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III.2.17.2 SYNTHESIS OF CONJUGATED POLYMERS FOR MATERIALS SCIENCE

855

 

 

 

 

 

 

 

R

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

TfO

 

 

 

 

OTf

 

+ Me3Sn

 

 

 

 

SnMe3

 

 

 

R

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

R = (CH2)nCH3, n = 5, 7, 11

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

R = (CH2)10CO2C2H5

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

84

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

Tf = SO2CF3

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

n

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

R

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

R

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

O

 

 

O

 

 

 

 

 

 

 

 

 

 

 

 

 

 

O

O

 

 

O

 

 

O

 

 

 

 

 

 

 

 

 

 

 

 

 

 

O

O

85

 

 

 

 

 

 

 

 

SnBu3

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

+

Bu3Sn

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

S

 

 

S

 

 

 

 

 

 

 

 

 

 

 

 

 

 

S

S

 

I

 

 

 

 

I

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

R = calix[4]arene

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

n

 

O

R

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

O

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

O

 

 

 

O

 

Me3Sn

 

 

 

 

 

SnMe3

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

+

 

S

S

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

S

 

 

S

 

 

R

R

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

I

 

 

 

 

I

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

R

 

 

O

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

O

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

O

 

 

O

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

86

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

S

 

S

 

 

 

S

 

 

S

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

n

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

R

 

 

R

 

 

 

 

 

R

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

R

 

 

 

 

 

 

 

 

 

 

 

 

O

 

+

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

O

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

Br

 

 

 

 

Br

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

Bu3Sn

S

SnBu3

 

 

 

 

 

 

 

 

 

 

 

 

S

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

O

 

R

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

O

 

 

R

 

 

 

n

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

87

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

R = -1,4-C6H4-C10H21

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

Chart III (Continued)

856

III Pd-CATALYZED CROSS-COUPLING

Chart IV

III.2.17.2 SYNTHESIS OF CONJUGATED POLYMERS FOR MATERIALS SCIENCE

857

D. OUTLOOK

In a little over ten years the area of conjugated polymers with all-hydrocarbon backbones has been revolutionized. Previously “nonexistent” polymers like poly(arylene)s, poly(arylene vinylene)s, and poly(arylene ethinylene)s were made available with a broad variety of substitution patterns. This decoration with substituents not only made them soluble and processible but also mediated function. Though there are still some synthetic hurdles to be overcome, the future of Pd-mediated syntheses of polymers looks bright. The ever increasing demand for conjugated polymers will nourish chemists’ creativity and involvement to overcome these hindrances and to design new polymer structures. The costs for the polymers synthesized via the Pd-mediated step-growth procedures reported here are high. Apart from commodity polymers, however, this does not discourage their application. Only very small amounts are needed and the price of a device does not really depend on the costs of its organic active component. A good example for this is polymer 21, which is already commercially produced. One final comment from a chemist who sees the chemical world from the vantage point of synthesis: many, many step-known growth polymerizations found huge markets. All of them connect monomers via carbon hetero bonds, mostly CO or CN, none of them via C—C single bonds. This is what makes the polymerizations described here so special. Ten years from now a few more of them will have made it to technical production.

REFERENCES

[1]A. Suzuki, Pure Appl. Chem., 1994, 66, 213.

[2]N. Miyaura and A. Suzuki, Chem. Rev., 1995, 95, 2457.

[3]R. F. Heck, Pallaudium Reagents in Organic Synthesis, Academic. Press, London, 1985, pp. 1.

[4]J. K. Stille, Angew. Chem. Int. Ed. Engl., 1986, 25, 508.

[5]K. Sonogashira, Y. Thoda, and N. Hagihara, Tetrahedron Lett., 1975, 4467.

[6]Y. Thoda, K. Sonogashira, and N. Hagihara, Synthesis, 1977, 777.

[7]R. A. Weßling and R. G. Zimmermann (Dow Chemical), US-B 3 401 152, 1968 [Chem. Abstr., 1968, 69, 87735q].

[8]R. A. Weßling, J. Polym. Sci. Polym. Symp., 1985, 72, 55.

[9]R. W. Lenz, C.-C. Han, J. Stenger-Smith, and F. E. Karasz, J. Polym. Sci. Polym. Chem. Ed., 1988, 26, 3241.

