RESEARCH ARTICLE
Free to Read
Steric effects on complexation of bis(meta-phenylene)-32-crown-10 derivatives with paraquats
Zhenbin Niu,
Feihe Huang,
Harry W. Gibson,
Zhenbin Niu
Department of Chemistry, Virginia Polytechnic Institute and State University, Blacksburg, VA, USA
Search for more papers by this authorFeihe Huang
Department of Chemistry, Virginia Polytechnic Institute and State University, Blacksburg, VA, USA
Search for more papers by this authorCorresponding Author
Harry W. Gibson
Department of Chemistry, Virginia Polytechnic Institute and State University, Blacksburg, VA, USA
Correspondence
Harry W. Gibson, Department of Chemistry, Virginia Polytechnic Institute and State University, Blacksburg, VA, USA
Email: [email protected]
Search for more papers by this authorZhenbin Niu,
Feihe Huang,
Harry W. Gibson,
Zhenbin Niu
Department of Chemistry, Virginia Polytechnic Institute and State University, Blacksburg, VA, USA
Search for more papers by this authorFeihe Huang
Department of Chemistry, Virginia Polytechnic Institute and State University, Blacksburg, VA, USA
Search for more papers by this authorCorresponding Author
Harry W. Gibson
Department of Chemistry, Virginia Polytechnic Institute and State University, Blacksburg, VA, USA
Correspondence
Harry W. Gibson, Department of Chemistry, Virginia Polytechnic Institute and State University, Blacksburg, VA, USA
Email: [email protected]
Search for more papers by this authorContract grant sponsor: National Science Foundation.
Contract grant number: DMR0704076.
Contract grant sponsor: American Chemical Society.
Contract grant number: 47644-AC.
Abstract
Novel 5,5′-disubstituted BMP32C10 derivatives bearing different sized substituents were designed and prepared. The stoichiometries and complexation behavior between these hosts and paraquats were studied. It was found that bulky 5,5′-substituents disfavor complexation with paraquats by hindering the formation of [2]pseudorotaxane and “taco” complexes.
References
- 1 a)C. J. Pedersen, J. Am. Chem. Soc. 1967, 89, 2495;
- b)C. J. Pedersen, J. Am. Chem. Soc. 1967, 89, 7017;
- c)C. J. Pedersen, J. Org. Chem. 1971, 36, 254.
- 2 a)A. Manjula, M. Nagarajan, Arkivoc 2001, 8, 165;
10.3998/ark.5550190.0002.818 Google Scholar
- b)Y. X. Shen, P. T. Engen, M. A. G. Berg, J. S. Merola, H. W. Gibson, Macromolecules 1992, 25, 2786.
- 3 a)For reviews see: F. Huang, H. W. Gibson, Progr. Polym. Sci. 2005, 30, 982;
- b)Z. Niu, H. W. Gibson, Chem. Rev. 2009, 109, 6024;
- c)D. Thibeault, J.-F. Morin, Molecules 2010, 15, 3709;
- d)M. Arunachalam, H. W. Gibson, Progr. Polym. Sci. 2014, 39, 1043;
- e)W. R. Dichtel, O. S. Miljanic, W. Zhang, J. M. Spruell, K. Patel, I. Aprahamian, J. R. Heath, J. F. Stoddart, Acc. Chem. Res. 2008, 41, 1750;
- f)M. Xue, Y. Yang, X. Chi, Z. Zhang, F. Huang, Acc. Chem. Res. 2012, 45, 1294;
- g)M. Deska, J. Kozlowska, W. Sliwa, Arkivoc 2013, 1, 66;
- h)M. Zhang, X. Yan, F. Huang, Z. Niu, H. W. Gibson, Acc. Chem. Res. 2014, 47, 1995;
- i)Y. Han, Y. Jiang, C.-F. Chen, Tetrahedron 2015, 71, 503.
- 4 a)Some recent publications: H. W. Gibson, A. Farcas, J. W. Jones, Z. Ge, F. Huang, M. Vergne, D. M. Hercules, J. Polym. Sci. Polym. Chem. Ed. 2009, 47, 3518;
- b)S. Li, M. Liu, B. Zheng, K. Zhu, F. Wang, N. Li, X.-L. Zhao, F. Huang, Org. Lett. 2009, 11, 3350;
- c)M. Lee, D. Schoonover, A. Gies, D. M. Hercules, H. W. Gibson, Macromolecules 2009, 42, 6483;
- d)M. Zhang, Y. Luo, B. Zheng, X. Yan, F. R. Fronczek, F. Huang, Eur. J. Org. Chem. 2010, 35, 6798;
- e)M. Lee, R. B. Moore, H. W. Gibson, Macromolecules 2011, 44, 5987;
- f)S.-L. Li, T. Xiao, B. Hu, Y. Zhang, F. Zhao, Y. Ji, Y. Yu, C. Lin, L. Wang, Chem. Commun. 2011, 47, 10755;
- g)H. W. Gibson, Y. X. Shen, M. C. Bheda, C. Gong, Polymer 2014, 55, 3202;
- h)Y. Ye, S.-P. Wang, B. Zhu, T. R. Cook, J. Wu, S. Li, P. J. Stang, Org. Lett. 2015, 17, 2804;
- i)S. Bhattacharjaee, C. Gong, J. W. Jones, H. W. Gibson, Polymer 2015, 81, 99;
- j)M. Lee, H. W. Gibson, J. Polym. Sci., Part A, Polym. Chem. 2016, 54, 1647;
- k)I. R. Fernando, M. Frasconi, Y. Wu, W.-G. Liu, M. R. Wasielewski, W. A. Goddard, J. F. Stoddart, J. Am. Chem. Soc. 2016, 138, 10214.
