PL EN


Preferencje help
Widoczny [Schowaj] Abstrakt
Liczba wyników
Tytuł artykułu

Pochodne porfiryn zawierające fragment acetylenowy

Identyfikatory
Warianty tytułu
EN
Porphyrin derivatives with an acetylene moiety
Języki publikacji
PL
Abstrakty
EN
The monograph gives a review of literature on porphyrinoids containing an ace-tylene unit attached at macrocyclic perimeter or built into a coordination core. The inclusion of an acetylene fragment provides an unusual structural motif because of its symmetrical cylindrical structure, coordination ability towards metal ions and reactivity. The synthesis, coordination properties and reactivity of porphyrin analogs with an ethynylene unit embedded in the macrocyclic skeleton have been described. Most of such macrocycles belong to stretched porphycenes and heteroporphycenes [8, 9]. The distinct class of expanded porphyrin analogs is delivered by very stable cyclooligothiophenediacetylenes with different size of the interior cavity [16]. A novel type of contracted heteroporphyrins namely dithiaethyneporphyrins, with an acetylene moiety introduced instead of one of pyrrole units, has been also characterized [17, 18]. These macrocycles display unique features of an [18]triphyrin(4.1.1) frame. The introduction of an alkyne moiety outside porphyrinic macrocycle yields meso- or B-alkynylporphyrins [38-42, 71-75]. The synthetic pathways and spectroscopic properties of alkynylporphyrins are included in the second part of the presented review. These macrocycles are widely used as building blocks in the construction of conjugated oligomeric and polymeric porphyrins and metalloporphyrins [81-85, 89-93]. Moreover, the paper provides classification of such ? conjugated systems, which are extensively explored in the analysis of charge or electron density transfer due to the strong electronic conjugation of acetylene with the [pi] system of the porphyrin ring.
Rocznik
Strony
339--371
Opis fizyczny
bibliogr. 118 poz., wykr.
Twórcy
autor
  • Zakład Chemii Porfiryn i Metaloporfiryn, Wydział Chemii Uniwersytet Wrocławski, ul. F. Joliot-Curie 14, 50-383 Wrocław
Bibliografia
  • [1] Bioinorganic Chemistry, I. Bertini, H.B. Gray, S. Lippard, J.S. Valentine, Eds., University Science Books: Mill Valley, California, USA, 1994.
  • [2] Principles of Bioinorganic Chemistry, S. Lippard. J.M. Berg, Eds., University Science Books: Mill Valley, California, USA, 1994.
  • [3] A.R. Battersby, E. McDonald, Biosynthesis of Porplryrins, Chlorins, andCorrhts, [w:] Porphyrins andMetalloporphyrins, K.M. Smith, Ed., Elsevier; Amsterdam, 1975; pp. 61-122.
  • [4] J.-H. Chou, H. Singh Nalwa, M.E. Kosal, N.A. Raków, K.S. Suslick, Applications of Porphyrins andMetalloporphyrins to Materials Chemistry, [w:] The Porphyrin Handbook, K.M. Kadish, K.M. Smith, R. Guilard, Eds., Academic Press: San Diego, CA, 2000, Tom 6, Rozdział 41,.pp. 43-131.
  • [5] T. Malinski, Porphyrin-Based Electrochemical Sensors, [w:] The Porphyrin Handbook. K.M. Kadish, K.M. Smith, R. Guilard, Eds., Academic Press: San Diego. CA, 2000, Tom 6, Rozdział 44, pp. 231-256.
  • [6] R.K. Pandey, G. Zheng. Porphyrins as Photosensitizers in Photodynamic Therapy, [w] The Porphyrin Handbook, K.M. Kadish, K.M. Smith, R. Guilard, Eds. Academic Press: San Diego, CA, 2000, Tom 6, Rozdział 43, pp. 157-230.
  • [7] T. Aida, S. Inoue, Metalloporphyrim as Catalysts for Precision Macromolecular Synthesis, [w:] The Porphvrin Handbook, K.M. Kadish, KM. Smith, R. Guilard, Eds., Academic Press: San Diego, CA, 2000, Tom 6, Rozdział 42, pp. 133-156.
  • [8] J.L. Sessler, S.J. Weghorn, Expanded, Contracted& IsomericPorphyrins, [w:] Tetraliedron Organic Chemistry Series, J.E. Baldwin, P.D. Magnus, Eds., Elsevier Science Ltd., Oxford, U.K., 1997.
