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Advanced Light Emitting Dyes: Monomers, Oligomers, and Polymers

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Applied Fluorescence in Chemistry, Biology and Medicine

Abstract

Substances emitting light in response to external stimuli (light, electric current, X-ray…) are known as luminescent materials or luminophores [1, 2]. Luminophores occupy a special position in materials science because they are generally associated with high-technology applications such as single-molecule spectroscopy [3], fluorescent solar collectors [4], optical switches [5], lasers [6, 7], fluorescent brighteners [8], labelled antibodies [9] and electroluminescent diodes [10–14]. These examples illustrate the diversity of applications and stress the importance of a unified approach toward “organic” and “polymeric” dye stuff chemistry.

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References

  1. Zollinger, H.; „Color Chemistry“ VCH Verlagsgesellschaft, Weinheim, 1987.

    Google Scholar 

  2. Krassovitskii, B.M.; Bolotin, B.M.; „Organic Luminescent Materials“, VCH Verlags- gesellshaft, Weinheim, 1988.

    Google Scholar 

  3. Basché, T.; Moerner, W.E.; Orrit, M.; Wild, U.P.; „Single-Molecule Optical Detection, Imaging and Spectroscopy“ VCH Verlagsgesellshaft, Weinheim, 1997, and references cited therein.

    Google Scholar 

  4. Seybold, G.; Wagenblast, G.; Dyes and Pigments, 1989,11,303.

    Article  Google Scholar 

  5. O’Neil, M.P.; Niemczyk, M.P.; Svec, W.A.; Gosztola, D.; Gaines III, G.L.; Wasielewski, M.R.; Science, 1992,257,63.

    Article  Google Scholar 

  6. Burgdorff, C.; Löhmannsröben, H.G.; Reisfeld, R.; Chem. Phys. Lett. 1992,197,358.

    Article  CAS  Google Scholar 

  7. Gvishi, R.; Reisfeld, R.; Burshtein, Z.; Chem. Phys. Lett. 1993,213,338.

    Article  CAS  Google Scholar 

  8. Christie, R.M.; Polym. Int. 1994,34,351.

    Article  CAS  Google Scholar 

  9. Mayer, A.; Neuenhofer, S.; Angew. Chem. Int. Ed. Engl. 1994,33,1044.

    Article  Google Scholar 

  10. Tasch, S.; Niko, A.; Leising, G.; Scherf, U.; Appl. Phys. Lett. 1996,68,1090.

    Article  CAS  Google Scholar 

  11. Tasch, S.; Hochfilzer, C.; List, J.W.E.; Leising, G.; Geerts Y.; Schlichting, P.; Rohr, U.; Scherf, U.; Müllen, K.; Phys. Rev. B. submitted.

    Google Scholar 

  12. Tasch, S.; Hochfilzer, C.; List, J.W.E.; Leising, G.; Geerts Y.; Schlichting, P.; Rohr, U.; Scherf, U.; Müllen, K.; Appl. Phys. Lett, submitted.

    Google Scholar 

  13. Huber, J.; Müllen, K.; Salbeck, J.; Schenk, H.; Scherf, U.; Stehlin, T.; Stern, R.; Acta Polym. 1994,45,244.

    Article  CAS  Google Scholar 

  14. Conwell, E.; Trends Polym. Sci. 1997,5,218.

    CAS  Google Scholar 

  15. Klärner, G.; Müller, M.; Morgenroth, F.; Wehmeier, M.; Sozka-Guth, T.; Müllen, K.; Synth. Met. 1997,84,297.

    Article  Google Scholar 

  16. Geerts, Y.; Klärner, G.; Müllen, K.; Hydrocarbon Oligomers In Electronic Materials: The Oligomer Approach, Müllen, K. and Wegner, G. (eds.), VCH, Weinheim, 1997.

    Google Scholar 

  17. Electronic Materials: The Oligomer Approach, Müllen, K. and Wegner, G. (eds.), VCH, Weinheim, 1997.

    Google Scholar 

  18. Baumgarten, M.; Bunz, U.; Scherf, U.; Müllen, K.; Organic Synthesis and Materials Science In Molecular Engineering for Advanced Materials, Becher, J. and Schaumburg, K. (eds.), Kluwer Academic Publishers, 1995.