- 5 a)W. S. Bryant, I. Guzei, A. L. Rheingold, H. W. Gibson, Org. Lett. 1999, 1, 47;
- b)J. W. Jones, L. N. Zakharov, A. L. Rheingold, H. W. Gibson, J. Am. Chem. Soc. 2002, 124, 13378;
- c)F. Huang, F. R. Fronczek, H. W. Gibson, Chem. Commun. 2003, 1480;
- d)F. Huang, J. W. Jones, C. Slebodnick, H. W. Gibson, J. Am. Chem. Soc. 2003, 125, 14458;
- e)F. Huang, L. N. Zakharov, W. Bryant, A. L. Rheingold, H. W. Gibson, Chem. Commun. 2005, 3268;
- f)F. Huang, P. Gantzel, D. S. Nagvekar, A. L. Rheingold, H. W. Gibson, Tetrahedron Lett. 2006, 47, 7841;
- g)S. Li, M. Liu, B. Zheng, K. Zhu, F. Wang, N. Li, X.-L. Zhao, F. Huang, Org. Lett. 2009, 11, 3350
- 6 a)Folding of the 5-hydroxymethyl derivative of BMP32C10 to complex g1 was favored by H-bonding of the hydroxyl oxygen with the β-protons (Hp2) of the guest: F. Huang, L. N. Zakharov, W. S. Bryant, A. L.; Rheingold, H. W.; Gibson, Chem. Commun. 2005, 3268-3270
- b)Pseudocryptand formation via chelation of 5,5’-hydroxy moieties of BMP32C10 with trifluoroacetate anions resulted in greatly enhanced complexation because of the enforced folding: F. Huang, J. W. Jones, H. W. Gibson, Chem. Commun. 2005, 1693
- c)Pseudocryptand-type pseudorotaxanes were later isolated and characterized by X-ray crystallography from 5,5’-diesters of BMP32C10 diol (1b) derived from 2-picolinic acid, quinaldic acid and naphthyridine-2-carboxylic acid, aided by π–stacking of the aromatic substituents: Z. Niu, C. Slebodnick, D. V. Schoonover, H. Azurmendi, K. Harich, H. W. Gibson, Org. Lett. 2011, 13, 2872;
- d)A rotaxane was prepared in 6% yield based on BMP32C10 and a paraquat derivative: S. Li, K. Zhu, B. Zheng, X. Wen, N. Li, F. Huang, Eur. J. Org. Chem. 2009, 7, 1053;
- e)A [2]catenane was prepared based on cyclobis(paraquat-p-phenylene) and BMP32C10 in 17% yield using an extended paraquat with a monoquaternized 4,4′-bipyridine moiety: J. F. Stoddart, D. J. Williams, D. B. Amabilino, P.-L. Anelli, P. R. Ashton, G. R. Brown, E. Cordova, L. A. Godinez, W. Hayes, J. Am. Chem. Soc. 1995, 117, 11142;
- f)Dicarbazyl derivative 1f yielded both pseudorotaxane and taco-type single crystals by varying the host-guest ratio in the solution: Z. Niu, C. Slebodnick, K. Bonrad, F. Huang, H. W. Gibson, Org. Lett. 2011, 13, 3992.
- 7 a)H. W. Gibson, D. S. Nagvekar, Can. J. Chem. 1997, 75, 1375;
- b)H. W. Gibson, D. S. Nagvekar, N. Yamaguchi, F. Wang, W. S. Bryant, J. Org. Chem. 1997, 62, 4798.
- 8V. Percec, C.-H. Ahn, T. K. Bera, G. Ungar, D. J. P. Yeardley, Chem. Eur. J. 1999, 5, 1070.
10.1002/(SICI)1521-3765(19990301)5:3<1070::AID-CHEM1070>3.0.CO;2-9 CAS Web of Science® Google Scholar
- 9V. A. Koshchii, Y. B. Kozlikovskii, A. A. Matyusha, Zh. Org. Khim. 1988, 24, 1508.