  • [9] J.L. Sessler, A. Gebauer, S.J. Weghorn, Expanded Porphyrins, [w:] The Porphyrin Handbook, K.M. Kadish, K.M. Smith, R. Guilard, Eds., Academic Press: San Diego, CA, 2000, Tom 2, Rozdział 2, pp. 55-124.
  • [10] L. Latos-Grażyński, Core Modified Heteroanalogues of Porpliyrins, [w:] The Porphyrin Handbook, K.M. Kadish, K.M. Smith, R. Guilard, Eds., Academic Press: San Diego, CA, 2000, Tom 2, Rozdział 14, pp. 361-416.
  • [11] PJ. Chmielewski, L. Latos-Grażyński, K. Rachlewicz, T. Głowiak, Angew. Chem. Int. Ed. Engl., 1994, 33, 779.
  • [12] H. Furuta, T. Asano, T. Ogawa, J. Am. Chem. Soc, 1994, 116, 767.
  • [13] T.D. Lash, S.T. Chaney, Angew. Chem. Int. Ed. Engl., 1997, 36, 839.
  • [14] E. Pacholska, L. Latos-Grażyński, Z. Ciunik, Chem. Eur. J., 2002, 8, 5403.
  • [15] J.L. Sessler, D. Seidel, Angew. Chem. Int. Ed., 2003, 42, 5134.
  • [16] J. Kromer, I. Rios-Carreras, G. Fuhrmann, C. Musdi, M. Wunderlin, T. Debaerdemaeker, E. Mena-Osteritz, P. Bauerle, Angew. Chem. Int. Ed. Engl., 2000, 39, 3481.
  • [17] A. Berlicka, L. Latos-Grażyński, T. Lis, Angew. Chem. Int. Ed., 2005, 44, 5288.
  • [18] A. Berlicka, N. Sprutta, L. Latos-Grażyński, Chem. Commun., 2005, 3346.
  • [19] E. Vogel, M. Kocher, H. Schmickler, J. Lex, Angew. Chem. Int. Ed. Engl., 1986, 25, 257.
  • [20] N. Jux, P. Koch, H. Schmickler, J. Lex, E. Vogel, Angew. Chem. Int. Ed. Engl., 1990, 29, 1385.
  • [21] D.O. Martire, N. Jux, P.F. Aramendia, R.M. Negri, J. Lex, S.E. Braslavsky, K. Schaffner, E. Vogel, J. Am. Chem. Soc, 1992, 114, 9969.
  • [22] D.H. Cho, J.H. Lee, B.H. Kim, J. Org. Chem. 1999, 64, 8048.
  • [23] B.A. Trofimov, L.N. Sobenina, A.P. Demenev, A.I. Mikhaleva, Chem. Rev., 2004, 104, 2481.
  • [24] C. Kabuto, Y Kitahara, M. Iyoda, O. Nakagawa, Tetrahedron Lett., 1976, 32, 2787.
  • [25] M. Nakagawa, Angew. Chem. Int. Ed. Engl. 1979, 18, 202.
  • [26] K. Mullen, Chem. Rev. 1984, 84, 603.
  • [27] A. Berman, H. Levanon, E. Vogel, N. Jux, Chem. Phys. Lett., 1993, 211, 549.
  • [28] C. Bernard, J.P. Gisselbrech, M. Gross, N. Jux, E. Vogel, J. Electroanal. Chem. 1995,381, 159.
  • [29] T. Kawase, H.R. Darabi, R. Uchimiya, M. Oda, Chem. Lett., 1995, 499.
  • [30] E. Vogel. N. Jux, J. Dorr, T. Pelster, T. Berg, H.-S. Bóhm, F. Behrens, J. Lex, D. Bremm, G. Hohlneicher, Angcv. Chem. Int. Ed. Engl., 2000, 39, 1101.
  • [31] H. Kurata, H. Baba, M. Oda, Chem. Lett., 1997, 572.
  • [32] S.J. Weghorn, V. Lynch, J.L. Sessler,. Tetrahedron Lett., 1995, 36, 4713.
  • [33] G. Fuhrmann, T. Debaerdemaeker, P. Bauerle, Chem. Comunn., 2003, 948.
  • [34] E. Mena-Osteritz, P. Bauerle, Adv. Mater. 2001, 13, 243.