    Google Scholar 

  19. Müllen, K; Pure & Appl. Chem. 1993,65,89.

    Article  Google Scholar 

  20. Klärner, G.; Former, C.; Yan, X.; Richert, R.; Müllen, K; Adv. Mater. 1996,8,932.

    Article  Google Scholar 

  21. Scherf, U.; Müllen, K; Synthesis, 1992,23.

    Google Scholar 

  22. Dotcheva, D.; Klapper, M.; Müllen, K; Macromol. Chem. Phys. 1994,195,1905.

    Google Scholar 

  23. Müllen, K; Quante, H.; Benfaremo, N.; „Perylene Polymers“ in „Polymeric Materials Encyclopedia“, Salamone, J.C. ed., CRC Press, Boca Raton, 1996.

    Google Scholar 

  24. Quante, H.; Schlichting, P.; Rohr, U.; Geerts, Y.; Müllen, K; Macromol. Chem. Phys. 1996, 197,4029.

    Article  CAS  Google Scholar 

  25. Geerts, Y.; Keller, U.; Scherf, U.; Schneider, M.; Müllen, K.; Am. Chem. Soc., Polym. Prep. 1997,38,315.

    CAS  Google Scholar 

  26. Rademacher, A.; Märkle, S.; Langhals, H.; Chem. Ber. 1982,115,2927.

    Article  CAS  Google Scholar 

  27. Graser, F.; Hädicke, E.; Liebigs. Ann. Chem. 1980,1994; 1984,483.

    Google Scholar 

  28. Nagao, Y.; Misono, T.; Dyes Pigm. 1984,5,171.

    Article  CAS  Google Scholar 

  29. Quante, H.; Geerts, Y.; Müllen, K; Chem. Mater. 1997,9,495.

    Article  CAS  Google Scholar 

  30. Quante, H.; Doktor Arbeit, Mainz, 1995.

    Google Scholar 

  31. Geerts, Y.; Quante, H.; Platz, H.; Mahrt, R.; Hopmeier, M.; Böhm, A.; Müllen, K.; J. Mater, Chem., in press.

    Google Scholar 

  32. Holtrup, F.O.; Müller, G.R.J.; Quante, H.; De Feyter, S.; De Schryver, F.C.; Müllen, K.; Chem. Eur. J. 1997,3,219.

    Article  CAS  Google Scholar 

  33. Schlichting, P.; Rohr, U.; Müllen, K.; Liebigs Ann./Recueil 1997,395.

    Google Scholar 

  34. Dobowski, J.; Grabowski, Z.; Paeplow, B.; Rettig, W.; Koch, K.H.; Müllen, K.; New. J. Chem. 1994,18,525.

    Google Scholar 

  35. Anton, U.; Göltner, C.; Müllen, K.; Chem. Ber. 1992,125,2325.

    Article  CAS  Google Scholar 

  36. Schmidt, A.; Armstrong, N.R.; Göltner, C.; Müllen, K.; J. Phys. Chem. 1994,98,11780.

    Article  CAS  Google Scholar 

  37. Koch, K.H.; Müllen K.; Chem. Ber. 1991,124,2091.

    Article  CAS  Google Scholar 

  38. Müllen, K.; Scherf, U.; Makromol. Chem., Macromol. Symp. 1993,69,23.

    Article  Google Scholar 

  39. Fabian, J.; Nakazumi, H.; Matsuoka, M.; Chem. Rev. 1992,92,1197.

    Article  CAS  Google Scholar 

  40. Quante, H.; Müllen, K.; Angew. Chem. Int. Ed. Engl. 1995,34,1323.

    Article  CAS  Google Scholar 

  41. van de Craats, A.; Warman, J.; Müllen, K.; Geerts, Y.; Brandt, J.-D.; Adv. Mater. 1998,10,36.

    Article  Google Scholar 

  42. Cimrovà, V.; Remmers, M.; Neher, D.; Wegner, G.; Adv. Mater. 1996,8,146.

    Article  Google Scholar 

  43. Keller, U.; Müllen, K.; De Feyter, S.; De Schryver, F.C.; Adv. Mater. 1996,8,490 Keller, U.; Müllen, K.; Geerts, Y.; unpublished results.

    Article  CAS  Google Scholar 

  44. Grüner, J.; Wittmann, H.F.; Hamer, P.J.; Friend, R.H.; Huber, J.; Scherf, U.; Müllen, K.; Moratti, S.C.; Holmes, A.B.; Synth. Met. 1994,67,181.

