Skip to main content
SpringerLink
Log in

Metallosupramolecular Dye Assemblies

  • Chapter
  • First Online:
Supermolecular Dye Chemistry

Part of the book series: Topics in Current Chemistry ((TOPCURRCHEM,volume 258))

Abstract

Metallosupramolecular assemblies of dyes are of increasing interest as model systems for natural light harvesting and photosynthetic complexes as well as for potential applications in solar energy conversion, photonics and molecular electronics. Considerable efforts have been made in the past years to design novel metallosupramolecular dye architectures for such applications. Often in combination with other noncovalent interactions like hydrogen-bonding and π--π-stacking, metal-ion coordination has been utilized to achieve self-organization of dye building blocks into elaborate architectures with interesting optical and photophysical properties. Diverse metallosupramolecular dye assemblies -- macrocycles, polyhedra, polymers and dendrimers -- have been constructed in recent years by the metal-coordination approach. Here we review the recent advances in metallosupramolecular dye assemblies with particular attention to their thermodynamic stability and photophysical functionality. Emphasis is given to metal-ion mediated self-organization of porphyrin, metalloporphyrin and perylene bisimide dyes.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Log in via an institution

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Abbreviations

CSI-MS:

cold spray ionization mass spectrometry

DABCO:

1,4-diazabicyclo[2,2,2]octane

DFWM:

degenerate four-wave mixing

dppp:

1,3-bis(diphenylphosphano)propane

GPC:

gel permeation chromatography

LH:

light-harvesting

MLCT:

metal-to-ligand charge transfer

NBI:

naphthalene bisimide

PBI:

perylene bisimide

PGSE:

pulsed gradient spin echo

PPBI:

phenoxy-substituted perylene bisimide

PyP:

meso-(4-pyridyl)-porphyrin

SANS:

small-angle neutron scattering

TPP:

meso-tetraphenylporphyrin

tpy:

2,2′:6′,2′′-terpyridine

VPO:

