Od oddziaływań supramolekularnych do molekularnych

• Autorzy: Brandt K. , Siwy M. , Lach D.

Warianty tytułu

EN

From supramolecular to molecular interactions

• Języki publikacji: PL

Abstrakty

EN

The review is focused on the problems of supramolecular assistance to molecular synthesis which means the employment of supramolecular interactions to control the chemical synthesis, i.e. to guide the regio- and/or stereoselective formation of covalent and/or mechanic bonds. Such an approach results from the tendency to mimic processes occurring in natural biological systems. The special attention is focused on the recent achievements in this field, i.e. on the design of so-called intelligent substrates, which contain in their structure the requisite stereoelectronic information needed to self-assemble spontaneously into a supramolecular intermediate, which converts further into a desired final product after the formation of one or more covalent bonds. Among the unusual structures obtained using this synthetic paradigm, mechanically interlocked molecular compounds, i.e. rotaxanes, catenanes and their supramolecular precursors: psedorotaxanes, are described in more detail, as they display features of bistable chemical switches, and therefore evolve currently a great scientific interest due to their prospective applications in nanotechnologies. Several examples have been given of supramolecular assistance to other complex chemical syntheses, in particular of organic compounds, organo(cyclophosphazenes) and oligonucleotides, enabling to perform them quickly and selectively from polyfunctional reagents, without the necessity to use any protecting groups. It has been emphasized that supramolecular interactions play a special role in guiding so-called self-replication processes of the molecules containing in their structure both reactive groups, able to undergo co-condensation, and complementary to those contained in the substrates supramolecular synthons (motifs), capable to form appropriately oriented ternary complexes with these substrates, in which the functional groups are in favourable position to interact towards the desired product. An influence of spontaneous self-assembly of the substrates, preceding their linking via covalent bond(s), on regio- and stereochemistry of the occurring processes has been discussed, with the special attention being paid to the role of so-called templates (previously named matrices), determining the orientation of the substrates due to the stabilization of particular transition states. Several types of templates have been discussed: complementary hydrogen bonding, metal cations (alkali metal, transition metal), p-donor-p-acceptor interactions and various combinations of the above mentioned; the examples of the respective template-driven syntheses have been quoted. The reactions of functional macrocyclic ligands, assisted by supramolecular interactions with the nucleophilic ion-paired co-reagents, have been only briefly mentioned and limited to the examples of the exchange reactions of benzo-crowns with substituents in aromatic rings, and of chlorocyclophosphazene-crowns.

Słowa kluczowe

PL

chemia supramolekularna; synteza molekularna; templanty; jony metali; synteza templatowa

• Wydawca: Polskie Towarzystwo Chemiczne
• Czasopismo: Wiadomości Chemiczne
• Rocznik: 2000
• Tom: [Z] 54, 5-6
• Strony: 389--434
• Opis fizyczny: schem., rys., bibliogr. 76 poz.

Twórcy

autor

Brandt K.

• Centrum Chemii Polimerów PAN ul. M. Curie-Skłodowskiej 34, 41-800 Zabrze

autor

Siwy M.

• Centrum Chemii Polimerów PAN ul. M. Curie-Skłodowskiej 34, 41-800 Zabrze

autor

Lach D.