    Article  Google Scholar 

  45. Göltner, C.; Pressner, D.; Müllen, K.; Spiess, H.W.; Angew. Chem. Int. Ed. Engl. 1993, 32, 1660 Pressner, D.; Göltner, C.; Spiess, H.W.; Müllen, K.; Ber. Bunsenges. Phys. Chem. 1993, 97, 1362.

    Article  Google Scholar 

  46. Müller, G.R.J.; Ph.D. Thesis, Mainz, 1996 Müller, G.R.J, Meiners, C.; Geerts, Y.; Enkelmann, V.; Müllen, K.; J. Mater. Chem. 1998,8,61.

    Google Scholar 

  47. Keller, U.; Doktor Arbeit, Mainz, 1996.

    Google Scholar 

  48. Gross, M.; Meerholz, K.; Brauchle, C.; Schlichting, P.; Rohr, U.; Müllen, K.; Angew. Chem. Int. Ed. Engl. 1998,37,1435.

    Google Scholar 

  49. Collings, P.J.; Hird, M.; Introduction to Liquid Crystals, Taylor and Francis, London, 1997.

    Book  Google Scholar 

  50. Biasutti, M.A.; De Feyter, S.; De Backer, S.; Dutt, G.B.; De Schryver, F.C.; Ameloot, M.; Schlichlting, P.; Müllen, K.; Chem. Phys. Lett. 1996,248,13.

    Article  CAS  Google Scholar 

  51. Geerts, Y.; Platz, H.; Quante, H.; Meiners, C.; Müllen, K.; unpublished results.

    Google Scholar 

  52. Herrmann, A.; Geerts, Y.; Keller, U.; Müllen, K.; unpublished results.

    Google Scholar 

  53. Hunter, A.C.; Sanders, J.K.M.; J. Am. Chem. Soc. 1990,112,5525 Williams, J.H.; Acc. Chem. Res. 1993,26,593.

    Article  CAS  Google Scholar 

  54. Herwig, P.; Kayser, C.W.; Müllen, K.; Spiess, H.W.; Adv. Mater. 1996,8,510.

    Article  CAS  Google Scholar 

  55. Biasutti, M.A.; Rommens, J.; Vaes, A.; De Feyter, S.; De Schryver, F.C.; Herwig, P.; Müllen, K.; Bull. Soc. Chim. Belg., in press.

    Google Scholar 

  56. Grimme, J.; Kreyenschmidt, Uckert, F.; Müllen, K.; Scherf, U.; Adv. Mater. 1995,7,292.

    Article  CAS  Google Scholar 

  57. Bohnen, A.; Koch K.-H.; Lüttke, W.; Müllen, K.; Angew. Chem. Int. Ed. Engl. 1990,29,525.

    Article  Google Scholar 

  58. De Backer, S.; Negri, M.R.; De Feyter, S.; Bhaskar Dutt, G.; Ameloot, M.; De Schryver, F.C.; Müllen, K.; Holtrup, F.; Chem. Phys. Lett. 1995,233,538.

    Article  Google Scholar 

  59. De Backer, S.; Bhaskar Dutt, G.; Ameloot, M.; De Schryver, F.C.; Müllen, K.; Holtrup, F.; J. Phys. Chem. 1996,100,512.

    Article  CAS  Google Scholar 

  60. Tittel, J.; Kettner, R.; Basché, Th.; Brauchle, C.; Quante, H.; Müllen, K.; J. Lumin. 1995, 64,1.

    Article  CAS  Google Scholar 

  61. Meyer, Y.H.; Plaza, P.; Müllen, K.; Chem. Phys. Lett. 1997,264,643.

    Article  CAS  Google Scholar 

  62. a) Meerholz, K.; Gregorius, H.; Müllen, K.; Heinze, J.; Adv. Mater. 1994,6,671. b) Schenk, R.; Gregorius, H.; Müllen, K.; Adv. Mater. 1991,10,492. c) Brendel, P.; Grupp. A.; Mehring, M.; Schenck, R.; Müllen, K.; Huber, W.; Synth. Met. 1991,45,49. d) Barth, S.; Bässler, H.; Wehrmeister, T.; Müllen, k.; J. Phys. Chem. 1997,106,321.

