Effect of an intramolecular hydrogen bond belt and complexation with the guest on the rotation behavior of phenolic units in pillar[5]arenes

Journal of Physical Chemistry Letters

Volumn 1, Issue 5, 2010, Pages 817-821

  Ogoshi, Tomoki ^a   Kitajima, Keisuke ^a   Aoki, Takamichi ^a   Yamagishi, Tada Aki ^a   Nakamoto, Yoshiaki ^a  

^a KANAZAWA UNIVERSITY   (Japan)

Author keywords

Macromolecules; Soft Matter

Indexed keywords

HOST GUEST COMPLEXES; INTRAMOLECULAR HYDROGEN BOND; NMR MEASUREMENTS; PHENOLIC UNITS; SOFT MATTER; SPLIT PEAK; TIME-SCALES; VIOLOGENS;

ACETONE; COMPLEXATION; HYDROGEN; MACROMOLECULES; NUCLEAR MAGNETIC RESONANCE; PHENOLS; ROTATION; TIME MEASUREMENT;

HYDROGEN BONDS;

EID: 77949396823     PISSN: None     EISSN: 19487185     Source Type: Journal    
DOI: 10.1021/jz900437r     Document Type: Article

References (24)

1. Rekharsky, M. V.; Inoue, Y. Complexation Thermodynamics of Cyclodextrins. Chem. Rev. 1998, 98, 1875-1918.
2. Hishiya, T.; Asanuma, H.; Komiyama, M. Spectroscopic Anatomy of Molecular-Imprinting of Cyclodextrin. Evidence for Preferential Formation of Ordered Cyclodextrin Assemblies. J. Am. Chem. Soc. 2002, 124, 570-575.
3. Harada, A. Cyclodextrin-Based Molecular Machines. Acc. Chem. Res. 2001, 34, 456-464.
4. Harada, A.; Hashidzume, A.; Yamaguchi, H.; Takashima, Y. Polymeric Rotaxanes. Chem. Rev. 2009, 109, 5974-6023.
5. Ogoshi, T.; Takashima, Y.; Yamaguchi, H.;Harada, A. Chemically- Responsive Sol-Gel Transition of Supramolecular Single-Walled Carbon Nanotubes (SWNTs) Hydrogel Made by Hybrids of SWNTs and Cyclodextrins. J. Am. Chem. Soc. 2007, 129, 4878-4879.
6. Ogoshi, T.; Takashima, Y.; Yamaguchi, H.; Harada, A. Cyclodextrin- Grafted Poly(phenylene ethynylene) with Chemically- Responsive Properties. Chem. Commun. 2006, 3702-3704.
7. Miyawaki, A.; Kuad, P.; Takashima, Y.; Yamaguchi, H.; Harada, A. Molecular Puzzle Ring: pseudo[1]Rotaxane from a Flexible Cyclodextrin Derivative. J. Am. Chem. Soc. 2008, 130, 17062-17069.
8. Steiner, T.; Saenger,W. Closure of the Cavity in Permethylated Cyclodextrins through Glucose Inversion, Flipping, and Kinking. Angew. Chem., Int. Ed. 1998, 37, 3404-3407.
9. Mino, R. C.; Susan, A. B.;Welcome, T. M.; Pamela, M. D. New Crystalline Forms of Permethylated β-Cyclodextrin. Chem. Commun. 2004, 2216-2217.
10. Kano, K.; Ishimura, T.; Negi, S. Mechanism for Binding to the Flexible Cavity of Permethylated R-Cyclodextrin. J. Incl. Phenom. Macrocycl. Chem. 1995, 22, 285-298.
11. Kano, K.; Nishiyabu, R.; Asada, T.; Kuroda, Y. Static and Dynamic Behavior of 2:1 Inclusion Complexes of Cyclodextrins and Charged Porphyrins in Aqueous Organic Media. J. Am. Chem. Soc. 2002, 124, 9937-9944.
12. Kano, K.; Nishiyabu, R.; Doi, R. Novel Behavior of O-Methylated β-Cyclodextrins in Inclusion of meso-Tetraarylporphyrins. J. Org. Chem. 2005, 70, 3667-3673.
13. Biros, S. M.; Ullrich, E. C.; Hof, F.; Trembleau, L.; Rebek, J. J. Kinetically Stable Complexes inWater: The Role of Hydration and Hydrophobicity. J. Am. Chem. Soc. 2004, 126, 2870-2876.
14. Guo, D. S.; Wang, L. H.; Liu, Y. Highly Effective Binding of Methyl Viologen Dication and Its Radical Cation by φ-Sulfonatocalix[4,5]arenes. J. Org. Chem. 2007, 72, 7775-7778.
15. The structure of the host-guest complex was investigated by 1HNMRmeasurements. The stoichiometry of the host-guest complex of C8BpyC8 with pillar[5]arene was determined by Job plots and MALDI-TOF mass measurements. Job plots and MALDI-TOF mass measurements confirmed the assumed 1:1 stoichiometry of the inclusion complex. See: Ogoshi, T.; Kanai, S.; Fujinami, S.; Yamagishi, T.; Nakamoto, Y. para- Bridged Pillar[5]arene: Their Lewis Acid Catalyzed Synthesis and Host-Guest Property. J. Am. Chem. Soc. 2008, 130, 5022-5023.
16. Ogoshi, T.; Umeda, K.; Yamagishi, T.; Nakamoto, Y. Through- Space π-Delocalized Pillar[5]arene. Chem. Commun. 2009, 4874-4876.
17. Ogoshi, T.; Kitajima, K.; Yamagishi, T.; Nakamoto, Y. Synthesis and Conformational Characteristics of Nonsymmetric Pillar[5]arene. Org. Lett. 2010, 12, 636-638.
18. Gutsche, C. D. Calixarenes; The Royal Society of Chemistry: Cambridge, U.K., 1989.
19. Calixarenes: A Versatile Class of Macrocyclic Compounds; Vicens, J., Böhmer, V., Eds.; Kluwer Academic: Dordrecht, The Netherlands, 1991.
20. Yamagishi, T.; Moriyama, E.; Konishi, G.; Nakamoto, Y. Syntheses and Cation Extraction Properties of Polycalixarenesfrom φ-Hydroxycalix[6]arene. Macromolecules 2005, 38, 6871-6875.
21. Atwood, J. L.; Dalgarno, S. J.; Hardie, M. J.; Raston, C. L. Selective Single Crystal Complexation of L- or D-Leucine by φ-Sulfonatocalix[6]arene. Chem. Commun. 2005, 337-339.
22. Castro, R.; Godinez, L. A.; Criss, C. M.; Kaifer, A. E. Host Properties of α-Cyclodextrin and a Water-Soluble Calix- [6]arene Probed with Dimeric Bipyridinium Guests. J. Org. Chem. 1997, 62, 4928-4935.
23. Ogoshi, T.; Yamagishi, T.; Nakamoto, Y. Supramolecular Single-Walled Carbon Nanotubes (SWCNTs) Network Polymer Made by Hybrids of SWCNTs and Water-Soluble Calix- [8]arenes. Chem. Commun. 2007, 4776-4778.
24. Araki, K.; Iwamoto, K.; Shinkai, S.; Matsuda, T. pKa″of Calixarenes and Analogs in Nonaqueous Solvents. Bull. Chem. Soc. Jpn. 1990, 63, 3480-3485.