• Centrum Chemii Polimerów PAN ul. M. Curie-Skłodowskiej 34, 41-800 Zabrze

• Centrum Chemii Polimerów PAN ul. M.Curie-Skłodowskiej 34, 41-800 Zabrze

Bibliografia

• [1] J.-M. Lehn, Chemia supramolekularna, Instytut Chemii Fizycznej PAN, Warszawa 1993.
• [2] W. Radecka-Paryzek, Przem. Chem., 1997, 76, 299 i literatura tam cytowana.
• [3] J. Lipkowski, Wiad. Chem., Biblioteka, Chemia supramolekularna, Wrocław 1997, s. 5.
• [4] M. Pietraszkiewicz, ibid„ s. 189 i literatura tam cytowana,
• [5] J. S. Lindsey, New J. Chem. 1991, 15, 153 i literatura tam cytowana.
• [6] D. Philp, J.-F. Stoddart, Angew. Chem., Int. Ed. Eng. 1996, 35, 1154 i literatura tam cytowana.
• [7] D. B. Amabilino, J.-F. Stoddart, Chem. Rev. 1995, 95, 2725 i literatura tam cytowana.
• [8] M. C. T. Fyfe, J.-F. Stoddart, Acc. Chem. Res., 1997.30 (10), 393 i literatura tam cytowana.
• [9] V. Balzani, M. Gomez-Lopez, J.-F. Stoddart, Acc. Chem. Res. 1998, 31 (7), 405.
• [10] J.-M. Lehn, Angew. Chem., Int. Ed. Eng., 1990, 29, 1304.
• [11] S. Langford, L. Perez-Garcia, J.-F. Stoddart, Supramol. Chem. 1995, 6, 11.
• [12] V. Videnova-Adrabinska, Wiad. Chem. 1995, 49, 547 i literatura tam cytowana.
• [13] V. Videnova-Adrabinska, Wiad. Chem., Biblioteka, Chemia supramolekularna, Wrocław 1997, s. 41.
• [14] J. Rebek, Science, 1987, 325, 1478.
• [15] P. R. Ashton, M. C. T. Fyfe, S. K. Hickingbottom , S. Menzer, J. F. Fraser Stoddart, A. J. P. White, D. J. Williams, Chem. Eur. J. 1998, 4, 577.
• [16] K. Ariga, T. Kunitake, Acc. Chem. Res., 1998, 31, 371 i literatura tam cytowana.
• [17] R. Hoss, F. Vogtle, Angew. Chem., Int. Ed. Eng. 1994, 33, 375 i literatura tam cytowana.
• [18] A. Terfort, G. Kiedrowski, Angew. Chem., Int. Ed., Eng., 1992, 31, 654.
• [19] D. Sievers, G. Kiedrowski, Chem. Eur. J., 1998, 4, 629 i literatura tam cytowana.
• [20] B. G. Bag, G. Kiedrowski, Pure Appl. Chem., 1996, 68, 2145.
• [21] E. A. Winter, M. M. Conn, J. Rebek, Acc. Chem. Res. 1994, 27, 198.
• [22] L. E. Orgel, Acc. Chem. Res. 1995, 28, 109.
• [23] A. Henbest, R. A. Wilson, J. Chem. Soc., 1957, 1958.
• [24] M. W. Gobel, J. W. Bats, D. Diirner, Angew. Chem. [nt., Ed. Eng., 1992, 31, 207.
• [25] A. V. Bordunov, N. G. Lukyanenko, V. N. Pastushok , K. E. Krakowiak , J. S. Bradshaw, N. K. Dalley, J. Org. Chem. 1995, 60, 4912.
• [26] W.-L. Cheng, Y.-J. Shaw, S. M. Yeh, P. P. Kanakamma, Y.-H. Chen, Ch. Chen, J.-Ch. Shieu, S.-J. Yiin, G.-H. Lee, Y. Wang, T.-Y. Luh, ibid., 1999, 64, 532 i literatura tam cytowana.
• [27] J. Wuckelt, M. Doring, P. Langer, R. Beckert, H. Gorls, ibid., 1999, 64, 365.
• [28] R- G. Brisbois, L. E. Fogel O.-J.-C. Nicaise, P. J. De Weerd, ibid., 1997, 62, 6708.
• [29] Ch. W. A llen, Chem. Rev., 1991, 91, 119.