    Article  CAS  Google Scholar 

  63. a) Tian, B.; Zerbi, G.; Schenck, R.; Müllen, K.; J. Phys. Chem. 1991, 95, 3191. b) Tian, B.; Zerbi, G.; Schenck, R.; Müllen, K.; J. Phys. Chem. 1991,95,3198. c) Cornil, J.; Beljonne, D.; Shuai, Z.; Hagler, T.W.; Campbell, I.; Bradley, D.D.C; Brédas, J.L.; Sprangler, C.W.; Müllen, K.; Chem. Phys. Lett. 1995,247,425.

    Article  CAS  Google Scholar 

  64. Schenck, R.; Gregorius, H.; Meerholz, K.; Heinze, J.; Müllen, K.; J. Am. Chem. Soc. 1991, 113,2634.

    Article  Google Scholar 

  65. Mathy, A.; Ueberhofen, K.; Schenk, R.; Gregorius, H.; Garay, R.; Müllen, K.; Bubeck, C.; Phys. Rev. B 1996,53,4367.

    Article  CAS  Google Scholar 

  66. a) Borroughes, J.H.; Bradley, D.D.C.; Brown, A.R.; Marks, R.N.; Friend, R.H.; Burn, P.L.; Holmes, A.B.; Nature 1990, 347, 539. b) Hennecke, M.; Dammerau, T.; Müllen, K.; Macromolecules 1993,26,3411.

    Article  Google Scholar 

  67. Heller, C.M.; Campbell, I.H.; Laurich, B.K.; Smith, D.L.; Bradley, D.D.C.; Burn, P.L.; Ferraris, J.P.; Müllen, K.; Phys. Rev. B 1996,54,5516.

    Article  CAS  Google Scholar 

  68. Choong, V.; Park. Y.; Gao, Y.; Wehrmeister, T.; Müllen, K.; Hsieh, B.R.; Tang, C.W. Appl. Phys. Lett. 1996,69,1492.

    Article  CAS  Google Scholar 

  69. Grem, G.; Leising, G.; Synth. Met. 1993,55–57,4105.

    Article  Google Scholar 

  70. Grem, G.; Leditzky, G.; Ulrich, B.; Leising, G.; Adv. Mater. 1992,4,37.

    Article  Google Scholar 

  71. Grimme, J.; Scherf, U.; Macromol. Chem. Phys. 1996,197,2297.

    Article  CAS  Google Scholar 

  72. Pauck, T.; Bässler, H.; Grimme, J.; Scherf, U.; Müllen, K.; Chem. Phys. 1996,210,219.

    Article  CAS  Google Scholar 

  73. Kreyenschmidt, M.; Baumgarten, M; Tyutyulkov, N.; Müllen, K.; Angew. Chem. Int. Ed. Engl. 1994,33,1957.

    Article  Google Scholar 

  74. Kreyenschmidt, M.; Ph.D. Thesis, Mainz, 1996.

    Google Scholar 

  75. Keegstra, M.A.; De Feyter, S.; De Schryver, Müllen, K.; Angew. Chem. Int. Ed. Engl. 1996,35,774.

    Article  CAS  Google Scholar 

  76. Nishiyama, K.; Honda, T.; Okada, T.; Reis, H.; Baumann, W.; Müller, U.; Müllen, K.; J. Phys. Chem. 1998,102,2936.

    Google Scholar 

  77. a) Schlüter, A.D.; Wegner, G.; Acta Polymer. 1993,44,59. b) Tour, J.M.; Adv. Mater. 1994,6, 190. c) Kovacic, P.; Jones, M.B.; Chem. Rev. 1987,87,357.

    Article  Google Scholar 

  78. a) Friend, R.H.; Denton, G.J.; Halls, J.J.M.; Harisson, N.T.; Holmes, A.B.; Köhler, A.; Lux, A.; Moratti, S.C.; Pichler, K.; Tessler, N.; Towns, K.; Wittmann, H.F.; Solid State Comm. 1997, 102, 249. b) Rothberg, L.J.; Yan, M.; Papadimitrakopoulos, F.; Galvin, M.E.; Kwock, E.W.; Miller, T.M.; Synth. Met. 1996, 80, 41. c) Obrzut, J.; Karasz, F.E.; J. Chem. Phys. 1987, 87, 2349.

