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Supramolecules Based on Porphyrins

  • Hiroko YamadaEmail author
  • Tetsuo Okujima
  • Noboru Ono
Chapter
Part of the Topics in Heterocyclic Chemistry book series (TOPICS, volume 17)

Abstract

As porphyrins and phthalocyanines possess unique electronic, magnetic and optical properties, supramolecular assembly based on them is subject to intense research targets. Herein, the reviewers focus on the supramolecular architectures of porphyrins, which enable their use as electronic and optical functional materials such as third-order optical susceptibilities, photoenergy conversion systems, and organic field-effect transistors.

Optical and electronic devices ππ stacking interaction Porphyrin van der Waals interaction  

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References

  1. 1.
    Special issue on supramolecular chemistry and self-assembly (2002) Science 295:2395 Google Scholar
  2. 2.
    Special issue on supramolecular approaches to organic electronics and nanotechnology (2006) Adv Mater 18:1227 Google Scholar
  3. 3.
    van Nostrum CF, Nolte RJM (1996) Chem Commun, p 2385 Google Scholar
  4. 4.
    Elemans JAAW, van Hameren R, Nolte RJM, Rowan AE (2006) Adv Mater 18:1251 CrossRefGoogle Scholar
  5. 5.
    Saito T, Sisk W, Kobayashi T, Suzuki S, Iwayanagi T (1993) J Phys Chem 97:8026 CrossRefGoogle Scholar
  6. 6.
    Tamiaki H (1996) Coord Chem Rev 148:183 CrossRefGoogle Scholar
  7. 7.
    Hu X, Ritz T, Damjanoviæ A, Schuten K (1997) J Phys Chem B 101:3854 CrossRefGoogle Scholar
  8. 8.
    Satake A, Kobuke Y (2007) Org Biomol Chem 5:1679 CrossRefGoogle Scholar
  9. 9.
    Nakamura Y, Aratani N, Osuka A (2007) Chem Soc Rev 36:831 CrossRefGoogle Scholar
  10. 10.
    Kelly RF, Goldsmith RH, Wasielewski MR (2007) J Am Chem Soc 129:6384 CrossRefGoogle Scholar
  11. 11.
    Sanders JKM (1996) In: Atwood JL, Davies JED, MacNicol DD, Vögtle F, Lehn J-M (eds) Comprehensive Supramolecular Chemistry, vol 9. Pergamon, Oxford, p 131 Google Scholar
  12. 12.
    Sanders JKM (2000) In: Kadish KM, Smith KM, Roger G (eds) The Porphyrin Handbook, vol 3. Academic Press, San Diego, p 347 Google Scholar
  13. 13.
    Chambron JC, Herz V, Sauvage JP (2000) In: Kadish KM, Smith KM, Roger G (eds) The Porphyrin Handbook, vol 6. Academic Press, San Diego, p 1 Google Scholar
  14. 14.
    Satake A, Kobuke Y (2005) Tetrahedron 61:13 CrossRefGoogle Scholar
  15. 15.
    Balaban TS (2005) Acc Chem Res 38:612 CrossRefGoogle Scholar
  16. 16.
    Iengo E, Zangrando E, Alessio E (2006) Acc Chem Res 39:841 CrossRefGoogle Scholar
  17. 17.
    Rucareanu S, Schuwey A, Gossauer A (2006) J Am Chem Soc 128:3396 CrossRefGoogle Scholar
  18. 18.
    Hoffmann M, Wilson CJ, Odell B, Anderson HL (2007) Angew Chem Int Ed 46:3122 CrossRefGoogle Scholar
  19. 19.
    Kobuke Y, Miyaji H (1994) J Am Chem Soc 116:4111 CrossRefGoogle Scholar
  20. 20.
    Kobuke Y, Ogawa K (2003) Bull Chem Soc Jpn 76:689 CrossRefGoogle Scholar
  21. 21.
    Kameyama K, Morisue M, Satake A, Kobuke Y (2005) Angew Chem Int Ed 44:4763 CrossRefGoogle Scholar
  22. 22.