vapor pressure osmometry

References

  1. Whitesides GM, Mathias JP, Seto CT (1991) Science 254:1312

    Google Scholar 

  2. Hu X, Ritz T, Damjanovič A, Autenrieth F, Schulten K (2002) Q Rev Biophys 35:1

    Google Scholar 

  3. Pullerits T, Sundstöm V (1996) Acc Chem Res 29:381

    Google Scholar 

  4. Law KY (1993) Chem Rev 93:449

    Google Scholar 

  5. Jones RM, Lu L, Helgeson R, Bergstedt TS, McBranch DW, Whitten DG (2001) Proc Natl Acad Sci USA 98:14769

    Google Scholar 

  6. Würthner F (2001) Angew Chem Int Ed 40:1037

    Google Scholar 

  7. Newman CR, Frisbie CD, da Silva Filho DA, Brédas J-L, Ewbank PC, Mann KR (2004) Chem Mater 16:4436

    Google Scholar 

  8. Kulkarni AP, Tonzola CJ, Babel A, Jenekhe SA (2004) Chem Mater 16:4556

    Google Scholar 

  9. Wöhrle D, Meissner D (1991) Adv Mater 3:129

    Google Scholar 

  10. Coakley KM, McGehee MD (2004) Chem Mater 16:4533

    Google Scholar 

  11. Li X, Sinks LF, Rybtchinski B, Wasielewski MR (2004) J Am Chem Soc 126:10810

    Google Scholar 

  12. Satake A, Kobuke Y (2005) Tetrahedron 61:13

    Google Scholar 

  13. Nagata N, Kugimiya S, Fujiwara E, Kobuke Y (2003) New J Chem 27:743

    Google Scholar 

  14. Leininger S, Olenyuk B, Stang PJ (2000) Chem Rev 100:853

    Google Scholar 

  15. Swiegers GF, Malefetse TJ (2000) Chem Rev 100:3483

    Google Scholar 

  16. Holliday BJ, Mirkin CA (2001) Angew Chem Int Ed 40:2022

    Google Scholar 

  17. Würthner F, You CC, Saha-Möller CR (2004) Chem Soc Rev 33:133

    Google Scholar 

  18. Würthner F (2004) Chem Commun 1564

    Google Scholar 

  19. Bookser BC, Bruice TC (1991) J Am Chem Soc 113:4208

    Google Scholar 

  20. Strachan JP, Gentemann S, Seth J, Kalsbeck WA, Lindsey JS, Holten D, Bocian DF (1997) J Am Chem Soc 119:11191

    Google Scholar 

  21. Gogan NJ, Siddiqui ZU (1970) J Chem Soc D 284

    Google Scholar 

  22. Gvishi R, Reisfeld R, Burshtein Z (1993) Chem Phys Lett 213:338

    Google Scholar 

  23. Langhals H, Karolin J, Johansson LBA (1998) J Chem Soc Faraday Trans 94:2919

    Google Scholar 

  24. Bhyrappa P, Bhavana P (2001) Chem Phys Lett 349:399

    Google Scholar 

  25. Würthner F, Thalacker C, Diele S, Tschierske C (2001) Chem Eur J 7:2245

    Google Scholar 

  26. Salbeck J, Kunkely H, Langhals H, Saalfrank RW, Daub J (1989) Chimia 43:6

    Google Scholar 

  27. Vogel GC, Stahlbush JR (1977) Inorg Chem 16:950

    Google Scholar 

  28. Würthner F, Thalacker C, Sautter A, Schärtl W, Ibach W, Hollricher O (2000) Chem Eur J 6:3871

    Google Scholar 

  29. Rudkevich DM, Verboom W, Reinhoudt DN (1995) J Org Chem 60:6585

    Google Scholar 

  30. El-Ghayoury A, Schenning APHJ, Meijer EW (2002) J Polym Sci: Part A: Polym Chem, 40:4020

    Google Scholar 

  31. Dobrawa R, Ballester P, Saha-Möller CR, Würthner F (2005) In: Newkome GR, Manners I, Schubert US (eds) ACS symposium book on metal-containing and metallo-supramolecular polymers and materials (in press)

    Google Scholar 

  32. Ercolani G (2003) J Am Chem Soc 125:16097

    Google Scholar 

  33. Drain CM, Lehn JM (1994) Chem Commun 2313

    Google Scholar 

  34. Drain CM, Goldberg I, Sylvain, I, Falber A (2005) Top Curr Chem 245:55

    Google Scholar 

  35. Stang PJ, Fan J, Olenyuk B (1997) Chem Commun 1453

    Google Scholar 

  36. Schmitz M, Leininger S, Fan J, Arif AM, Stang PJ (1999) Organometallics 18:4817

    Google Scholar 

  37. Fan J, Whiteford JA, Olenyuk B, Levin MD, Stang PJ, Fleischer EB (1999) J Am Chem Soc 121:2741

    Google Scholar 

  38. Slone RV, Hupp JT (1997) Inorg Chem 36:5422

    Google Scholar 

  39. Merlau ML, Mejia MP, Nguyen ST, Hupp JT (2001) Angew Chem Int Ed 40:4239

    Google Scholar 

  40. Iengo E, Milani B, Zangrando E, Geremia S, Alessio E (2000) Angew Chem Int Ed 39:1096

    Google Scholar 

  41. Iengo E, Zangrando E, Minatel R, Alessio E (2002) J Am Chem Soc 124:1003

    Google Scholar 

  42. Iengo E, Zangrando E, Alessio E (2003) Eur J Inorg Chem 2371

    Google Scholar 

  43. Würthner F, Sautter A, Thalacker C (2000) Angew Chem Int Ed 39:1243

    Google Scholar 

  44. Würthner F, Sautter A, Schilling J (2002) J Org Chem 67:3037

    Google Scholar 

  45. Sautter A, Schmid DG, Jung G, Würthner F (2001) J Am Chem Soc 123:5424

    Google Scholar 

  46. Würthner F, Sautter A (2000) Chem Commun 445

    Google Scholar 

  47. Würthner F, Sautter A, Schmid D, Weber PJA (2001) Chem Eur J 7:894

    Google Scholar 

  48. Würthner F, Sautter A (2003) Org Biomol Chem 1:240

    Google Scholar 

  49. Sautter A, Kaletaů BK, Schmid DG, Dobrawa R, Zimine M, Jung G, van Stokkum IHM, De Cola L, Williams RM, Würthner F (2005) J Am Chem Soc 127:6719