    Article  CAS  Google Scholar 

  79. Pope, M.; Kallmann, H.; Magnante, P.; J. Chem. Phys. 1963,38,2042.

    Article  CAS  Google Scholar 

  80. Weiss, K.; Michel, A.; Auth, E.M.; Bunz, U.H.F.; Mangel, T.; Müllen, K.; Angew. Chem. Int. Ed. Engl. 1997,36,506.

    Article  CAS  Google Scholar 

  81. Bunz, U.; Francke, V.; Klapper, M.; Uckert, F.; Müllen, K.; Polymer Synthesis with Organometallic Intermediates In Proceedings of the Fifth Symposium on Organic Synthesis via Organometallics in Heidelberg, Friedr. Vieweg & Sohn, Braunschweig/ Wiesbaden, 1997.

    Google Scholar 

  82. Garay, R.O.; Baier, U.; Bubeck, C.; Müllen, K.; Adv. Mater. 1993,5,561.

    Article  CAS  Google Scholar 

  83. Mangel. T.; Eberhardt, A.; Scherf, U.; Bunz, U.H.F.; Müllen, K.; Macromol. Rapid Commun. 1995,16,571 Weiss, K.; Michel, A.; Auth, E.M.; Bunz, U.H.F.; Mangel, T.; Müllen, K.; Angew. Chem. Int. Ed. Engl. 1997,36,506.

    Article  CAS  Google Scholar 

  84. Klärner, G.; Former, C.; Martin, K.; Rader, J.; Müllen, K.; Macromolecules, 1998,31,3571.

    Article  Google Scholar 

  85. Staring, E.G.; Demandt, R.C.; Braun, D.; Rikken, G.L.; Kessener, Y.A.; Venhuizen, T.H.; Wynberg, H.; ten Hoeve, W.; Spoeltra, K.J.; Adv. Mater. 1994,6,935.

    Article  Google Scholar 

  86. Sonoda, Y.; Kaeriyama, K.; Bull. Chem. Soc. Jpn. 1992,65,853.

    Article  CAS  Google Scholar 

  87. Huber, J.; Scherf, U.; Macromol. Rapid Commun. 1994,15,897.

    Article  CAS  Google Scholar 

  88. Mahrt, R.F.; Pauck, T.; Lemmer, U.; Siegner, U.; Hopmeier, R.; Hennig, R.; Bässler, H.; Göbel, E.O.; Haring Bolivar, P.; Wegmann, G.; Kurz, H.; Scherf, U.; Müllen, K.; Phys. Rev. B. 1996,54,1759.

    Article  CAS  Google Scholar 

  89. Pauck, T.; Hennig, R.; Perner, M.; Lemmer, U.; Siegner, U.; Mahrt, R.F.; Scherf, U.; Müllen, K.; Bässler, H.; Göbel, E.O.; Chem. Phys. Lett. 1995,244,171.

    Article  CAS  Google Scholar 

  90. Scherf, U.; Müllen, K.; Adv. Polym. Sci. 1995,123,1.

    Article  CAS  Google Scholar 

  91. Chmil, K.; Scherf, U.; Acta Polymer. 1997,48,208 Chmil, K.; Scherf, U.; Makromol. Chem., Rapid Commun. 1993,14,217.

    Article  CAS  Google Scholar 

  92. Kreyenschmidt, M.; Uckert, F.; Müllen, K.; Macromolecules 1995,28,4577.

    Article  CAS  Google Scholar 

  93. Christie, R.M.; Polym. Int. 1994,34,351.

    Article  CAS  Google Scholar 

  94. Beck, K.H.; Etzbach, K.-H.; Schmidt, H.-W. EP 0 422 535A1, 1990. Etzbach, K.-H; Beck, K.H.; Wagenblast, G. EP 0 422 538A1,1990.

    Google Scholar 

  95. Feiler, L.; Langhals, H.; Polborn, K.; Liebigs Ann. 1995,1229.

    Google Scholar 

  96. Holtrup, F.O.; Müller, G.R.J.; Uebe, J.; Müllen, K.; Tetrahedron, 1997,53,6847.

    Article  CAS  Google Scholar 

  97. Schmidt, A.; Anderson, M.L.; Dunphy, D.; Wehrmeister, T.; Müllen, K.; Adv. Mater. 1995,7, 722.

    Article  CAS  Google Scholar 

  98. Scherf, U.; Müllen, K.; Makromol. Chem., Rapid Commun. 1991,12,489.

    Article  CAS  Google Scholar 

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Geerts, Y., Müllen, K. (1999). Advanced Light Emitting Dyes: Monomers, Oligomers, and Polymers. In: Applied Fluorescence in Chemistry, Biology and Medicine. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-59903-3_13

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