    Maeda C, Shinokubo H, Osuka A (2007) Org Lett 9:2493 CrossRefGoogle Scholar
  23. 23.
    Kamada T, Aratani N, Ikeda T, Shibata N, Higuchi Y, Wakamiya A, Yamaguchi S, Kim KS, Yoon ZS, Kim D, Osuka A (2006) J Am Chem Soc 128:7670 CrossRefGoogle Scholar
  24. 24.
    Matano Y, Matsumoto K, Terasaka Y, Hotta H, Araki Y, Ito O, Shiro M, Sasamori T, Tokitoh N, Imahori H (2007) Chem Eur J 13:891 CrossRefGoogle Scholar
  25. 25.
    Sessler JL, Jayawickramarajah J, Gouloumis A, Torres T, Guldi DM, Maldonado S, Stevenson KJ (2005) Chem Commun, p 1892 Google Scholar
  26. 26.
    Shirakawa M, Kawano S, Fujita N, Sada K, Shinkai S (2003) J Org Chem 68:5037 CrossRefGoogle Scholar
  27. 27.
    Shirakawa M, Fujita N, Shinkai S (2003) J Am Chem Soc 125:9902 CrossRefGoogle Scholar
  28. 28.
    Shirakawa M, Fujita N, Shinkai S (2005) J Am Chem Soc 127:4164 CrossRefGoogle Scholar
  29. 29.
    O'Flaherty SM, Hold SV, Cook MJ, Torres T, Chen Y, Hanack M, Blau WJ (2003) Adv Mater 15:19 CrossRefGoogle Scholar
  30. 30.
    Chou J-H, Kosal ME, Nalwa HS, Rakow NA, Suslick KS (2000) In: Kadish KM, Smith KM, Roger G (eds) The Porphyrin Handbook, vol 6. Academic Press, San Diego, p 73 Google Scholar
  31. 31.
    Drobizhev M, Stepanenko Y, Dzenis Y, Karotki A, Rebane A, Taylor PN, Anderson HL (2004) J Am Chem Soc 126:15352 CrossRefGoogle Scholar
  32. 32.
    Drobizhev M, Stepanenko Y, Dzenis Y, Karotki A, Rebane A, Taylor PN, Anderson HL (2005) J Phys Chem B 109:7223 CrossRefGoogle Scholar
  33. 33.
    Karotki A, Drobizhev M, Dzenis Y, Taylor PN, Anderson HL, Rebane A (2004) Phys Chem Chem Phys 6:7 CrossRefGoogle Scholar
  34. 34.
    Ahn TK, Kim KS, Kim DY, Noh SB, Aratani N, Ikeda C, Osuka A, Kim D (2006) J Am Chem Soc 128:1700 CrossRefGoogle Scholar
  35. 35.
    Kim DY, Ahn TK, Kwon JH, Kim D, Ikeue T, Aratani N, Osuka A, Shigeiwa M, Maeda S (2005) J Phys Chem A 109:2996 CrossRefGoogle Scholar
  36. 36.
    Inokuma Y, Ono N, Uno H, Kim DY, Noh SB, Kim D, Osuka A (2005) Chem Commun, p 3782 Google Scholar
  37. 37.
    Screen TEO, Thorne JRG, Denning RG, Bucknell DG, Anderson HL (2002) J Am Chem Soc 124:9712 CrossRefGoogle Scholar
  38. 38.
    Drobizhev M, Stepanenko Y, Rebane A, Wilson CJ, Screen TEO, Anderson HL (2006) J Am Chem Soc 128:12432 CrossRefGoogle Scholar
  39. 39.
    Ogawa K, Ohashi A, Kobuke Y, Kamada K, Ohta K (2003) J Am Chem Soc 125:13356 CrossRefGoogle Scholar
  40. 40.
    Ogawa K, Ohashi A, Kobuke Y, Kamada K, Ohta K (2005) J Phys Chem B 109:22003 CrossRefGoogle Scholar
  41. 41.
