Abstract
This account describes recent examples of multifunctional artificial receptors, which demonstrates our approach to purposive molecular design. The paper is divided into two parts. The first deals with novel crowned spirobenzopyrans as dual-mode signal transducers. The new crowned spirobenzopyrans complement previous crowned spirobenzopyrans from the viewpoint of molecular devices, and a detailed comparison between them is given. The second part is concerned with polypyridine-macrocyclic structures as ribofuranoside receptors. The design of the ribofuranoside receptors was based on the multipoint hydrogen bond complementarity between the receptors and methyl β-(d)-ribofuranoside. The binding affinity of the receptors was very high, so that even native ribose was extracted by them into nonpolar solvents.
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C.J. Pedersen: J. Am. Chem. Soc. 89, 2495 (1967). Idem: ibid. 89, 7017 (1967).
Reviews: Advances in Supramolecular Chemistry (vols. 1–4, Ed. G.W. Gokel), JAI, Greenwich (1990, 1992, 1993, and 1997). F. Vögtle: Supramolecular Chemistry, John Wiley & Sons, Chichester (1991). Frontiers in Supramolecular Organic Chemistry and Photochemistry (Eds. H.-J. Schneider and H. Dürr), VCH, Weinheim (1991). Comprehensive Supramolecular Chemistry (Eds. J.L Atwood, J.E.D. Davies, D.D. MacNicol, and F. Vögtle), Elsevier, Oxford (1996).
Reviews: H.-G. Löhr and F. Vögtle: Acc. Chem. Res. 18, 65 (1985). J.-M. Lehn: Angew. Chem., Int. Ed. Engl. 27, 89 (1988). A. W. Czarnik: Frontiers in Supramolecular Organic Chemistry and Photochemistry (Eds. H.-J. Schneider and H. Dürr), pp. 109–122, VCH,Weinheim (1991). H. Bouas-Laurent, J.-P. Desvergne, F. Fages, and P. Marsau: ibid. pp. 265–286. T. Kaneda: Crown Ethers and Analogous Compounds (Studies in Organic Chemistry vol. 45, Ed. M. Hiraoka), pp. 311–334, Elsevier, Amsterdam (1992). A.W. Czarnik: Advances in Supramolecular Chemistry (vol. 3, Ed. G.W. Gokel), pp. 131–157, JAI, Greenwich (1993). S. Shinkai: Tetrahedron 49, 8933 (1993). Fluorescent Chemosensors for Ion and Molecule Recognition (Ed. A.W. Czarnik), ACS,Washington (1993). J.C. Lockhart: Comprehensive Supramolecular Chemistry (vol. 1, Ed. J.L Atwood, J.E.D. Davies, D.D. MacNicol, and F. Vögtle), pp. 605–634, Elsevier, Oxford (1996). T. Hayashita and M. Takagi: ibid. (vol. 1, Eds. J. L. Atwood, J.E.D. Davies, D.D. MacNicol, and F. Vögtle), pp. 635–669, Elsevier, Oxford (1996). S. Shinkai: ibid. (vol. 1, Eds. J.L. Atwood, J.E.D. Davies, D.D. MacNicol, and F. Vögtle), pp. 671–700, Elsevier, Oxford (1996).
M. Inouye, M. Ueno, T. Kitao, and K. Tsuchiya: J. Am Chem. Soc. 112, 8977 (1990).
M. Inouye: Coord. Chem. Rev. 148, 265 (1996). (b) M. Inouye, T. Miyake, and M. Furusyo: J. Syn. Org. Chem., Jpn. 54, 311 (1996).
M. Inouye, K. Akamatsu, and H. Nakazumi: J. Am. Chem. Soc. 119, 9160 (1997).
Reviews of the chemistry of spiropyrans: R.C. Bertelson: Photochromism (Ed. G.H. Brown), pp. 45–431, Wiley-Interscience, New York (1971). Molecular Models of Photoresponsiveness (Eds. G. Montagnoli and B.F. Erlangered), Plenum, New York (1983). R. Guglielmetti: Photochromism, Molecules and Systems (Studies in Organic Chemistry vol. 40, Eds. H. Dürr and H. Bouas-Laurent), pp. 314–466, Elsevier, Amsterdam (1990).