    Google Scholar 

  50. You CC, Würthner F (2003) J Am Chem Soc 125:9716

    Google Scholar 

  51. Stang PJ, Cao DH, Saito S, Arif AM (1995) J Am Chem Soc 117:6273

    Google Scholar 

  52. Sun SS, Lees AJ (2001) Inorg Chem 40:3154

    Google Scholar 

  53. Splan KE, Massari AM, Morris GA, Sun SS, Reina E, Nguyen ST, Hupp JT (2003) Eur J Inorg Chem 2348

    Google Scholar 

  54. Sun SS, Anspach JA, Lees AJ (2002) Inorg Chem 41:1862

    Google Scholar 

  55. Murguly E, Norsten TB, Branda NR (2001) Angew Chem Int Ed 40:1752

    Google Scholar 

  56. Qin B, Yao R, Zhao X, Tian H (2003) Org Biomol Chem 1:2187

    Google Scholar 

  57. Moriuchi T, Miyaishi M, Hirao T (2001) Angew Chem Int Ed 40:3042

    Google Scholar 

  58. Kobuke Y, Miyaji H (1994) J Am Chem Soc 116:4111

    Google Scholar 

  59. Stibrany RT, Vasudevan J, Knapp S, Potenza JA, Emge T, Schugar HJ (1996) J Am Chem Soc 118:3980

    Google Scholar 

  60. Gardner M, Guerin AJ, Hunter CA, Michelsen U, Rotger C (1999) New J Chem 23:309

    Google Scholar 

  61. Imamura T, Funatsu K, Ye S, Morioka Y, Uosaki K, Sasaki Y (2000) J Am Chem Soc 122:9032

    Google Scholar 

  62. Hunter CA, Sarson LD (1994) Angew Chem Int Ed Engl 33:2313

    Google Scholar 

  63. Chi X, Guerin AJ, Haycock RA, Hunter CA, Sarson LD (1995) J Chem Soc, Chem Commun 2567

    Google Scholar 

  64. Ikeda C, Tanaka Y, Fujihara T, Ishii Y, Ushiyama T, Yamamoto K, Yoshioka N, Inoue H (2001) Inorg Chem 40:3395

    Google Scholar 

  65. Fukushima K, Funatsu K, Ichimura A, Sasaki Y, Suzuki M, Fujihara T, Tsuge K, Imamura T (2003) Inorg Chem 42:3187

    Google Scholar 

  66. Tsuda A, Nakamura T, Sakamoto S, Yamaguchi K, Osuka A (2002) Angew Chem Int Ed 41:2817

    Google Scholar 

  67. Haycock RA, Hunter CA, James DA, Michelsen U, Sutton LR (2000) Org Lett 2:2435

    Google Scholar 

  68. Takahashi R, Kobuke Y (2003) J Am Chem Soc 125:2372

    Google Scholar 

  69. Ikeda C, Satake A, Kobuke Y (2003) Org Lett 5:4935

    Google Scholar 

  70. Michelsen U, Hunter CA (2000) Angew Chem Int Ed 39:764

    Google Scholar 

  71. Ciferri A (2002) Macromol Rapid Commun 23:511

    Google Scholar 

  72. Fleischer EB, Shachter AM (1991) Inorg Chem 30:3763

    Google Scholar 

  73. Burrell AK, Officer DL, Reis DCW, Wild KY (1998) Angew Chem Int Ed 37:114

    Google Scholar 

  74. Ogawa K, Kobuke Y (2000) Angew Chem Int Ed 39:4070

    Google Scholar 

  75. Ogawa K, Zhang T, Yoshihara K, Kobuke Y (2002) J Am Chem Soc 124:22

    Google Scholar 

  76. Ikeda C, Fujiwara E, Satake A, Kobuke Y (2003) Chem Commun 616

    Google Scholar 

  77. Twyman LJ, King ASH (2002) Chem Commun 910

    Google Scholar 

  78. You CC, Würthner F (2004) Org Lett 6:2401

    Google Scholar 

  79. Ayabe M, Yamashita K, Sada K, Shinkai S, Ikeda A, Sakamoto S, Yamaguchi K (2003) J Org Chem 68:1059

    Google Scholar 

  80. Hanack M, Dürr K, Lange A, Bacina JO, Pohmer J, Witke E (1995) Synthetic Metals 71:2275

    Google Scholar 

  81. Screen TEO, Thorne JRG, Denning RG, Bucknall DG, Anderson HL (2002) J Am Chem Soc 124:9712

    Google Scholar 

  82. Sauvage JP, Collin JP, Chambron JC, Guillerez S, Coudret C, Balzani V, Barigelletti F, De Cola L, Flamigni L (1994) Chem Rev 94:993

