Colorimetric recognition using functional phenolphthalein derivatives

Journal of Inclusion Phenomena and Macrocyclic Chemistry

Volumn 61, Issue 3-4, 2008, Pages 217-225

  Tsubaki, Kazunori ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

Colorimetric recognition; Host guest chemistry; Hydrogen bonding; Molecular recognition; Phenolphthalein; Protic solvent

Indexed keywords

EID: 46649085027     PISSN: 09230750     EISSN: None     Source Type: Journal    
DOI: 10.1007/s10847-008-9419-3     Document Type: Review

References (37)

1. de Silva, A.P., Gunaratne, H.Q.N., Gunnlaugsson, T,. Huxley, A.J.M., McCoy, C.P., Rademacher, J.T., Rice, T.E.: Signaling recognition events with fluorescent sensors and switches. Chem. Rev. 97, 1515-1566 (1997)
2. McQuade, D.T., Pullen, A.E., Swager, T.M.: Conjugated polymer-based chemical sensors. Chem. Rev. 100, 2537-2574 (2000)
3. Wiskur, S.L., Ait-Haddou, H., Lavigne, J.L., Anslyn, E.V.: Teaching old indicators new tricks. Acc. Chem. Res. 34, 963-972 (2001)
4. Kuwabara, T.: Color change indicator for molecules. J. Jpn. Soc. Colour Mater. 78, 265-271 (2005)
5. Nguyen, B.T., Anslyn, E.V.: Indicator-displacement assays. Coord. Chem. Rev. 250, 3118-3127 (2006)
6. Bubnis, B.P., Pacey, G.E.: Alkali metal ion complexation with lariat ethers possessing a chromogenic group. Talanta 31, 1149-1152 (1984)
7. Nakamura, H., Takagi, M., Ueno, K.: Complexation and extraction of alkali metal ions by 4′-picrylaminobenzo-18-crown-6 derivatives. Anal. Chem. 52, 1668-1671 (1980)
8. Bubnis, B.P., Steger, J.L., Wu, Y.P., Meyers, L.A., Pacey, G.E.: Substituent effects on complexation and extraction of alkali metals with chromogenic crown ethers. Anal. Chim. Acta. 139, 307-313 (1982)
9. Fuji, K., Tsubaki, K., Tanaka, K., Hayashi, N., Otsubo, T., Kinoshita, T.: Visualization of molecular length of α,ω-diamines and temperature by a receptor based on phenolphthalein and crown ether. J. Am. Chem. Soc. 121, 3807-3808 (1999)
10. Tsubaki, K., Hayashi, N., Nuruzzaman, M., Kusumoto, T., Fuji, K.: Visual recognition of triamines by phenolphthalein derivatives: consideration of the structure of the colored complex. Org. Lett. 3, 4067-4069 (2001)
11. Tsubaki, K., Nuruzzaman, M., Kusumoto, T., Hayashi, N., Wang, B.-G., Fuji, K.: Visual enantiomeric recognition using chiral phenolphthalein derivatives. Org. Lett. 3, 4071-4073 (2001)
12. Tsubaki, K., Kusumoto, T., Hayashi, N., Nuruzzaman, M., Fuji, K.: Sequence-selective visual recognition of nonprotected dipeptides. Org. Lett. 4, 2313-2316 (2002)
13. Tsubaki, K., Tanima, D., Nuruzzaman, M., Kusumoto, T., Fuji, K., Kawabata, T.: Visual enantiomeric recognition of amino acid derivatives in protic solvents. J. Org. Chem. 70, 4609-4616 (2005)
14. Tsubaki, K., Tanima, D., Kuroda, Y., Fuji, K., Kawabata, T.: Bidirectional and colorimetric recognition of sodium and potassium ions. Org. Lett. 8, 5797-5800 (2006)
15. Tsubaki, K., Tanima, D., Sasamori, T., Tokitoh, N., Kawabata, T.: Colorimetric recognition of the length of α,ω-diamines in water. Tetrahedron Lett. 48, 2135-2138 (2007)
16. Tsubaki, K., Tanima, D., Imamura, Y., Kawabata, T. (submitted)
17. Tamura, Z., Abe, S., Ito, K., Maeda, M.: Spectrophotometric analysis of the relationship between dissociation and coloration, and of the structural formulas of phenolphthalein in aqueous solution. Anal. Sci. 12, 927-930 (1996)
18. Taguchi, K.: Transient binding of phenolphthalein-β-cyclodextrin complex: an example of induced geometrical distortion. J. Am. Chem. Soc. 108, 2705-2709 (1986)
19. Kuwabara, T., Takamura, M., Mastushita, A., Ikeda, H., Nakamura, A., Ueno, A., Toda, F.: Phenolphthalein-modified β-cyclodextrin as a molecule-responsive colorless-to-color change indicator. J. Org. Chem. 63, 8729-8735 (1998)
