Monodisperse poly(triacetylene) oligomers extending from monomer to hexadecamer: Joint experimental and theoretical investigation of physical properties

Chemistry - A European Journal

Volumn 6, Issue 19, 2000, Pages 3622-3635

  Martin, Rainer E ^a   Gubler, Ulrich ^a   Cornil, Jérôme ^b   Balakina, Marina ^b   Boudon, Corinne ^c   Bosshard, Christian ^a   Gisselbrecht, Jean Paul ^c   Diederich, François ^a   Günter, Peter ^a   Gross, Maurice ^c   Brédas, Jean Luc ^b,d  

^a ETH ZURICH   (Switzerland)

^b UNIVERSITY OF MONS   (Belgium)

^c UNIVERSITÉ DE STRASBOURG   (France)

^d University of Arizona   (United States)

Author keywords

Alkynes; Conjugation; Molecular wires; Nonlinear optics; Oligomers

Indexed keywords

ACETYLENE DERIVATIVE; OLIGOMER;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL ANALYSIS; CONJUGATION; CYCLIC POTENTIOMETRY; IONIZATION; OLIGOMERIZATION; OXIDATION REDUCTION POTENTIAL; PHYSICAL CHEMISTRY; SOLUBILITY;

EID: 0034596921     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3765(20001002)6:19<3622::AID-CHEM3622>3.0.CO;2-L     Document Type: Article

References (96)

