Abstract
The supramolecular organization of porphyrins using self-complementary coordination is reviewed. Complementarity affords large stability constants for coordination organization, and as a result various structural variations of porphyrin supramolecules were obtained. Dimeric porphyrins are of special interest as they mimic the special pair of the photosynthetic reaction centers. A very stable slipped cofacial dimer was obtained and the dimer effect on photoinduced charge separation is discussed. Macrocyclic porphyrin supramolecules were prepared as photosynthetic antenna models and rapid energy transfer rates among the components were estimated. Three-dimensional organization represents another type of approach to light-harvesting antenna systems. One- and two-dimensional arrays of porphyrins have also been prepared using this methodology. Energy and electron transfers along the array provide the basis for photonic and electronic applications. Introduction of molecular polarization in the array leads to the development of nonlinear optics materials. Photocurrent generation is enhanced by array formation on electrode surfaces.
Preview
Unable to display preview. Download preview PDF.
References
Alberts B, Johnson A, Lewis J, Raff M, Roberts K, Walter P (2001) Molecular biology of the cell. Garland, New York
Green BR, Parson WW (eds) (2003) Light-harvesting antennas in photosynthesis, vol 13. Kluwer, Dordrecht
Wasielewski MR (1992) Chem Rev 92:435
Gust D, Moore TA, Moore AL (2001) Acc Chem Res 34:40
Choi MS, Yamazaki T, Yamazaki I, Aida T (2004) Angew Chem Int Ed 43:150
Ogawa K, Kobuke Y (2003) Encyclopedia of nanoscience and nanotechnology X: 1. American Scientific, Los Angeles
Kobuke Y, Ogawa K (2003) Bull Chem Soc Jpn 76:689
Kobuke Y (2004) J Porphyrins Phthalocyanines 8:156
Satake A, Kobuke Y (2005) Tetrahedron 61:13
Wakao N, Yokoi N, Isoyama N, Hiraishi A, Shimada K, Kobayashi M, Kise H, Iwaki M, Ithoh S, Takaichi S, Sakurai Y (1996) Plant Cell Physiol 37:889
Kirksey CH, Hambright P, Storm CB (1969) Inorg Chem 8:2141
Deisenhofer J, Epp O, Miki K, Huber R, Michel H (1984) J Mol Biol 180:385
Yeates TO, Komiya H, Chirino A, Rees DC, Allen JP, Feher G (1988) Proc Natl Acad Sci USA 85:7993
Jordan P, Fromme P, Witt HT, Kukas O, Saenger W, Krauss N (2001) Nature 411:909
Zouni A, Witt HT, Kern J, Fromme P, Krauss N, Saenger W, Orth P (2001) Nature 409:739
McDermott G, Prince SM, Freer AA, Hawthornthwaite-Lawless AM, Papiz MZ, Cogdell RJ, Isaacs NW (1995) Nature 374:517
Karrasch S, Bullough PA, Ghosh R (1995) EMBO J 14:631
Roszak AW, Howard TD, Southall J, Gardiner AT, Law CJ, Isaacs NW, Cogdell RJ (2003) Science 302:1969
Papiz MZ, Prince SM, Howard T, Cogdell RJ, Isaacs NW (2003) J Mol Biol 326:1523
Bahatyrova S, Frese RN, Siebert CA, Olsen JD, Van Der Werf KO, Van Grondelle R, Niederman RA, Bullough PA, Otto C, Hunter CN (2004) Nature 430:1058
Hess S, Akesson E, Cogdell RJ, Pullerits T, Sundström V (1995) Biophys J 69:2211
Shreve AP, Trautman JK, Frank HA, Owens TG, Albrecht AC (1991) Biochim Biophys Acta 1058:280
Jimenez R, Dikshit SN, Bradforth SE, Fleming GR (1996) J Phys Chem 100:6825
Hu X, Ritz T, Damjanovic A, Schulten K (1997) J Phys Chem B 101:3854