• [30] J.-P- Harris, K. B. Williams, Inorg. Chem. 1984, 23, 1495.
• [31] F. Sournies, J.-F. Labarre, J. P. Harris, K. B. W illiam s, Inorg. Chim. Acta 1984 90 L61.
• [32] P. C astera, J.-P. Faucher, M. G raffeuil, J.-F. Labarre, J. Mol. Struct. 1988, 176, 295.
• [33] A. El Bakili, P. Castera, J.-P. Faucher, F. Sournies, J.-F. Labarre ibid., 1989,195,21.
• [34] F. Sournies, A. El Bakili, J.-F. Labarre, ibid., 1989, 196, 201.
• [35] P. Castera, J.-P. Faucher, M. Graffeuil, J. F. Labarre, ibid., 1988, 176, 295.
• [36] F. Sournies, L. Labrousse, M. Graffeuil, F. Crasnier, J.-P. Faucher, M.-Ch. Labarre, J.-F. Labarre, Phosphorus, Sulfur and Silicon 1994, 89, 47.
• [37] K. Brandt, I. Porwolik, M. Siwy, T. Kupka, R. A. Shaw, D. B. Davies, M. B. H ursthouse, G. D. Sykara, J. Am. Chem. Soc., 1997, 119, 1143.
• [38] K. Brandt, I. Porwolik, M. Siwy, T. Kupka, R. A. Shaw, S. Ture, A. Clayton, B. Davies, M. B. Hursthouse, G. D. Sykara, J. Org. Chem. 1999, 64, 7299.
• [39] K. Brandt, T. Kupka, J. Drozd, J. C. van de Grampel, A. M eetsm a, A. P. Jekel, Inorg. Chim. Acta, 1995, 228 (2), 187.
• [40] K. Brandt, I. Porwolik, T. Kupka, A. Olejnik, R. A. Shaw, D. B. Davies, J. Org. Chem. 1995, 60, 7433.
• [41] K. Brandt, I. Porwolik , A. Olejnik, R. A. Shaw, D. B. Davies, M. B. Hursthouse, G. D. Sykara, J. Am. Chem. Soc., 1996, 118, 4496.
• [42] J. Brandt, I. Porwolik , M. Siwy, T. Kupka, R. A. Shaw, D. B. Davies, M. B. Hursthouse, G. D. Sykara, ibid., 1997, 119, 12432.
• [43] K. Brandt, 1. Porwolik, M. Siwy, Wiad. Chem., Biblioteka, Chemia supramolekulama, Wrocław 1997, s. 91 i literatura tam cytowana.
• [44] P. Kafarski, B. Lejczak, Chemia bioorganiczna, PWN, Warszawa 1994, s. 226.
• [45] M. Komiyama, Prog. Polym. Sri., 1993, Vol. 18, 871 i literatura tam cytowana.
• [46] F. M. Raym o, J.-F. Stoddart, Xth International Symposium on Molecular Recognition and Inclusion, 20 25.06.1998, Warsaw, Poland, Collected Abstracts, L-14.
• [47] R. E. Gillard , F. M. Raymo, J.-F. Stoddart, Chem. Eur. J. 1997, 3, 1933.
• [48] S. A. Nepogodiev , J.-F. Stoddart, Chem. Rev., 1998, 98, 1959.
• [49] G. M. Whitesides, J. P. Mathias, Ch. T. Seto, Science, 1991, 254, 1312.
• [50] K. C. Russel, J.-M. Lehn, N. Kuritsakas, J. Fischer, New J. Chem., 1998, 123.
• [51] J. C. MacDonald , G. M. Whitesides, Chem. Rev., 1994, 94, 2383.
• [52] J.-M. Lehn, M. Mascal, A. De Cian, J. J. Fischer, Chem. Soc., Chem. Commun 1995, 805.
• [53] N. Kimizuka, T. Kawasaki, K. Hirata, T. Kunitake, J. Am. Chem. Soc., 1995, 117, 6360.
• [54] Przykładowe prace: a) K. Brandt, Z. Jedliński, J. Org. Chem., 1980, 45 (9), 1672; b) K. Brandt, ibid., 1981, 46, 1918, c) K. Brandt, A. P. Jekel, A. Meetsm a, J. C. van dc Grampel, Inorg. Chim. Acta, 1989, 157, 251; d) J. Drozd, K. Brandt, T. Kupka, ibid., 1994, 33, 3602.