[10]P. L. Burn, D. D. C. Bradley, R. H. Friend, D. A. Halliday, A. B. Holmes, R. W. Jackson, and A. Kraft, J. Chem. Soc. Perkin Trans. 1, 1992, 3225.

[11]T. A. Skotheim, R. L. Elsenbaumer, and J. R: Reynolds, Eds., Handbook of Conducting Polymers, Marcel Dekker, New York, 1998, pp. 209.

[12]J. M. Tour, Chem. Rev., 1996, 96, 537 – 553.

[13]A. J. Berresheim, M. Müller, and K. Müllen, Chem. Rev., 1999, 99, 1747 – 1785

[14]T. Kanbara, A. Honma, and K. Hasegawa, Chem. Lett., 1996, 1135.

[15]F. E. Goodson and J. F. Hartwig, Macromolecules, 1998, 31, 1700.

[16]T. A. Skotheim, R. L. Elsenbaumer, and J. R. Reynolds, Eds., Handbook of Conducting Polymers, Marcel Dekker, New York, 1998, Chap. II.8, 209 – 224.

[17] W. Heitz, in Synthesis of Polymers, A. D. Schlüter, Ed., pp. 38 – 61 in the series “Materials Science and Technology”, Wiley-VCH, Weinheim, 1999.

858III Pd-CATALYZED CROSS-COUPLING

[18]A. D. Schlüter, Acta Polymer, 1993, 44, 59.

[19]J. M. G. Cowie, Polymers: Chemistry and Physics of Modern Materials, International Textbook Comp., Aylesbury, 1973.

[20]Z. Bo and A. D. Schlüter, Chem Eur. J., 2000, 6, 3235.

[21]K. Matos and J. A. Soderquist, J. Org. Chem., 1998, 63, 461.

[22]J. Frahn, B. Karakaya, A. Scha¨fer, and A. D. Schlüter, Tetrahedron, 1997, 53, 15459.

[23]D. Matteson and D. Majumdar, J. Am. Chem. Soc., 1980, 102, 7588.

[24]S. Schlüter, J. Frahn, B. Karakaya, and A. D. Schlüter, Macromol. Chem. Phys., 2000, 201, 139.

[25] C.-S. Wang, M. Kilitziraki, J. A. H. MacBride, M. R. Bryce, L. E. Horsburgh,

A.K. Sheridan, A. P. Monkman, and I. D. W. Samuel, Adv. Mater., 2000, 12, 217.

[26]H. Gröger, J. Prakt. Chem., 2000, 342, 334.

[27]S. Gronowitz and D. Peters, Heterocycles, 1990, 30, 645.

[28]M. Ballauff, Angew. Chem. Int. Ed. Engl., 1989, 28, 253.

[29]H. O. Wirth, in Physik und Chemie der Scintillatoren, N. Riehl and H. P. Kallmann, Eds.,

K.Thieme Verlag, München, 1966.

[30]N. Miyaura, T. Yanagi, and A. Suzuki, Synth. Commun., 1981, 11, 513.

[31]T. I. Wallow and B. M. Novak, J. Am. Chem. Soc., 1991, 113, 7411.

[32]M. Rehahn, A. D. Schlüter, G. Wegner, and W. J. Feast, Polymer, 1989, 30, 1054.

[33]M. Rehahn, A. D. Schlüter, G. Wegner, and W. J. Feast, Polymer, 1989, 30, 1060.

[34]M. Rehahn, A. D. Schlüter, and G. Wegner, Makromol. Chem., 1990, 191, 1991.

[35]U. Fahnenstich, K.-H. Koch, and K. Müllen, Makromol. Chem. Rapid Commun., 1989, 10, 563.

[36]I. U. Rau and M. Rehahn, Makromol. Chem., 1993, 194, 2225.

[37]T. Vahlenkamp and G. Wegner, Macromol. Chem. Phys., 1994, 195, 1933.

[38]J. Huber and U. Scherf, Macromol. Rapid Commun., 1994, 15, 879.

[39]M. Remmers, M. Schulze, and G. Wegner, Macromol. Rapid Commun., 1996, 17, 239.

[40]J. Grüner, M. Remmers, and D. Neher, Adv. Mater., 1997, 9, 964.