Hess S, Chachisvilis M, Timpmann K, Jones MR, Hunter CN, Sundström V (1995) Proc Natl Acad Sci USA 92:12333
Beekman LMP, van Mourik F, Jones MR, Visser HM, Hunter CN, van Grondelle R (1994) Biochemistry 33:3143
Liu Z, Yan H, Wang K, Kuang T, Zhang J, Gui L, An X, Chang W (2004) Nature 428:287
Boekema EJ, Hifney A, Yakushevska AE, Piotrowski M, Keegstra W, Berry S, Michel KP, Pistorius EK, Kruip J (2001) Nature 412:745
Fleming GR, Martin JL, Breton J (1988) Nature 333:191
Deisenhofer J, Norris JR (eds) (1993) The photosynthetic reaction center I and II. Academic, New York
Michel-Beyerle ME (eds) (1996) The reaction center of photosynthetic bacteria. Springer, Berlin Heidelberg New York
Chang CK, Abdalmuhdi I (1983) J Org Chem 48:5388
Chang CK, Liu HY, Abdalmuhdi I (1984) J Am Chem Soc 106:2725
Meier H, Kobuke Y, Kugimiya S (1989) J Chem Soc Chem Commun 923
Osuka A, Nakajima S, Nagata T, Murayama K, Toriumi K (1991) Angew Chem Int Ed Engl 30:582
Kobuke Y, Miyaji H (1994) J Am Chem Soc 116:4111
Stibrany RT, Vasudevan J, Knapp S, Potenza JA, Emge T, Schugar HJ (1996) J Am Chem Soc 118:3980
Gerasimchuk NN, Mokhir AA, Rodgers KR (1998) Inorg Chem 37:5641
Kasha M, Rawls HR, El-bayyoumi MA (1965) Pure Appl Chem 11:371
Kobayashi T (ed) (1996) J-Aggregates. World Scientific, Singapore
Tabata M, Nishimoto J (1999) In: Kadish K, Smith KM, Guilard R (eds) The porphyrin handbook, vol 9. Academic, New York, p 221
Hunter CA, Sarson LD (1994) Angew Chem Int Ed Engl 33:2313
Nakamura Y, Hwang IW, Aratani N, Ahn TK, Ko DM, Takagi A, Kawai T, Matsumoto T, Kim D, Osuka A (2005) J Am Chem Soc 127:236
Mackay LG, Wylie RS, Sanders JKM (1994) J Am Chem Soc 116:3141
Vidal-Ferran A, Clyde-Watson Z, Bampos N, Sanders JKM (1997) J Org Chem 62:240
Mongin O, Schuwey A, Vallot MA, Gossauer A (1999) Tetrahedron Lett 40:8347
Peng X, Aratani N, Takagi A, Matsumoto T, Kawai T, Hwang IW, Ahn TK, Kim D, Osuka A (2004) J Am Chem Soc 126:4468
Li J, Ambroise A, Yang SI, Diers JR, Seth J, Wack CR, Bocian DF, Holten D, Lindsey JS (1999) J Am Chem Soc 121:8927
Anderson HL, Sanders JKM (1990) Angew Chem Int Ed Engl 29:1400
Anderson S, Anderson HL, Sanders JKM (1995) J Chem Soc Perkin Trans 1 2247
Yu L, Lindsey JS (2001) J Org Chem 66:7402
Rucareanu S, Mongin O, Schuwey A, Hoyler N, Gossauer A (2001) J Org Chem 66:4973
Anderson S, Anderson HL, Sanders JKM (1993) Acc Chem Res 26:469
Kim D, Osuka A (2004) Acc Chem Res 37:735
Holten D, Bocian DF, Lindsey JS (2002) Acc Chem Res 35:57
Takahashi R, Kobuke Y (2003) J Am Chem Soc 125:2372
Takahashi R, Kobuke Y (2005) J Org Chem 70:2745
Ohashi A, Satake A, Kobuke Y (2004) Bull Chem Soc Jpn 77:365
Ikeda C, Satake A, Kobuke Y (2003) Org Lett 5:4935
Chi X, Guerin AJ, Haycock RA, Hunter CA, Sarson LD (1995) Chem Commun 2567
Haycock RA, Hunter CA, James DA, Michelsen U, Sutton LR (2000) Org Lett 2:2435
Tsuda A, Nakamura T, Sakamoto S, Yamaguchi K, Osuka A (2002) Angew Chem Int Ed 41:2817
Hwang IW, Kamada T, Ahn TK, Ko DM, Nakamura T, Tsuda A, Osuka A, Kim D (2004) J Am Chem Soc 126:16187
Tsuda A, Hu H, Watanabe R, Aida T (2003) J Porphyrins Phthalocyanines 7:388
Tsuda A, Hu H, Tanaka R, Aida T (2005) Angew Chem Int Ed 44:4884