20. For a recent review for temperature effect on the selectivity: Buschmann, H., Scharf, H.-D., Hoffmann, N., Esser, P.: The isoinversion principle. A general selection model in chemistry. Angew. Chem. Int. Ed. Engl. 30, 477-515 (1991)
21. Naemura, K., Tobe, Y., Kaneda, T.: Preparation of chiral and meso-crown ethers incorporating cyclohexane-1,2-diol derivatives as a steric barrier and their complexation with chiral and achiral amines. Coord. Chem. Rev. 148, 199-219 (1996)
22. Kaneda, T., Sugihara, K., Kamiya, H., Misumi, S.: Synthetic macrocyclic ligands. IV. Lithium ion-characteristic coloration of a "crowned" dinitrophenylazophenol. Tetrahedron Lett. 22, 4407-4408 (1981)
23. Kaneda, T., Umeda, S., Ishizaki, Y., Kuo, H.S., Misumi, S., Kai, Y., Kanehisa, N., Kasai, N.: Azophenolic acerands: amine-selective coloration and crystal structure of a piperidinium saltex. J. Am. Chem. Soc. 111, 1881-1883 (1989)
24. Kaneda, T., Hirose, K., Misumi, S.: Chiral azophenolic acerands: color indicators to judge the absolute configuration of chiral amines. J. Am. Chem. Soc. 111, 742-743 (1989)
25. Naemura, K., Ueno, K., Takeuchi, S., Tobe, Y., Kaneda, T., Sakata, Y.: Azophenolic acerands having chiral 1-phenyl-cis-1,2-cyclohexanediol units: a correlation between enantiorecognitive coloration and host-guest complementarity. J. Am. Chem. Soc. 115, 8475-8476 (1993)
26. Hirose, K., Fuji, J., Kamada, K., Tobe, Y., Naemura, K.: Temperature dependent inversion of enantiomer selectivity in the complexation of optically active azophenolic crown ethers containing alkyl substituents as chiral barriers with chiral amines. J. Chem. Soc. Perkin Trans. 2, 1649-1657 (1997)
27. Ogasahara, K., Hirose, K., Tobe, Y., Naemura, K.: Preparation of optically active azophenolic crown ethers containing 1-phenylethane-1,2-diol and 2,4-dimethyl-3-oxapentane-1,5-diol as a chiral subunit: temperature-dependent enantiomer selectivity in the complexation with chiral amines. J. Chem. Soc. Perkin Trans. 1, 3227-3236 (1997)
28. Hirose, K., Ogasahara, K., Nishioka, K., Tobe, Y., Naemura, K.: Enantioselective complexation of phenolic crown ethers with chiral aminoethanol derivatives: effects of substituents of aromatic rings of hosts and guests on complexation. J. Chem. Soc. Perkin Trans. 2, 1984-1993 (2000)
29. Job, P.: Formation and stability of inorganic complexes in solution. Ann. Chim. 9, 113-203 (1928)
30. Rose, N.J., Drago, R.S.: Molecular addition compounds of iodine. I. An absolute method for the spectroscopic determination of equilibrium constants. J. Am. Chem. Soc. 81, 6138-6145 (1959)
31. Hirose, K.J.: Inclusion phenom.: a practical guide for the determination of binding constants. Macrocyclic Chem. 39, 193-209 (2001)
32. Still, W.C.: Discovery of sequence-selective peptide binding by synthetic receptors using encoded combinatorial libraries. Acc. Chem. Res. 29, 155-163 (1996)
33. Hossain, M.A., Schneider, H.-J.: Sequence-selective evaluation of peptide side-chain interaction. New artificial receptors for selective recognition in water. J. Am. Chem. Soc. 120, 11208-11209 (1998)
34. Tashiro, S., Tominaga, M., Kawano, M., Therrien, B., Ozeki, T., Fujita, M.: Sequence-selective recognition of peptides within the single binding pocket of a self-assembled coordination cage. J. Am. Chem. Soc. 127, 4546-4547 (2005)
35. Wehner, M., Janssen, D., Schaefer, G., Schrader, T.: Sequence-selective peptide recognition with designed modules. Eur. J. Org. Chem. 138-153 (2005)
36. Bush, M.E., Bouley, N.D., Urbach, A.R.: Charge-mediated recognition of N-terminal tryptophan in aqueous solution by a synthetic host. J. Am. Chem. Soc. 127, 14511-14517 (2005)
37. Israelachvili, J.N.: Intermolecular and Surface Forces. Academic Press, London (1992)