  • [35] D.P. Arnold. A.W. Johnson, M. Mahendran, J. Chem. Soc, Perkin Trans. 1, 1978, 366.
  • [36] J.S. Lindsey, I.C. Schreiman, H.S. Hsu, P.C. Kearney. A.M. Marguerettaz, J. Org. Chem. 1987 52, 827.
  • [37] J.S. Lindsey. Synthesis of meso-Substituted Porphyrins, [w:] The Porphyrin Handbook, K.M. Kadish, K. M. Smith, R. Guilard, Eds., Academic Press: San Diego, CA, 2000, Tom 1, Rozdział 2, pp. 45-118.
  • [38] H.L. Anderson, Tetrahedron Lett., 1992, 33, 1101.
  • [39] M.J. Plater, S. Aiken, G. Bourhil, Tetrahedron, 2002, 58, 2415
  • [40] H.L. Anderson, A.P. Wylie, K. Prout, K. J. Chem. Soc., Perkin Trans. 1, 1998, 1607
  • [41] L.R. Milgrom, G. Yahioglu, Tetrahedron Lett., 1995, 36, 9060
  • [42] L.R. Milgrom, R.D. Rees, G. Yahioglu, Tetrahedron Lett., 1997, 38, 4905
  • [43] A. Krivokapic, A.R. Cowley, H.L. Anderson, J. Org. Chem., 2003, 68, 1089
  • [44] G. Proess, D. Pankert, L. Hevesi, Tetrahedron Lett., 1992, 33, 269
  • [45] G.S. Wilson, H.L. Anderson, Synlett, 1996, 1039.
  • [46] L.R. Milgrom, G. Yahioglu, Tetrahedron Lett., 1996, 37, 4069
  • [47] S.M. LeCours, CM. Philips, J.C. de Paula, M.J. Therien, J. Am. Chem. Soc., 1997, 119, 12578
  • [48] K.-Y. Tomizaki, A.B. Lysenko, M. Taniguchi. J.S. Lindsey, Tetrahedron, 2004, 60, 2011
  • [49] Z. Liu, A.A. Yasseri, R.S. Loewe, A.B. Lysenko, V.L V. Misra, J.S. Lindsey, D.F. Bocian, J. Org. Chem., 2004, 69, 5568
  • [50] S. Smeets, W. Dehaen. Tetrahedron Lett., 1998, 39, 9841
  • [51] S.G. DiMagno, V.S.-Y. Lin, M.J. Therien, J. Org. Chem., 1993, 58, 5983
  • [52] S. Shanmugathasan, C. Edwards, R.W. Boyle, Tetrahedren, 2000, 56, 1025
  • [53] M.J. Plater, S. Aiken, G. Bourhill, Tetrahedron Lett., 2001, 42, 2225
  • [54] G.A. Baker, F.V. Bright, M.R. Detty, S. Pandey, C.E. Stilts H., Yao J., Porphyrins Phthalocyanines, 2000, 4, 669.
  • [55] J. Rosenthal, E.R. Young, D.G. Nocera, Inorg. Chem., 2007, 46, 8668
  • [56] D.P. Arnold, R.D. Hartnell, Tetrahedron, 2001, 57, 1335.
  • [57] D.P. Arnold, D.A. James, J. Org. Chem., 1997, 62, 3460.
  • [58] N.P. Redmore, I.V. Rubstov, M.J. Therien, J. Am. Chem. Soc, 2003, 125, 8769.
  • [59] H.T. Uyeda, Y. Zhao, K. Wostyn, I. Asselberghs, K. Clays, A. Persoons, M.J. Therien, J. Am. Chem. Soc, 2002, 124, 13806.
  • [60] A. Berlicka, L. Latos-Grażyński, T. Lis, Inorg. Chem., 2005, 44, 4522.
  • [61] M.Nath, J.C. Huffman, J.M. Zaleski, J. Am. Chem. Soc, 2003, 125, 11484.
  • [62] M. Yeung, A.C.H. Ng, M.G.B. Drew, E. Vorpagel, E.M. Breitung, R.J. McMahon, D.K.P. Ng, J. Org. Chem., 1998, 63, 7143.
  • [63] L. Karki, F.W. Vance, J.T. Hupp, S.M. LeCours, M.J. Therien, J. Am. Chem. Soc, 1998,120, 2606.