    Tanihara J, Ogawa K, Kobuke Y (2006) J Photochem Photobiol A 178:140 CrossRefGoogle Scholar
  42. 42.
    Ogawa K, Hasegawa H, Inaba Y, Kobuke Y, Inouye H, Kanemitsu Y, Kohno E, Hirano T, Ogura S, Okura I (2006) J Med Chem 49:2276 CrossRefGoogle Scholar
  43. 43.
    Dy JT, Ogawa K, Satake A, Ishizumi A, Kobuke Y (2007) Chem Eur J 13:3491 CrossRefGoogle Scholar
  44. 44.
    Collini E, Ferrante C, Bozio R (2005) J Phys Chem B 109:2 CrossRefGoogle Scholar
  45. 45.
    Ray PC, Sainudeen Z (2006) J Phys Chem A 110:12342 CrossRefGoogle Scholar
  46. 46.
    Grätzel M (2004) J Photochem Photobiol A 164:3 CrossRefGoogle Scholar
  47. 47.
    Peumans P, Yakimov A, Forrest SR (2003) J Appl Phys 93:3693 CrossRefGoogle Scholar
  48. 48.
    O'Regan B, Grätzel M (1991) Nature 353:737 CrossRefGoogle Scholar
  49. 49.
    Campbell WM, Burrell AK, Officer DL, Jolley KW (2004) Coord Chem Rev 248:1363 CrossRefGoogle Scholar
  50. 50.
    Schmidt-Mende L, Campbell WM, Wang Q, Jolley KW, Officer DL, Nazeeruddin MK, Grätzel M (2005) ChemPhysChem 6:1253 CrossRefGoogle Scholar
  51. 51.
    Wang Q, Campbell WM, Bonfantani EE, Jolley KW, Officer DL, Walsh PJ, Gordon K, Humphry-Baker R, Nazeeruddin MK, Grätzel M (2005) J Phys Chem B 109:15397 CrossRefGoogle Scholar
  52. 52.
    Campbell WM, Jolley KW, Wagner P, Wagner K, Walsh PJ, Gordon KC, Schmidt-Mende L, Nazeeruddin MK, Wang Q, Grätzel M, Officer DL (2007) J Phys Chem C 111:11760 CrossRefGoogle Scholar
  53. 53.
    Tang CW (1986) Appl Phys Lett 48:183 CrossRefGoogle Scholar
  54. 54.
    Yu G, Gao J, Hummelen JC, Wudl F, Heeger AJ (1995) Science 270:1789 CrossRefGoogle Scholar
  55. 55.
    Brabec CJ, Sariciftci NS, Hummelen JC (2001) Adv Funct Mater 11:15 CrossRefGoogle Scholar
  56. 56.
    Nelson J (2002) Curr Opin Solid State Mater Sci 6:87 CrossRefGoogle Scholar
  57. 57.
    Goetzberger A, Hebling C, Schock HW (2003) Mater Sci Eng R 40:1 CrossRefGoogle Scholar
  58. 58.
    Forrest SR (2004) Nature 428:911 CrossRefGoogle Scholar
  59. 59.
    Yamashita K (1982) Chem Lett 1085 Google Scholar
  60. 60.
    Yamashita K, Harima Y, Kubota H, Suzuki H (1987) Bull Chem Soc Jpn 60:803 CrossRefGoogle Scholar
  61. 61.
    Wienke J, Schaafsma TJ, Goossens A (1999) J Phys Chem B 103:2702 CrossRefGoogle Scholar
  62. 62.
    Shao Y, Yang Y (2005) Adv Mater 17:2841 CrossRefGoogle Scholar
  63. 63.
    Sato Y, Niinomi T, Hashiguchi M, Matsuo Y, Nakamura E (2007) SPIE Proc 6656 Google Scholar
  64. 64.
    Gust D, Moore TA (2000) In: Kadish KM, Smith KM, Roger G (eds) The Porphyrin Handbook, vol 8. Academic Press, San Diego, p 153 Google Scholar
  65. 65.