[41]B. Karakaya, W. Claussen, A. Scha¨fer, A. Lehmann, and A. D. Schlüter, Acta Polymer., 1996, 47, 79.

[42]N. Tanigaki, H. Masuda, and K. Kaeriyama, Polymer, 1997, 38, 1221.

[43]S. Brunner, W. R. Caseri, U. W. Suter, G. Ha¨hner, D. Brovelli, N. D. Spencer, A. Vinckier,

I.U. Rau, P. Galda, and M. Rehahn, Langmuir, 1999, 15 , 6333.

[44]J. Frahn, B. Karakaya, A. Scha¨fer, and A. D. Schlüter, Tetrahedron, 1997, 53, 15459.

[45]C. Kowitz and G. Wegner, Tetrahedron, 1997, 53, 15553.

[46]R. Fiesel, and U. Scherf, Acta Polym., 1998, 49, 445.

[47]Y. Miura, H. Oka, and M. Morita, Macromolecules, 1998, 31, 2041.

[48]W.-L. Yu, J. Pei, Y. Cao, W. Huang, and A. J. Heeger, Chem. Commun., 1999, 1837.

[49]M. Bernius, M. Inbasekaran, E. Woo, W. Wu, and L. Wujkowski, Thin Solid Films, 2000, 363, 55.

[50]M. Remmers, B. Müller, K. Martin, H. J. Ra¨der, and W. Köhler, Macromolecules, 1999, 32, 1073.

[51]A. Kraft, A. C. Grimbsdale, and A. B. Holmes, Angew. Chem. Int. Ed. Engl., 1998, 37, 402.

[52]R. H. Friend, R. W. Gymer, A. B. Holmes, J. H. Burroughes, R. N. Marks, C. Taliani,

D.D. C. Bradley, D. A. Dos Santos, J. L. Brédas, M. Lögdlund, and W. R. Salanek, Nature, 1999, 397, 121.

[53]G. Grem, G. Leditzky, B. Ullrich, and G. Leising, Adv. Mater., 1992, 4, 36.

III.2.17.2 SYNTHESIS OF CONJUGATED POLYMERS FOR MATERIALS SCIENCE

859

[54]F. Helmer-Metzmann, M. Rehahn, L. Schmitz, M. Ballauff, and G. Wegner, Makromol. Chem., 1992, 193, 1847.

[55]L. Schmitz, M. Rehahn, and M. Ballauff, Polymer, 1993, 34, 646.

[56]U. Lauter, W. H. Meyer, and G. Wegner, Macromolecules, 1997, 30, 2092.

[57]U. Lauter, W. H. Meyer, V. Enkelmann, and G. Wegner, Macromol. Chem. Phys., 1998, 2129.

[58]C. Zhang and A. D. Schlüter, unpublished results.

[59]Z. S. Bo, C. M. Zhang, N. Severin, J. P. Rabe, and A. D. Schlüter, Macromolecules, 2000, 33, 2688.

[60]Z. S. Bo, J. P. Rabe, and A. D. Schlüter, Angew. Chem. Int. Ed. Engl., 1999, 38, 2370.

[61]R. Rulkens, M. Schulze, and G. Wegner, Macromol. Rapid Commun., 1994, 15, 669.

[62]R. Rulkens, G. Wegner, V. Enkelmann, and M. Schulze, Ber. Bunsenges. Phys. Chem., 1996, 100, 707.

[63]V. Cimrova, W. Schmidt, R. Rulkens, M. Schulze, W. Meyer, and D. Neher, Adv. Mater., 1996, 8, 585.

[64] S. Vanhee, R. Rulkens, U. Lehmann, C. Rosenauer, M. Schulze, W. Köhler, and

G.Wegner, Macromolecules, 1996, 29, 5136.

[65]T. Liu, R. Rulkens, G. Wegner, and B. Chu, Macromolecules, 1998, 31, 6119.

[66]M. Bockstaller, W. Köhler, G. Wegner, D. Vlassopoulos, and G. Fytas, Macromolecules, 2000, 38, 3952.

[67]I. U. Rau and M. Rehahn, Acta Polym., 1994, 45, 3.