    Google Scholar 

  83. De Cola L, Belser P (1998) Coord Chem Rev 177:301

    Google Scholar 

  84. Ziessel R, Hissler M, El-Ghayoury A, Harriman A (1998) Coord Chem Rev 178–180:1251

    Google Scholar 

  85. Dobrawa R, Würthner F (2002) Chem Commun 1878

    Google Scholar 

  86. Dobrawa R, Lysetska M, Ballester P, Grüne M, Würthner F (2005) Macromolecules 38:1315

    Google Scholar 

  87. Dobrawa R, Kurth DG, Würthner F (2004) Polymer Preprints 45(1):378

    Google Scholar 

  88. Yu SC, Kwok CC, Chan WK, Che CM (2003) Adv Mater 15:1643

    Google Scholar 

  89. Phillips-McNaughton K, Groves JT (2003) Org Lett 5:1829

    Google Scholar 

  90. Herbst W, Hunger K (1997) Industrial organic pigments: production, properties, applications. VCH, Weinheim, p 390

    Google Scholar 

  91. Suh J, Oh E, Kim HC (1992) Synthetic Metals 48:325

    Google Scholar 

  92. Suh J, Moon SJ (1998) Bioorg Med Chem Lett 8:2751

    Google Scholar 

  93. Lee K, Suh MP, Suh J (1997) J Polym Sci Pol Chem 35:1825

    Google Scholar 

  94. Conn MM, Rebek JJr (1997) Chem Rev 97:1647

    Google Scholar 

  95. Ikeda A, Ayabe M, Shinkai S, Sakamoto S, Yamaguchi K (2000) Org Lett 2:3707

    Google Scholar 

  96. Anderson S, Anderson HL, Sanders JKM (1993) Acc Chem Res 26:469

    Google Scholar 

  97. Stulz E, Scott SM, Bond AD, Teat SJ, Sanders JKM (2003) Chem Eur J 9:6039

    Google Scholar 

  98. Stulz E, Scott SM, Bond AD, Otto S, Sanders JKM (2003) Inorg Chem 42:3086

    Google Scholar 

  99. Kieran AL, Bond AD, Belenguer AM, Sanders JKM (2003) Chem Commun 2674

    Google Scholar 

  100. Hwang IW, Cho HS, Jeong DH, Kim D, Tsuda A, Nakamura T, Osuka A (2003) J Phys Chem B 107:9977

    Google Scholar 

  101. Johnston MR, Latter MJ, Warrener RN (2002) Org Lett 4:2165

    Google Scholar 

  102. Reek JNH, Crossley MJ, Schenning APH, Bosman AW, Meijer EW (1998) Chem Commun 11

    Google Scholar 

  103. Felluga F, Tecilla P, Hillier L, Hunter CA, Licini G, Scrimin P (2000) Chem Commun 1087

    Google Scholar 

  104. Baldini L, Ballester P, Casnati A, Gomila RM, Hunter CA, Sansone F, Ungaro R (2003) J Am Chem Soc 125:14181

    Google Scholar 

  105. Tong Y, Hamilton DG, Meillon JC, Sanders JKM (1999) Org Lett 1:1343

    Google Scholar 

  106. Linke M, Chambron JC, Heitz V, Sauvage JP (1999) Chem Commun 2419

    Google Scholar 

  107. Andersson M, Linke M, Chambron JC, Davidsson J, Heitz V, Sauvage JP, Hammarström L (2000) J Am Chem Soc 122:3526

    Google Scholar 

  108. Johnstone KD, Bampos N, Sanders JKM, Gunter MJ (2003) Chem Commun 1396

    Google Scholar 

  109. Fedorova OA, Fedorov YV, Vedernikov AI, Yescheulova OV, Gromov SP, Alfimov MV, Kuz'mina LG, Churakov AV, Howard JAK, Zaitsev SY, Sergeeva TI, Möbius D (2002) New J Chem 26:543