    Wojaczyński J, Latos-Grażyński L (2000) Coord Chem Rev 204:113 CrossRefGoogle Scholar
  66. 66.
    El-Khouly ME, Ito O, Smith PM, D'Souza F (2004) J Photochem Photobiol C 5:79 CrossRefGoogle Scholar
  67. 67.
    Mateo-Alonso A, Sooambar C, Maurizio P (2006) D R Chimie 9:944 CrossRefGoogle Scholar
  68. 68.
    D'Souza F, Ito O (2005) Coord Chem Rev 249:1410 CrossRefGoogle Scholar
  69. 69.
    Konishi T, Ikeda A, Shinkai S (2005) Tetrahedron 61:4881 CrossRefGoogle Scholar
  70. 70.
    Bonifazi D, Enger O, Diederich F (2007) Chem Soc Rev 36:390 CrossRefGoogle Scholar
  71. 71.
    Sun Y, Drovetskaya T, Bolskar RD, Bau R, Boyd PDW, Reed CA (1997) J Org Chem 62:3642 CrossRefGoogle Scholar
  72. 72.
    Boyd PDW, Hodgson MC, Rickard CEF, Oliver AG, Chaker L, Brothers PJ, Bolskar RD, Tham FS, Reed CA (1999) J Am Chem Soc 121:10487 CrossRefGoogle Scholar
  73. 73.
    Sun D, Tham FS, Reed CA, Chaker L, Burgess M, Boyd PDW (2000) J Am Chem Soc 122:10704 CrossRefGoogle Scholar
  74. 74.
    Zheng J-Y, Tashiro K, Hirabayashi Y, Kinbara K, Saigo K, Aida T, Sakamoto S, Yasmaguchi K (2001) Angew Chem Int Ed 40:1857 CrossRefGoogle Scholar
  75. 75.
    Sun D, Tham FS, Reed CA, Boyd PDW (2002) Proc Natl Acad Sci USA 99:5088 CrossRefGoogle Scholar
  76. 76.
    Wang Y-B, Lin Z (2003) J Am Chem Soc 125:6072 CrossRefGoogle Scholar
  77. 77.
    Ayabe M, Ikeda A, Kubo Y, Takeuchi M, Shinkai S (2002) Angew Chem Int Ed 41:2790 CrossRefGoogle Scholar
  78. 78.
    Boyd PDW, Reed CA (2005) Acc Chem Res 38:235 CrossRefGoogle Scholar
  79. 79.
    Hasobe T, Imahori H, Kamat PV, Fukuzumi S (2003) J Am Chem Soc 125:14962 CrossRefGoogle Scholar
  80. 80.
    Hasobe T, Imahori H, Fukuzumi S, Kamat PV (2003) J Phys Chem B 107:12105 CrossRefGoogle Scholar
  81. 81.
    Hasobe T, Kamat PV, Absalom MA, Kashiwagi Y, Sly J, Crossley MJ, Hosomizu K, Imahori H, Fukuzumi S (2004) J Phys Chem B 108:12865 CrossRefGoogle Scholar
  82. 82.
    Hasobe T, Kashiwagi Y, Absalom MA, Sly J, Hosomizu K, Crossley MJ, Imahori H, Kamat PV, Fukuzumi S (2004) Adv Mater 16:975 CrossRefGoogle Scholar
  83. 83.
    Hasobe T, Imahori H, Kamat PV, Ahn TK, Kim SK, Kim D, Fujimoto A, Hirakawa T, Fukuzumi S (2005) J Am Chem Soc 127:1216 CrossRefGoogle Scholar
  84. 84.
    Imahori H, Fujimoto A, Kang S, Hotta H, Yoshida K, Umeyama T, Matano Y, Isoda S (2005) Adv Mater 17:1727 CrossRefGoogle Scholar
  85. 85.
    Hasobe T, Imahori H, Kamat PV, Ahn TK, Kim SK, Kim D, Fujimoto A, Hirakawa T, Fukuzumi S (2005) J Am Chem Soc 127:1216 CrossRefGoogle Scholar
  86. 86.