[68]S. Kim, J. Jackiw, E. Robinson, K. S. Schanze, J. R. Reynolds, J. Baur, M. F. Rubner, and

D.Boils, Macromolecules, 1998, 31, 964.

[69]J. W. Baur, S. Kim, P. B. Balanda, J. R. Reynolds, and M. F. Rubner, Adv. Mater., 1998, 10, 1452.

[70]P. B. Balanda, M. B. Ramey, and J. R. Reynolds, Macromolecules, 1999, 32, 3970.

[71]M. Wittemann and M. Rehahn, Chem. Commun., 1998, 623.

[72]A. F. Thünemann, D. Ruppelt, H. Schnablegger, and Jürgen Blaul, Macromolecules, 2000, 33, 2124.

[73]A. D. Schlüter, Adv. Mater., 1991, 3, 282.

[74]A. D. Schlüter, in Desk Reference of Functional Polymers, Synthesis and Applications,

R.Arshady, Ed., ACS Books, Washington, DC, 1996, 73 – 88.

[75]U. Scherf and K. Müllen, Makromol. Chem. Rapid Commun., 1991, 12, 489.

[76]U. Scherf and K. Müllen, Polymer Commun., 1992, 33, 2443.

[77]U. Scherf and K. Müllen, Macromolecules, 1992, 25, 3546.

[78]J. Stampfl, W. Graupner, G. Leising, and U. Scherf, J. Luminescence, 1995, 63, 117.

[79]A. Köhler, J. Grüner, R. H. Friend, K. Müllen, and U. Scherf, Chem. Phys. Lett., 1995, 243, 456

[80]W. Graupner, G. Leising, G. Lanzani, M. Nisoli, S. De Silvestri, and U. Scherf, Chem. Phys. Lett., 1996, 246, 95.

[81]C. Zenz, W. Graupner, S. Tasch, G. Leising, K. Müllen, and U. Scherf, Appl. Phys. Lett., 1997, 71, 2566.

[82]C. Kallinger, M. Hilmer, A. Haugenender, M. Perner, W. Spirkl, U. Lemmer, J. Feldmann,

U.Scherf, K. Müllen, A. Gombert, and V. Wittner, Adv. Mater., 1998, 10, 920.

[83]J. M. Tour and J. J. S. Lamba, J. Am. Chem. Soc., 1993, 115, 4935.

[84]J. J. S. Lamba and J. M. Tour, J. Am. Chem. Soc., 1994, 116, 11723.

[85]M. B. Goldfinger, K. B. Crawfold, and T. M. Swager, J. Am. Chem. Soc., 1997, 119, 4578.

860III Pd-CATALYZED CROSS-COUPLING

[86]M. B. Goldfinger, K. B. Crawfold, and T. M. Swager, J. Org. Chem., 1998, 63, 1676.

[87]A. Haryono, K. Miyatake, J. Natori, and E. Tsuchida, Macromolecules, 1999, 32, 3146.

[88]J. Huber, K. Müllen, J. Salbeck, U. Scherf, T. Stehlin, and R. Stern, Acta Polym., 1994, 45, 244.

[89]Q. S. Hu, D. Vitharana, G. Y. Liu, V. Jain, M. W. Wagaman, L. Zhang, T. R. Lee, and

L.Pu, Macromolecules, 1996, 29, 1082.

[90]Q. S. Hu, D. Vitharana, G. Liu, V. Jain, and L. Pu, Macromolecules, 1996, 29, 5075.

[91]W.-S. Huang, Q.-S. Hu, X.-F. Zheng, J. Anderson, and L. Pu, J. Am. Chem. Soc., 1997, 119, 4313.

[92]Q.-S. Hu, W.-S. Huang, and L. Pu, J. Org. Chem., 1998, 63, 2798.

[93]M. Johannsen, K. A. Jorgensen, X.-F. Zheng, Q.-S. Hu, and L. Pu, J. Org. Chem., 1999, 64, 299.

[94]W.-S. Huang, Q.-S. Hu, and L. Pu, J. Org. Chem., 1999, 64, 7940.

[95]H.-B. Yu, X.-F. Zheng, Z.-M. Lin, Q.-S. Hu, W.-S. Huang, and L. Pu, J. Org. Chem., 1999, 64, 8149.