• [55] P. Castera, J.-P. Faucher, M. Granier, J.-F. Labarre, Phosphorus, Sulfur, 1987,32, 367 i literatura tam cytowana.
• [56] C. Gong, H. W. Gibson, Angew. Chem., Int. Ed. Eng., 1998, 37 (3), 310 i literatura tam cytowana.
• [57] C. Gong, P. Balanda, H. W. Gibson, Macromolecules, 1998, 31, 5278.
• [58] H. W. Gibson , C. Gong, S. Liu, D. Nagvekar, Macromol. Symp. 1998, 128, 89.
• [59] D. Landini, A. Maia, M. Penso, Comprehensive Supramolecular Chemistry, Pergamon, Elsevier Science 1996, Vol. 1, s. 417.
• [60] R. Cacciapaglia, L. Mandolini, Chem. Soc. Revs., 1993, 221 i literatura tam cytowana.
• [61] K. Brandt, M. Siwy, D. Lach, J. Silberring, w przygotowaniu do druku.
• [62] R. Cacciapaglia, A. R. van Doom , L. Mandolini, D. N. Reinhoudt, W. Verboom, J. Am. Chem. Soc., 1992, 114, 2611.
• [63] G. Schroeder, B. Łęska, B. Gierczyk, ACH Models in Chemistry, 1994, 131.
• [64] G. Schroeder, B. Łęska, Supramol. Chem. 1998, 9, 17.
• [65] U. Koert, M.-M. Harding, J.-M. Lehn, Nature, 1990, 346, 339.
• [66] Np.: a) C. Piguet, G. Berdardinelli, G. H opfgartner, Chem. Rev., 1997, 97 (6), 2005; b) M. J. Hannon, C. P ainting, A. Jacson, J. H am blin, W. E rrington, Chem. Comm., 1997, 1808; c) E. J. Enemark, T. D. Stack, Angew. Chem., Int. Ed. Eng. 1998, 37 (7), 932; d) O. Mamula, A. Vonzelevsky, G. Bernardinelli, ibid., 1998, 37 (3), 290.
• [67] S. White, J. W. Szewczyk, J. M. Turner, E. E. Baird, P. B. Dervan, Nature, 1998, 391 (6666), 468.
• [68] M. Bühner, W. Geuder, W.-K. Kries, S. Hünig, M. Koch, T. Poil, Angew. Chem., Int. Ed. Eng., 1988, 27, 1553.
• [69] M. Anelli, P. R. Asukawa, R. A. Aston, G. Bissell, R. Clavier, A. E. Górski, S. L. Kaifer, G. Langford, G. Mattersteig, S. Menzer, D. Philip , A. M. Z. Slavin, N. Spencer, J.-F. Stoddart, M. S. Tolley, D. J. William s, Chem. Eur. J., 1997, 7. 1113.
• [70] P. T. G link, J.-F. Stoddart, Pure&Appl. Chem., 1998, 70, 419.
• [71] D. B. Amabilino, C. O. Dietrich-Buchecker, A. Livoreil, L. Pérez-Garcia, J.-P. Sauvage, J.-F. Stoddart, J. Am. Chem. Soc., 1996, 118, 3905.
• [72] S. Menzer, A. J. P. White, D. J. Williams, M. Belohradskÿ, Ch. Hamers, F. M. Raymo, A. N. Shipway, J.-F. Stoddart, Macromolecules, 1998, 31, 295.
• [73] T. R. Kelly, C. Zhao, G. J. Bridger, J. Am. Chem. Soc., 1989, 111, 3744.
• [74] J. S. Nowick, Q. Feng, T. Tjivikua, P. Ballester, J. Rebek, ibid., 1991, 113, 8831.
• [75] J.-I. Hong, Q. Feng, V. Rotello, J. Rebek, Science, 1992, 255, 848.
• [76] Q. Feng, T. K. Park, J. Rebek, ibid., 1992, 256, 1179.

Uwagi

PL

Opracowanie rekordu ze środków MEiN, umowa nr SONP/SP/546092/2022 w ramach programu "Społeczna odpowiedzialność nauki" - moduł: Popularyzacja nauki i promocja sportu (2022-2023).