    Imahori H, Mitamura K, Shibano Y, Umeyama T, Matano Y, Yoshida K, Isoda S, Araki Y, Ito O (2006) J Phys Chem B 110:11399 CrossRefGoogle Scholar
  87. 87.
    Hasobe T, Hattori S, Kamat PV, Fukuzumi S (2006) Tetrahedron 62:1937 CrossRefGoogle Scholar
  88. 88.
    Imahori H, Mitamura K, Umeyama T, Hosomizu K, Matano Y, Yoshida K, Isoda S (2006) Chem Commun, p 406 Google Scholar
  89. 89.
    Imahori H, Fujimoto A, Kang S, Hotta H, Yoshida K, Umeyama T, Matano Y, Isoda S (2006) Tetrahedron 62:1955 CrossRefGoogle Scholar
  90. 90.
    Kang S, Umeyama T, Ueda M, Matano Y, Hotta H, Yoshida K, Isoda S, Shiro M, Imahori H (2006) Adv Mater 18:2549 CrossRefGoogle Scholar
  91. 91.
    Imahori H (2007) Bull Chem Soc Jpn 80:621 CrossRefGoogle Scholar
  92. 92.
    Imahori H (2007) J Mater Chem 17:31 CrossRefGoogle Scholar
  93. 93.
    Hasobe T, Fukuzumi S, Hattori S, Kamat PP (2007) Chem Asian J 2:265 CrossRefGoogle Scholar
  94. 94.
    Hasobe T, Fukuzumi S, Kamat PV (2006) J Phys Chem B 110:25477 CrossRefGoogle Scholar
  95. 95.
    Hasobe T, Fukuzumi S, Kamat PV (2005) J Am Chem Soc 127:11884 CrossRefGoogle Scholar
  96. 96.
    Nomoto A, Kobuke Y (2002) Chem Commun, p 1104 Google Scholar
  97. 97.
    Nomoto A, Mitsuoka H, Ozeki H, Kobuke Y (2003) Chem Commun, p 1074 Google Scholar
  98. 98.
    Morisue M, Kalita D, Haruta N, Kobuke Y (2007) Chem Commun, p 2348 Google Scholar
  99. 99.
    Drain CM (2002) PNAS 99:5178 CrossRefGoogle Scholar
  100. 100.
    Guldi DM, Zilbermann I, Anderson G, Li A, Balbinot D, Jux N, Hatzimarinaki M, Hirsch A, Prato M (2004) Chem Commun, p 726 Google Scholar
  101. 101.
    Guldi D, Rahman GMA, Jux N, Tagmatarchis N, Prato M (2004) Angew Chem Int Ed 43:5526 CrossRefGoogle Scholar
  102. 102.
    Guldi DM (2005) J Phys Chem B 109:11432 CrossRefGoogle Scholar
  103. 103.
    Ehli C, Rahman GMA, Jux N, Balbinot D, Guldi DM, Paolucci F, Marcaccio M, Paolucci D, Melle-Franco M, Zerbetto F, Campidelli S, Prato M (2006) J Am Chem Soc 128:11222 CrossRefGoogle Scholar
  104. 104.
    Ikeda A, Hatano T, Shinkai S, Akiyama T, Yamada S (2001) J Am Chem Soc 123:4855 CrossRefGoogle Scholar
  105. 105.
    Ikeda A, Hatano T, Konishi T, Kikuvhi J-I, Shinkai S (2003) Tetrahedron 59:3537 CrossRefGoogle Scholar
  106. 106.
    Konishi T, Ikeda A, Asai M, Hatano T, Shinkai S, Fujitsuka M, Ito O, Tsuchiya Y, Kikuchi J-I (2003) J Phys Chem B 107:11261 CrossRefGoogle Scholar
  107. 107.
    Bae A-H, Hatano T, Sugiyasu K, Kishida T, Takeuchi M, Shinkai S (2005) Tetrahedron Lett 46:3169 CrossRefGoogle Scholar
  108. 108.