[96]L. Pu, Macromol. Chem. Phys., 2000, 21, 795.

[97]B. Karakaya, W. Claussen, K. Gessler, W. Saenger, and A. D. Schlüter, J. Am. Chem. Soc., 1997, 119, 3296.

[98]W. Stocker, B. Karakaya, B. L. Schürmann, J. P. Rabe, and A. D. Schlüter, J. Am. Chem. Soc., 1998, 120, 7691.

[99]Z. S. Bo and A. D. Schlüter, Macromol. Rapid Commun., 1999, 20, 21.

[100]A. D. Schlüter and J. P. Rabe, Angew. Chem. Int. Ed. Engl., 2000, 39, 864.

[101]F. Koch and W. Heitz, Macromol. Chem. Phys., 1997, 198, 1531.

[102]M. Rehahn, A. D. Schlüter, and G. Wegner, Makromol. Chem. Rapid Commun., 1990, 11, 535.

[103]Y. H. Kim and O. W. Webster, J. Am. Chem. Soc., 1990, 112, 4592.

[104]Y. H. Kim and O. W. Webster, Macromolecules, 1992, 25, 5561.

[105]S. Martina and A. D. Schlüter, Macromolecules, 1992, 25, 3607.

[106]F. E. Goodson and B. M. Novak, Macromolecules, 1997, 30, 6047.

[107]K. K. Anderson and D. A. Dougherty, Adv. Mater., 1998, 10, 688.

[108]S. Förster, I. Neubert, A. D. Schlüter, and P. Lindner, Macromolecules, 1999, 32, 4043.

[109]F. Goodson, T. I. Wallow, and B. M. Novak, Macromolecules, 1998, 31, 2047.

[110]B. M. Novak, T. I. Wallow, F. Goodson, and K. Loos, Am. Chem. Soc. Polym. Chem. Div. Polym. Prepr., 1995, 36(1), 693.

[111]D. Steiger, M. Ehrenstein, C. Weder, and P. Smith, Macromolecules, 1998, 31, 1254.

[112]S. Klingelhöfer, C. Schellenberg, J. Pommerehne, H. Ba¨ssler, A. Greiner, and W. Heitz,

Macromol. Chem. Phys., 1997, 198, 1511.

[113]W. Heitz, Pure Appl. Chem., 1995, 67, 1951.

[114]M. J. Marsella, D.-K. Fu, and T. M. Swager, Adv. Mater., 1995, 7, 145.

[115]Z. N. Bao, Y. M. Chen, and L. P. Yu, Macromolecules, 1994, 27, 4629.

[116]Q. Wang, L. Wang, and L. Yu, Macromol. Rapid Commun., 2000, 21, 723.

[117]A. Greiner and W. Heitz, Makromol. Chem. Rapid Commun., 1988, 9, 581.

[118]W. Heitz, W. Brügging, L. Freund, M. Gailberger, A. Greiner, H. Jung, U. Kampschulte,

N.Nießner, F. Osan, H.-W. Schmidt, and W. Wicker, Makromol. Chem., 1988, 189, 119.

[119]M. Benda, A. Greiner, and W. Heitz, Makromol. Chem., 1990, 191, 1983.

[120]H.-P. Weitzel and K. Müllen, Makromol. Chem., 1990, 191, 2837.

[121]H. Martelock, A. Greiner, and W. Heitz, Makromol. Chem., 1991, 191, 967.

III.2.17.2 SYNTHESIS OF CONJUGATED POLYMERS FOR MATERIALS SCIENCE

861

[122]Y. Imai, Makromol. Chem. Macromol. Symp., 1992, 54/55, 151.

[123]Z. Bao, Y. Chen, R. Cai, and L. Yu, Macromolecules, 1993, 26, 5281.

[124]Z. Peng, A. R. Gharavi, and L. Yu, J. Am. Chem. Soc., 1997, 119, 4622.

[125]Q. Wang, L. Wang, and L. P. Yu, J. Am. Chem. Soc., 1998, 120, 12860.

[126]R. Galarini, A. Musco, R. Pontellini, A. Bolognesi, S. Destri, M. Catellani, M. Mascherpa, and G. Zhuo, J. Chem. Soc. Chem. Commun., 1991, 364.