  • [64] T.G. Zhang, Y. Zhao, I. Asselberghs, A. Persoons, K. Clays, M.J. Therien, J. Am. Chem. Soc, 2005, 127, 9710.
  • [65] S.M. LeCours, S.G. DiMagno, M.J. Therien, J. Am. Chem. Soc, 1996,118, 11854.
  • [66] E. Hindin, C. Kirmaier, JR. Diers, K. Tomizaki, M. Taniguchi, J.S. Lindsey, D.F. Bocian, D. Holten, J. Phys. Chem. B, 2004,108. 8190.
  • [67] H.L. Anderson, Chem. Commun., 1999,2323.
  • [68] V.S.Y. Lin, S.G. DiMagno, M.J. Therien, Science, 1994, 264, 1105.
  • [69] R. Shediac, M.H.B. Gray, H.T. Uyeda, R.C. Johnson, J.T. Hupp, P.J. Angiolillo, M.J. Therien, J. Am. Chem. Soc, 2000, 122, 7017.
  • [70] D.P. Arnold, CA. Heath, D.A. James, New J. Chem., 1998, 1377.
  • [71] H. Aihara, L. Jaquinod, D.J. Nurco, K.M. Smith, Angew. Chem. Int. Ed., 2001, 40, 3439.
  • [72] M. Nath, J.C. Huffman, J.M. Zaleski, Chem. Commun., 2003, 858.
  • [73] T. Chandra, B.J. Kraft, J.C. Huffman, J.M. Zaleski, Inorg. Chem., 2003, 42, 5158.
  • [74] S.A. Vail, D.I. Schuster, D.M. Guldi, M. Isosomppi, N. Tkachenko, H. Lemmetyinen, A. Palkan. L. Echegoyen, X. Chen, J.Z.H. Zhang. J. Phys. Chem. B, 2006, 110, 14155
  • [75] P.J. Angiollilo, V.S.Y. Lin, J.M. Vanderkooi, J.M. Therien, J. Am. Chem. Soc, 1995, 117, 12514.
  • [76] M. Nath, J.C. Huffman, J.M. Zaleski, J. Am. Chem. Soc, 2003, 125, 11484
  • [77] H.L. Anderson, S.J. Martin, D.D.C. Bradley, Angew. Chem. Int. Ed. Engl., 1994, 33, 655
  • [78] H.L. Anderson, Inorg. Chem., 1994, 33, 972.
  • [79] M.J. Crossley, P.L. Burn, J. Chem. Soc, Chem. Commun., 1991, 1569.
  • [80] B. Jiang, S. Yang, W.E. Jones Jr., Chem. Mater., 1997, 9, 2031.
  • [81] V.S.Y. Lin, J.M. Therien, Chem. Eur. J., 1995, 1, 645.
  • [82] P.N. Taylor, J. Huuskonen, G. Rumbles, R.T. Aplin, E. Williams, H.L. Anderson, Chem. Commun., 1998, 909.
  • [83] K. Susumu, M.J. Therien, J. Am. Chem. Soc, 2002,124, 8550.
  • [84] R. Shediac, M.H.B. Gray, H.T. Uyeda, R.C. Johnson, J.T. Hupp, P.J. Angiolillo, M.J. Therien, J. Am. Chem. Soc, 2000, 122, 7017.
  • [85] H. Higuchi, T. Maeda, K. Miyabayashi, M. Miyake, K. Yamamoto, Tetrahedron Lett., 2002, 43, 3097.
  • [86] G.S. Wilson, H.L. Anderson, Chem. Commun., 1999, 1539.
  • [87] P.N. Taylor, H.L. Anderson, J. Am. Chem. Soc, 1999,121, 11538.
  • [88] J.T. Fletcher, M.J. Therien, Inorg. Chem:, 2002, 41, 331.
  • [89] J.J. Piet, P.N. Taylor, H.L. Anderson, A. Osuka, J.M. Warman, J. Am. Chem. Soc, 2000,122, 1749.
  • [90] B. Jiang, S. Yang, D.C. Barbini, W.E. Jones Jr., Chem. Commun., 1998, 213.
  • [91] P.N. Taylor, A.P. Wylie. J. Huuskonen, H.L.Anderson, Angew. Chem. Int. Ed. Engl., 1998, 37,986.
  • [92] N. Hayashi, A. Matsuda, E. Chikamatsu, K. Mori, H. Higuchi, Tetrahedron Lett., 2003, 44, 7155.