    Murphy AR, Fréchet JMJ (2007) Chem Rev 107:1066 CrossRefGoogle Scholar
  109. 109.
    Würthner F, Schmidt R (2006) ChemPhysChem 7:793 CrossRefGoogle Scholar
  110. 110.
    Loo Y-L (2007) AIChE J 53:1066 CrossRefGoogle Scholar
  111. 111.
    Takimiya K, Kunugi Y, Otsubo T (2007) Chem Lett 36:578 CrossRefGoogle Scholar
  112. 112.
    Payne MM, Parkin SR, Anthony JE, Kuo C-C, Jackson TN (2005) J Am Chem Soc 127:4986 CrossRefGoogle Scholar
  113. 113.
    Ando S, Murakami R, Nishida J, Tada H, Inoue Y, Tokito S, Yamashita Y (2005) J Am Chem Soc 127:14996 CrossRefGoogle Scholar
  114. 114.
    Sakamoto Y, Suzuki T, Kobayashi M, Gao Y, Fukai Y, Inoue Y, Sato F, Tokito S (2004) J Am Chem Soc 126:8138 CrossRefGoogle Scholar
  115. 115.
    Yamamoto T, Takimiya K (2007) J Am Chem Soc 129:2224 CrossRefGoogle Scholar
  116. 116.
    Meng H, Sun F, Goldfiner MB, Gao F, Londono DJ, Marshal WJ, Blackman GS, Dobbs KD, Keys DE (2006) J Am Chem Soc 128:9304 CrossRefGoogle Scholar
  117. 117.
    Bao Z, Lovinger AJ, Dodabalapur A (1997) Adv Mater 9:42 CrossRefGoogle Scholar
  118. 118.
    Zhang J, Wang J, Wang H, Yan D (2004) Appl Phys Lett 84:142 CrossRefGoogle Scholar
  119. 119.
    Zeis R, Siegrist T, Kloc C (2005) Appl Phys Lett 86:022103 CrossRefGoogle Scholar
  120. 120.
    Xiao K, Liu Y, Huang X, Xu Y, Yu G, Zhu D (2003) J Phys Chem B 107:9226 CrossRefGoogle Scholar
  121. 121.
    Chen Y, Su W, Bai M, Jianzhuang J, Liu X, Wang L, Wang S (2005) J Am Chem Soc 127:15700 CrossRefGoogle Scholar
  122. 122.
    Bao Z, Lovinger AJ, Brown J (1998) J Am Chem Soc 120:207 CrossRefGoogle Scholar
  123. 123.
    de Oteyza DG, Barrena E, Ossó J, Sellner S, Dosch H (2006) J Am Chem Soc 128:15052 CrossRefGoogle Scholar
  124. 124.
    Tang Q, Li H, Liu Y, Hu W (2006) J Am Chem Soc 126:14634 CrossRefGoogle Scholar
  125. 125.
    Ito S, Murashima T, Uno H, Ono N (1998) Chem Commun, p 1661 Google Scholar
  126. 126.
    Aramaki S, Sakai Y, Ono N (2004) Appl Phys Lett 84:2085 CrossRefGoogle Scholar
  127. 127.
    Shea PB, Pattison LR, Kawano M, Chen C, Chen J, Petroff P, Matin DC, Yamada H, Ono N, Kanicki J (2007) Synth Metals 157:190 CrossRefGoogle Scholar
  128. 128.
    Shea PB, Kanicki J, Pattison LR, Petroff P, Kawano M, Yamada H, Ono N (2006) J Appl Phys 100:034502 CrossRefGoogle Scholar
  129. 129.
    Shea PB, Chen C, Kanicki J, Pattison LR, Petroff P (2007) Appl Phys Lett 90:233107 CrossRefGoogle Scholar

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© Springer-Verlag Berlin Heidelberg 2008

Authors and Affiliations

  1. 1.Department of Chemistry and Biology, Graduate School of Science and EngineeringEhime UniversityMatsuyamaJapan
  2. 2.PRESTOJSTKawaguchiJapan

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