M. Inouye, M. Ueno, and T. Kitao: J. Org. Chem. 57, 1639 (1992). (b) M. Inouye, M. Ueno, K. Tsuchiya, N. Nakayama, T. Konishi, and T. Kitao: ibid. 57, 5377 (1992). (c) M. Inouye, Y. Noguchi, and K. Isagawa: Angew. Chem., Int. Ed. Engl. 33, 1163 (1994).
Reviews: Molecular Electronic Devices (Eds. F.L. Carter, R.E. Siatkowski, and H. Wohltjen), Elsevier, Amsterdam (1988). Nanotechnology (Eds. B.C. Crandall and J. Lewis), MIT Press, Cambridge (1992). E. Drexler: Nanosystems: Molecular Machinery, Manufacturing and Computation, Wiley, New York (1992).
de Silva et al. reported a fascinating photoionic ‘AND’ gate molecule: A.P. de Silva, H.Q.N. Gunaratne, and C.P. McCoy: Nature 364, 42 (1993). Other dual-mode signal transducers: A.K. Newell and J.H.P. Utley: J. Chem. Soc., Chem. Commun. 800 (1992). T. Saika, T. Iyoda, K. Honda, T. Shimidzu: J. Chem. Soc., Perkin Trans. 2 1181 (1993).
M. Inouye, T. Miyake, M. Furusyo, and H. Nakazumi: J. Am. Chem. Soc. 117, 12416 (1995).
Reviews: J.C. Paulson: Trends Biochem. Sci. 14, 272 (1989). S. Borman: Chem. Eng. News 70, 25 (1992). Idem: ibid. 71, 27 (1993). A. Kobata: Acc. Chem. Res. 26, 319 (1993).
A recent review: Y. Aoyama: Comprehensive Supramolecular Chemistry (vol. 2, Eds. J.L. Atwood, J.E.D. Davies, D.D. MacNicol, and F. Vögtle), pp. 279–307, Elsevier, Oxford (1996).
Representative Examples: Y. Kikuchi, Y. Tanaka, S. Sutarto, K. Kobayashi, H. Toi, and Y. Aoyama: J. Am. Chem. Soc. 114, 10302 (1992). K. Kobayashi, Y. Asakawa, Y. Kato, and Y. Aoyama: ibid. 114, 10307 (1992). Y. Aoyama, Y. Nagai, J. Otsuki, K. Kobayashi, and H. Toi: Angew. Chem., Int. Ed. Engl. 31, 745 (1992). J.M. Coterón, C. Vicent, C. Bosso, and S. Penades: J. Am. Chem. Soc. 115, 10066 (1993). P.B. Savage and S.H. Gellman: ibid. 115, 10448 (1993). G. Das and A.D. Hamilton: ibid. 116, 11139 (1994). T.D. James, K.R.A. Samankumara Sandanayake, and S. Shinkai: Angew. Chem., Int. Ed. Engl. 33, 2207 (1994). G. Deng, T.D. James, and S. Shinkai: J. Am. Chem. Soc. 116, 4567 (1994). J.C. Norrild and H. Eggert: ibid. 117, 1479 (1995).
A.D. Hamilton and D. Van Engen: J. Am. Chem. Soc. 109, 5035 (1987). A.D. Hamilton, N. Pant, and A. Muehldorf: Pure Appl. Chem. 60, 533 (1988). S. Goswami, A.D. Hamilton, and D. Van Engen: J. Am. Chem. Soc. 111, 3425 (1989). T. Tjivikua, G. Deslongchamps, and J. Rebek Jr. ibid. 112, 8408 (1990).
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Inouye, M. ‘Purposive’ Molecular Design for Multifunctional Artificial Receptors. Journal of Inclusion Phenomena 32, 223–233 (1998). https://doi.org/10.1023/A:1008015511415
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DOI: https://doi.org/10.1023/A:1008015511415