Iengo E, Zangrando E, Geremia S, Graff R, Kieffer B, Alessio E (2002) Chem Eur J 8:4670
Balaban TS, Goddard R, Linke-Schaetzel M, Lehn JM (2003) J Am Chem Soc 125:4233
Tsuda A, Sakamoto S, Yamaguchi K, Aida T (2003) J Am Chem Soc 125:15722
Tanaka A, Ryuno A, Okada S, Satake A, Kobuke Y (2005) Isr J Chem 45:281
Ikeda C, Tanaka Y, Fujihara T, Ishii Y, Ushiyama T, Yamamoto K, Yoshioka N, Inoue H (2001) Inorg Chem 40:3395
Funatsu K, Imamura T, Ichimura A, Sasaki Y (1998) Inorg Chem 37:1798
Fukushima K, Funatsu K, Ichimura A, Sasaki Y, Suzuki M, Fujihara T, Tsuge K, Imamura T (2003) Inorg Chem 42:3187
Kuramochi Y, Satake A, Kobuke Y (2004) J Am Chem Soc 126:8668
Shoji O, Okada S, Satake A, Kobuke Y (2005) J Am Chem Soc 127:2201
Shoji O, Tanaka H, Kawai T, Kobuke Y (2005) J Am Chem Soc 127:8598
Tanaka H, Kawai T (1997) J Vac Sci Technol B 15:602
Tanaka H, Kawai T (2003) Surf Sci 539:L531
Aratani N, Osuka A, Kim YH, Jeong DH, Kim D (2000) Angew Chem Int Ed 39:1458
Aratani N, Takagi A, Yanagawa Y, Matsumoto T, Kawai T, Yoon ZS, Kim D, Osuka A (2005) Chem Eur J 11:3389
Tsuda A, Osuka A (2001) Science 293:79
Tsuda A, Nakamura Y, Osuka A (2003) Chem Commun 1096
Anderson HL (1994) Inorg Chem 33:972
Taylor PN, Anderson HL (1999) J Am Chem Soc 121:11538
Cho HS, Jeong DH, Cho S, Kim D, Matsuzaki Y, Tanaka K, Tsuda A, Osuka A (2002) J Am Chem Soc 124:14642
Yoon DH, Lee SB, Yoo K-H, Kim J, Lim JK, Aratani N, Tsuda A, Osuka A, Kim D (2003) J Am Chem Soc 125:11062
Kuebler SM, Denning RG, Anderson HL (2000) J Am Chem Soc 122:339
Screen TEO, Thorne JRG, Denning RG, Bucknall DG, Anderson HL (2002) J Am Chem Soc 124:9712
Ikeda C, Yoon ZS, Park M, Inoue H, Kim D, Osuka A (2005) J Am Chem Soc 127:534
Ogawa K, Kobuke Y (2000) Angew Chem Int Ed 39:4070
Nomoto A, Kobuke Y (2002) Chem Commun 1104
Nomoto A, Mitsuoka H, Ozeki H, Kobuke Y (2003) Chem Commun 1074
Ogawa K, Ohashi A, Kobuke Y, Kamada K, Ohta K (2003) J Am Chem Soc 125:13356
Kobuke Y, Miyaji H (1996) Bull Chem Soc Jpn 69:3563
Nagata N, Kugimiya S, Fujiwara E, Kobuke Y (2003) New J Chem 743
Ikeda C, Satake A, Fujiwara E, Kobuke Y (2003) Chem Commun 616
Michelsen U, Hunter CA (2000) Angew Chem Int Ed 39:764
Morikawa S, Ikeda C, Ogawa K, Kobuke Y (2004) Lett Org Chem 1:6
Sugiura K, Tanaka H, Matsumoto T, Kawai T, Sakata Y (1999) Chem Lett 1193
McKeown NB (2002) Phthalocyanine materials: synthesis, structure and function. Cambridge University Press, Cambridge
Marks TJ (1985) Science 227:881
Torre G, Vazquez P, Agullo-Lopez F, Torres T (2004) Chem Rev 104:3723
Ishii K, Abiko S, Fujitsuka M, Ito O, Kobayashi N (2002) J Chem Soc Dalton Trans 1735
Cook MJ, Jafari-Fini A (1997) J Mater Chem 7:2327
Kobayashi N, Muranaka A (2000) Chem Commun 1855
Kameyama K, Satake A, Kobuke Y (2004) Tetrahedron Lett 45:7617
Kameyama K, Morisue M, Satake A, Kobuke Y (2005) Angew Chem Int Ed 44:4763
Ozeki H, Nomoto A, Ogawa K, Kobuke Y, Murakami M, Hosoda K, Ohtani M, Nakashima S, Miyasaka H, Okada T (2004) Chem Eur J 10:6393
Marcus RA (1959) Can J Chem 37:155
Marcus RA (1965) J Chem Phys 43:679
Rehm D, Weller A (1969) Ber Bunsenges Phys Chem 73:834
Schmidt JA, Liu JY, Bolton JR, Archer MD, Gadzekpo VPY (1989) J Chem Soc Faraday Trans 1 85:1027