[127]X. Qian and M. Pena, Macromolecules, 1995, 28, 4415.

[128]M. J. Marsella, R. J. Newland, P. J. Carroll, and T. M. Swager, J. Am. Chem. Soc., 1995, 117, 9842.

[129]M. Forster, K. O. Annan, and U. Scherf, Macromolecules, 1999, 32, 3159.

[130]J. M. Parraka, A. P. Chacko, D. E. Nikles, P. Wang, S. Hasegawa, Y. Maruyama, R. M. Metzger, and M. P. Cava, Macromolecules, 1996, 29, 1928.

[131]R. Gisa and R. C. Schulz, Makromol. Chem., 1990, 191, 857.

[132]V. A. Solomin and W. Heitz, Macromol. Chem. Phys., 1994, 195, 303.

[133]H. Ha¨ger and W. Heitz, Macromol. Chem. Phys., 1998, 199, 1821.

[134]K. Sanechika, T. Yamamoto, and A. Yamamoto, Bull. Chem. Soc. Jpn., 1984, 57, 752.

[135]S. J. Havens and P. M. Hergenrother, J. Polym. Sci. Polym. Lett. Ed., 1985, 23, 587.

[136]D. L. Trumbo and C. S. Marvel, J. Polym. Sci. Polym. Chem. Ed., 1986, 24, 2311.

[137]C. Pugh and V. Percec, J. Polym. Sci. Polym. Chem. Ed., 1990, 28, 1101.

[138]M. Maroni, J. Le Moigne, and S. Luzzati, Macromolecules, 1994, 27, 562.

[139]T. M. Swager, C. J. Gil, and M. S. Wrighton, J. Phys. Chem., 1995, 99, 4886.

[140]D. Ofer, T. M. Swager, and M. S. Wrighton, Chem Mater., 1995, 7, 418.

[141]M. Altmann and U. H. F. Bunz, Angew. Chem. Int. Ed. Engl., 1995, 34, 569.

[142]T. Mangel, A. Eberhardt, U. Scherf, U. H. F. Bunz, and K. Müllen, Macromol. Rapid Commun., 1995, 16, 571.

[143]Q. Zhou and T. M. Swager, J. Am. Chem. Soc., 1996, 117, 12593.

[144]L. Ma, Q.-S. Hu, K. Y. Musick, D. Vitharana, C. Wu, C. M. S. Kwan, and L. Pu,

Macromolecules, 1996, 29, 5083.

[145]C. Weder and M. S. Wrighton, Macromolecules, 1996, 29, 5157.

[146]A. M. Weiss, E.-M. Auth, U. H. F. Bunz, T. Mangel, and K. Müllen, Angew. Chem. Int. Ed. Engl., 1997, 36, 506.

[147]K. D. Ley, C. E. Whittle, M. D. Bartberger, and K. S. Schanze, J. Am. Chem. Soc., 1997, 119, 3423.

[148]D. Steiger, P. Smith, and C. Weder, Macromol. Rapid Commun., 1997, 18, 643.

[149]C. Weder, C. Sarwa, A. Montali, C. Bastiaansen, and P. Smith, Science, 1998, 279, 835.

[150]H. Li, D. R. Powell, R. K. Hayashi, and R. West, Macromolecules, 1998, 31, 52.

[151]V. Francke, H. J. Ra¨der, Y. Geerts, and K. Müllen, Macromol. Rapid Commun., 1998, 19, 275.

[152]V. Francke, T. Mangel, and K. Müllen, Macromolecules, 1998, 31, 2447.

[153]C. E. Halkyard, M. E. Rampey, L. Kloppenburg, S. L. Studer-Martinez, and U. H. F. Bunz,

Macromolecules, 1998, 31, 8655.

[154]R. Fiesel and U. Scherf, Macromol. Rapid Commun., 1998, 19, 427.

[155]H. L. Douglas, R. Powell, R. K. Hayashi, and R. West, Macromolecules, 1998, 31, 52.

[156]S. Dellsperger, F. Dötz, P. Smith, and C. Weder, Macromol. Chem. Phys., 2000, 201, 192.

[157]L. S. Swanson, F. Lu, J. Shinar, Y. W. Ding, and T. J. Barton, Synth. Met., 1993, 55 – 57, 1.

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