  • [93] T. Yamamoto, N. Fukushima, N. Hisashi, T. Maruyama, I. Yamaguchi, I. Macromolecules, 2000, 33, 5988.
  • [94] S. Rucareanu, O. Mongin, A. Schuwey, N. Hoyler, A. Gossauer, J. Org. Chem., 2001, 66, 4973.
  • [95] A. Ferri, G. Polzonetti, S. Licoccia, R. Paolesse, D. Favretto, P. Traldi, M.V. Russo, J. Chem. Soc, Dalton Trans., 1998,4063.
  • [96] W.J. Youngblood, D.T. Gryko. R.K. Lammi, D.F. Bocian, D. Holten, J.S. Lindsey, J. Org. Chem., 2002,67,2111.
  • [97] SJ. Yang, J.Seth, J.P. Strachan, S. Gentemann, D.Kim, D. Holten, J.S. Lindsey, D.F. Bocian, J. Porphyrins Phthalocyanines, 1999, 3, 117.
  • [98] D. Holten, D.F. Bocian, J.S. Lindsey. Ace. Chem. Res., 2002, 35, 57.
  • [99] K. Kilsa, J. Kajanus. J. Martensson, B. Albinsson, J. Phys. Chem. B, 1999. 103, 7329.
  • [100] I. Gupta, M. Ravikanth, J. Org. Chem., 2004, 69, 6796.
  • [101] R.W.Wagner, T.E. Johnson, J.S. Lindsey, J. Am. Chem. Soc, 1996, 118, 11166.
  • [102] K. Tomizaki, A.B. Lysenko, M.Taniguchi, J.S. Lindsey, Tetrahedron, 2004, 60, 2011.
  • [103] C. Clausen, D.T. Gryko, R.B. Dabke. N. Dontha, D.F. Bocian, W.G. Kuhr, J.S. Lindsey, J. Org. Chem., 2000, 65, 7363.
  • [104] O. Mongin, A. Gossauer, Tetrahedron, 1997, 53, 6835.
  • [105] D. Kumaresan, N. Agarwal, M. Ravikanth, J. Chem. Soc, Perkin Trans. 1, 2001. 1644.
  • [106] S. Anderson, H.L. Anderson, A. Bashall, M. McPartlin, J.K.M. Sanders, Angew. Chem Int Ed Engl., 1995,34, 1096.
  • [107] H.L. Anderson, J.K.M. Sanders, Angew. Chem. Int. Ed. Engl., 1990, 29, 1400.
  • [108] E. Hindin. C. Kirmaier, J.R. Diers, K. Tomizaki, M. Taniguchi! J.S. Lindsey. D.F. Bocian, D. Holten. J. Phys. Chem. B, 2004, 108, 8190.
  • [109] M. Ravikanth, Tetrahedron Lett., 2000, 41, 3709.
  • [110] N. Bampos, C.N. Woodburn, M.E. Welland, J.K.M. Sanders, Angew. Chem. Int Ed 1999 38 2780.
  • [111] M. Ravikanth. N. Agarwal, D. Kumaresan, Chem. Lett., 2000, 836.
  • [112] T. Ljungdahl, K. Pettersson, B. Abinsson, J. Martensson, J. Org. Chem., 2006, 71, 1677.
  • [113] E.M. Maya. P. Haisch, P. Vazquez, T. Torres, Tetrahedron. 1998. 54, 4397.
  • [114] E.M. Maya. P.Haisch, P. Vazquez, T. Torres, Chem. Eur. J., 1999, 5, 2004.
  • [115] K.W. Poon, W. Liu. P.K. Cha, Q. Yang. D. Chan, T.C.W. Mak, D.K.P. Ng, J. Org. Chem, 2001. 66, 1553
  • [116] H.Miyaji W. Sato, J.L. Sess.er. V.M. Lynch. Tetrahedron Lett., 2000, 41, .1369.
  • [117] W Sato H. Miyaji, J.L. Sessier, Tetrahedron Lett.. 2000. 41, 6731.
  • [118] M.J Cook, M.J. Heeney, Chem. Eur. J., 2000, 6. 3958
Typ dokumentu
Bibliografia
Identyfikator YADDA
bwmeta1.element.baztech-article-BUS5-0011-0014
JavaScript jest wyłączony w Twojej przeglądarce internetowej. Włącz go, a następnie odśwież stronę, aby móc w pełni z niej korzystać.