, S.-H. J. Polym. Sci., Polym. Chem. Ed. 2001, 39,
1978−1993. (e) Zhao, T.; Beckham, H. W.; Gibson, H. W.
Macromolecules 2003, 36, 4833−4837. (f) Lee, M.; Moore, R. B.;
Gibson, H. W. Macromolecules 2011, 44, 5987−5993.
(7) Gibson, H. W.; Bheda, M. C.; Engen, P.; Shen, Y. X.; Sze, J.;
Zhang, H.; Gibson, M. D.; Delaviz, Y.; Lee, S. H.; Wang, L.; Rancourt,
J.; Taylor, L. T. J. Org. Chem. 1994, 59, 2186−2196.
(8) (a) Delaviz, Y.; Gibson, H. W. Macromolecules 1992, 25, 4859−
4862. (b) Gong, C.; Gibson, H. W. J. Am. Chem. Soc. 1997, 119,
5862−5866. (c) Gibson, H. W.; Nagvekar, D.; Powell, J.; Gong, C.;
Bryant, W. Tetrahedron 1997, 53, 15197−15207. (d) Gong, C.;
Gibson, H. W. J. Am. Chem. Soc. 1997, 119, 5862−5866. (e) Gong, C.;
Gibson, H. W. J. Am. Chem. Soc. 1997, 119, 8585−8591. (f) Gibson,
H. W.; Nagvekar, D. S.; Yamaguchi, N.; Wang, F.; Bryant, W. S. J. Org.
Chem. 1997, 62, 4798−4803. (g) Gibson, H. W.; Nagvekar, D. S. Can.
J. Chem. 1997, 75, 1375−1384. (h) Gong, C.; Gibson, H. W. Angew.
Chem., Int. Ed. 1998, 37, 310−314. (i) Gong, C.; Balanda, P. B.;
(16) Yang, J.; Tyberg, C. S.; Gibson, H. W. Macromolecules 1999, 32,
8259−8268.
(17) (a) Liu, S.; Gibson, H. W. Tetrahedron Lett. 1994, 35, 8533−
8536. (b) Liu, S.; Lee, S.-H.; Shen, Y. X.; Gibson, H. W. J. Org. Chem.
1995, 60, 3155−3162.
(18) Anelli, P. L.; Ashton, P. R.; Ballardini, R.; Balzani, V.; Delgado,
M.; Gandolfi, M. T.; Goodnow, T. T.; Kaifer, A. E.; Philp, D. J. Am.
Chem. Soc. 1992, 114, 193−218.
1279
dx.doi.org/10.1021/ma202373x | Macromolecules 2012, 45, 1270−1280