    Google Scholar 

  110. Ajayaghosh A, Arunkumar E, Daub J (2002) Angew Chem Int Ed 41:1766

    Google Scholar 

  111. Camerel F, Strauch P, Antonietti M, Paul CFJ (2003) Chem Eur J 9:3764

    Google Scholar 

  112. Ambroise A, Li J, Yu L, Lindsey JS (2000) Org Lett 2:2563

    Google Scholar 

  113. Kuroda Y, Sugou K, Sasaki K (2000) J Am Chem Soc 122:7833

    Google Scholar 

  114. Wagner RW, Lindsey JS (1994) J Am Chem Soc 116:9759

    Google Scholar 

  115. Haycock RA, Yartsev A, Michelsen U, Sundtröm V, Hunter CA (2000) Angew Chem Int Ed 39:3616

    Google Scholar 

  116. Paul D, Wytko JA, Koepf M, Weiss J (2002) Inorg Chem 41:3699

    Google Scholar 

  117. Imahori H, Yoshizawa E, Yamada K, Hagiwara K, Okada T, Sakata Y (1995) J Chem Soc, Chem Commun 1133

    Google Scholar 

  118. Yamada K, Imahori H, Yoshizawa E, Gosztola D, Wasielewski MR, Sakata Y (1999) Chem Lett 235

    Google Scholar 

  119. Hunter CA, Hyde RK (1996) Angew Chem Int Ed Engl 35:1936

    Google Scholar 

  120. Andersson M, Linke M, Chambron JC, Davidsson J, Heitz V, Hammarström L, Sauvage JP (2002) J Am Chem Soc 124:4347

    Google Scholar 

  121. Zeng F, Zimmerman SC (1997) Chem Rev 97:1681

    Google Scholar 

  122. Bosman AW, Janssen HM, Meijer EW (1999) Chem Rev 99:1665

    Google Scholar 

  123. Grayson SM, Fréchet JMJ (2001) Chem Rev 101:3819

    Google Scholar 

  124. Huck WTS, Rohrer A, Anilkumar AT, Fokkens RH, Nibbering NMM, van Veggel FCJM, Reinhoudt DN (1998) New J Chem 22:165

    Google Scholar 

  125. Ballester P, Gomila RM, Hunter CA, King ASH, Twyman LJ (2003) Chem Commun 38

    Google Scholar 

  126. Nazeeruddin MdK, Humphry-Baker R, Berner D, Rivier S, Zuppiroli L, Graetzel M (2003) J Am Chem Soc 125:8790

    Google Scholar 

  127. Juris A, Balzani V, Barigelletti F, Campagna S, Belser P, von Zelewsky A (1988) Coord Chem Rev 84:85

    Google Scholar 

  128. Balzani V, Scandola F (1991) Supramolecular photochemistry. Ellis Horwood Ltd, Chichester

    Google Scholar 

  129. Holzwarth AR, Schaffner K (1994) Photosynth Res 41:225

    Google Scholar 

  130. Huber V, Katterle M, Lysetska M, Würthner F (2005) Angew Chem Int Ed 44:3147

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Institut für Organische Chemie, Universität Würzburg, Am Hubland, 97074, Würzburg, Germany

    Chang-Cheng You, Rainer Dobrawa, Chantu R. Saha-Möller & Frank Würthner

Authors
  1. Chang-Cheng You
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Rainer Dobrawa
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Chantu R. Saha-Möller
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Frank Würthner
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Frank Würthner .

Editor information

Frank Würthner

Rights and permissions

Reprints and permissions

About this chapter

Cite this chapter

You, CC., Dobrawa, R., Saha-Möller, C.R., Würthner, F. Metallosupramolecular Dye Assemblies . In: Würthner, F. (eds) Supermolecular Dye Chemistry. Topics in Current Chemistry, vol 258. Springer, Berlin, Heidelberg. https://doi.org/10.1007/b136668

Download citation

Publish with us

Policies and ethics

Search

Navigation