Hwang IW, Park M, Ahn TK, Yoon ZS, Ko DM, Kim D, Ito F, Ishibashi Y, Khan SR, Nagasawa Y, Miyasaka H, Ikeda C, Takahashi R, Ogawa K, Satake A, Kobuke Y (2005) Chem Eur J 11:3753
Morandeira A, Vauthey E, Schuwey A, Gossauer A (2004) J Phys Chem A 108:5741
Furutsu D, Satake A, Kobuke Y (2005) Inorg Chem 44:4460
Prasad PN, Williams DJ (eds) (1991) Introduction to nonlinear optical effects in molecules and polymers. Wiley, New York
Zyss J (ed) (1994) Molecular nonlinear optics: materials, physics, and devices. Academic, Boston
Bosshard C, Sutter K, Prêtre P, Hulliger J, Flörsheimer M, Kaatz P, Günter P (1995) Organic nonlinear optical materials. Gordon and Breach, Amsterdam
Ogawa K, Kobuke Y (2002) J Am Chem Soc 124:22
Zhan X, Liu Y, Zhu D, Huang W, Gong Q (2001) Chem Mater 13:1540
Sheik-Bahae M, Said AA, Wei TH, Hagan DG, van Stryland EW (1990) IEEE J Quantum Electron 26:760
Drobizhev M, Karotki A, Kruk M, Rebane A (2002) Chem Phys Lett 355:175
Drobizhev M, Karotki A, Kruk M, Mamardashvili NZ, Rebane A (2002) Chem Phys Lett 361:504
Drobizhev M, Karotki A, Kruk M, Krivokapic A, Anderson HL, Rebane A (2003) Chem Phys Lett 370:690
Goyan RL, Cramb DT (2000) Photochem Photobiol 72:821
Kamada K, Ohta K, Iwase Y, Kondo K (2003) Chem Phys Lett 372:386
Iwase Y, Kondo K, Kamada K, Ohta K (2003) J Mater Chem 13:1573
Audebert P, Kamada K, Matsunaga K, Ohta K (2003) Chem Phys Lett 367:62
Antonov L, Kamada K, Ohta K, Kamounah S (2003) Phys Chem Chem Phys 5:1193
Kamada K, Matsunaga K, Yoshino A, Ohta K (2003) J Opt Soc Am B 20:529
Abbotto A, Beverina L, Bozio R, Facchetti A, Ferrante C, Pagani GA, Pedron D, Signorini R (2002) Org Lett 4:1495
Kim OK, Lee KS, Woo HY, Kim KS, He GS, Swiatkiewicz J, Prasad PN (2001) Chem Mater 13:4071
Chung SJ, Kim KS, Lin TC, He GS, Swiatkiewicz J, Prasad PN (1999) J Phys Chem B 103:10741
Abbotto A, Beverina L, Bozio R, Facchetti A, Ferrante C, Pagani GA, Pedronb D, Signorini R (2003) Chem Commun 2144
Belfield KD, Liu Y, Negres RA, Fan M, Pan G, Hagan DJ, Hernandez FE (2002) Chem Mater 14:3663
Porres L, Mongin O, Katan C, Charlot M, Pons T, Mertz J, Blanchard-Desce M (2004) Org Lett 6:47
Ogawa K, Ohashi A, Kobuke Y, Kamada K, Ohta K (2005) J Phys Chem B 109:22003
Nazeeruddin MK, Kay A, Rodicio I, Humphry-Baker R, Müller E, Liska P, Vlachopoulos N, Grätzel M (1993) J Am Chem Soc 115:6382
Hagfeldt A, Grätzel M (1995) Chem Rev 95:49
Stuart L (2002) Semiconductor electrodes and photoelectrochemistry. In: Bard AJ, Stratmann M (eds) Encyclopedia of electrochemistry, vol 6. Wiley-VCH, Weinheim
Morisue M, Yamatsu S, Haruta N, Kobuke Y (2005) Chem Eur J 11:5563
Author information
Authors and Affiliations
Corresponding author
Editor information
Rights and permissions
About this chapter
Cite this chapter
Kobuke, Y. Porphyrin Supramolecules by Self-Complementary Coordination. In: Alessio, E. (eds) Non-Covalent Multi-Porphyrin Assemblies. Structure and Bonding, vol 121. Springer, Berlin, Heidelberg. https://doi.org/10.1007/430_023
Download citation
DOI: https://doi.org/10.1007/430_023
Published:
Publisher Name: Springer, Berlin, Heidelberg
Print ISBN: 978-3-540-32542-0
Online ISBN: 978-3-540-32543-7
eBook Packages: Chemistry and Materials ScienceChemistry and Material Science (R0)