1. a) A. Rajca, Chem. Rev. 1994, 94, 871-893;
2. b) J. S. Miller, A. J. Epstein, Angew. Chem. 1994, 106, 399-432; Angew. Chem. Int. Ed. Engl. 1994, 33, 385-415;
3. b) J. S. Miller, A. J. Epstein, Angew. Chem. 1994, 106, 399-432; Angew. Chem. Int. Ed. Engl. 1994, 33, 385-415;
4. c) J. S. Miller, Adv. Mater. 1992, 4, 435-438.
5. a) Handbook of Conducting Polymers (Eds.: T. A. Skotheim, R. L. Elsenbaumer, J. R. Reynolds), 2nd ed., Marcel Dekker, New York 1998;
6. b) Handbook of Organic Conductive Molecules and Polymers, Vol. 1-4 (Ed.: H. S. Nalwa), Wiley, Chichester, 1997.
7. a) F. Cacialli, Curr. Opin. Coll. Int. Sci. 1999, 4, 159-164;
8. b) 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, W. R. Salaneck, Nature 1999, 397, 121-128;
9. c) A. Kraft, A. C. Grimsdale, A. B. Holmes, Angew. Chem. 1998, 110, 416-443; Angew. Chem. Int. Ed. 1998, 37, 402-428;
10. c) A. Kraft, A. C. Grimsdale, A. B. Holmes, Angew. Chem. 1998, 110, 416-443; Angew. Chem. Int. Ed. 1998, 37, 402-428;
11. d) J. L. Segura, Acta Polym. 1998, 49, 319-344.
12. a) M. Granström, K. Petritsch, A. C. Arias, A. Lux, M. R. Andersson, R. H. Friend, Nature 1998, 395, 257-260;
13. b) K. Tada, M. Onoda, A. A. Zakhidov, K. Yoshino, Jpn. J. Appl. Phys. Pt2-Lett. 1997, 36, L306-L309;
14. c) K. Takahashi, S. Nakatani, T. Yamaguchi, T. Komura, S. Ito, K. Murata, Solar Energy Mater. Solar Cells 1997, 45, 127-139;
15. d) K. Yoshino, K. Tada, A. Fujii, E. M. Conwell, A. A. Zakhidov, IEEE Trans. Electron. Devices 1997, 44, 1315-1324;
16. e) G. Yu, A. J. Heeger, J. Appl. Phys. 1995, 78, 4510-4515;
17. f) J. J. M. Halls, C. A. Walsh, N. C. Greenham, E. A. Marseglia, R. H. Friend, S. C. Moratti, Nature 1995, 376, 498-500.
18. a) G. Horowitz, Adv. Mater. 1998, 10, 365-377;
19. b) H. E. Katz, J. G. Laquindanum, A. J. Lovinger, Chem. Mater. 1998, 10, 633-638;
20. c) T. Siegrist, C. Kloc, R. A. Laudise, H. E. Katz, R. C. Haddon, Adv. Mater. 1998, 10, 379-382;
21. d) G. Barbarella, P. Ostoja, P. Maccagnani, O. Pudova, L. Antolini, D. Casarini, A. Bongini, Chem. Mater. 1998, 10, 3683-3689;
22. e) H. Sirringhaus, R. H. Friend, X. C. Li, S. C. Moratti, A. B. Holmes, N. Feeder, Appl. Phys. Lett. 1997, 71, 3871-3873;
23. f) R. Hajlaoui, D. Fichou, G. Horowitz, B. Nessakh, M. Constant, F. Gamier, Adv. Mater. 1997, 9, 557-561:
24. g) D. Fichou, M.-P. Teulade-Fichou, G. Horowitz, F. Demanze, Adv. Mater. 1997, 9, 75-80.
25. a) R. R. Tykwinski, U Gubler, R. E. Martin, F. Diederich, C. Bosshard, P. Günter, J. Phys. Chem. B 1998, 102, 4451-4465;
26. b) J. L. Brédas, C. Adant, P. Tackx, A. Persoons, B. M. Pierce, Chem. Rev. 1994, 94, 243-278;
27. c) H. S. Nalwa in Nonlinear Optics of Organic Molecules and Polymers (Eds.: H. S. Nalwa, S. Miyata), CRC Press, New York, 1997, pp. 611-798;
28. d) S. R. Marder, B. Kippelen, A. K.-Y. Jen, N. Peyghambarian, Nature 1997, 388, 845-851;
29. e) A. J. Heeger, J. Long, Jr., Optics & Photonics News 1996, 7, 24-30;
30. f) For a recent overview on functional organic materials for electronic and optoelectronic devices, see special issues: J. Mater. Chem. 1999, 9, 1853-2276 and Acc. Chem. Res. 1999, 32, 191-276.
31. f) For a recent overview on functional organic materials for electronic and optoelectronic devices, see special issues: J. Mater. Chem. 1999, 9, 1853-2276 and Acc. Chem. Res. 1999, 32, 191-276.
32. R. H. Friend, J. Burroughes, T. Shimoda, Physics World 1999, 12, 35-40.
33. Electronic Materials: The Oligomer Approach (Eds.: K. Müllen, G. Wegner), WILEY-VCH, Weinheim, 1997.
34. a) J. Roncali, Chem. Rev. 1997, 97, 173-205;
35. b) J. M. Tour, Chem. Rev. 1996, 96, 537-553.
36. a) D. Bloor in Introduction to Molecular Electronics (Eds.: M. C. Petty, M. R. Bryce, D. Bloor), Edward Arnold, London, 1995, pp. 1-28;
37. b) For an excellent overview on molecular electronics, see: Molecular Electronics: Science and Technology, Vol. 852 (Eds.: A. Aviram, M. Ratner), The New York Academy of Sciences, New York, 1998, and references therein.
38. R. E. Martin, F. Diederich, Angew. Chem. 1999, 111, 1440-1469; Angew. Chem. Int. Ed. 1999, 38, 1350-1377.
39. R. E. Martin, F. Diederich, Angew. Chem. 1999, 111, 1440-1469; Angew. Chem. Int. Ed. 1999, 38, 1350-1377.
40. K. Müllen, Pure Appl. Chem. 1993, 65, 89-96.
41. U. Scherf, K. Müllen, Synthesis 1992, 23-38.
42. R. E. Martin, U Gubler, C. Boudon, V. Gramlich, C. Bosshard, J.-P. Gisselbrecht, P. Günter, M. Gross, F. Diederich, Chem. Eur. J. 1997, 3, 1505-1512.
43. H. Meier, U. Stalmach, H. Kolshorn, Acta Polymer. 1997, 48, 379-384.
44. a) G. Zerbi, E. Galbiati, M. C. Gallazi, C. Castiglioni, M. Del Zoppo, R. Schenk, K. Müllen, J. Chem. Phys. 1996, 105, 2509-2516;
45. b) J. Grimme, M. Kreyenschmidt, F. Uckert, K. Müllen, U. Scherf, Adv. Mater. 1995, 7, 292-295;
46. c) J. Guay, P. Kasai, A. Diaz, R. Wu, J. M. Tour, L. H. Dao, Chem. Mater. 1992, 4, 1097-1105;
47. d) S. A. Jenekhe, Macromolecules 1990, 23, 2848-2854;
48. e) J. L. Brédas, R. Silbey, D. S. Boudreaux, R. R. Chance, J. Am. Chem. Soc. 1983, 105, 6555-6559.
49. a) G. Klaerner, R. D. Miller, Macromolecules 1998, 31, 2007-2009;
50. b) W. Li, T. Maddux, L. Yu, Macromolecules 1996, 29, 7329-7334.
51. D. L. Pearson, J. M. Tour, J. Org. Chem. 1997, 62, 1376-1387.
52. D. L. Pearson, J. S. Schumm, J. M. Tour, Macromolecules 1994, 27, 2348-2350.
53. T. Kauffmann, H. Lexy, Chem. Ber. 1981, 114, 3674-3683.
54. H.-P. Weitzel, A. Bohnen, K. Müllen, Makromol. Chem. 1990, 191, 2815-2835.
55. R. E. Martin, T. Mäder, F. Diederich, Angew. Chem. 1999, 111, 834-838; Angew. Chem. Int. Ed. 1999, 38, 817-821.
56. R. E. Martin, T. Mäder, F. Diederich, Angew. Chem. 1999, 111, 834-838; Angew. Chem. Int. Ed. 1999, 38, 817-821.
57. For a 12.8 nm long hexadecamer with a poly(p-phenylene ethynylene) backbone, see: J. S. Schumm, D. L. Pearson, J. M. Tour, Angew. Chem. 1994, 106, 1445-1448; Angew. Chem. Int. Ed. Engl. 1994, 33, 1360-1363.
58. For a 12.8 nm long hexadecamer with a poly(p-phenylene ethynylene) backbone, see: J. S. Schumm, D. L. Pearson, J. M. Tour, Angew. Chem. 1994, 106, 1445-1448; Angew. Chem. Int. Ed. Engl. 1994, 33, 1360-1363.
59. M. Schreiber, J. Anthony, F. Diederich, M. E. Spahr, R. Nesper, M. Hubrich, F. Bommeli, L. Degiorgi, P. Wachter, P. Kaatz, C. Bosshard, P. Günter, M. Colussi, U. W. Suter, C. Boudon, J.-P. Gisselbrecht, M. Gross, Adv. Mater. 1994, 6, 786-790.
60. J. Anthony, Ph. D. Thesis, University of California, Los Angeles, 1993.
61. R. E. Martin, J. Bartek, V. Gramlich, F. Diederich, R. R. Tykwinski, E. C. Meister, A. Hilger, H. P. Lüthi, J. Chem. Soc. Perkin Trans. 2 1998, 233-241.
62. a) A. M. Boldi, J. Anthony, C. B. Knobler, F. Diederich, Angew. Chem. 1992, 104, 1270-1273; Angew. Chem. Int. Ed. Engl. 1992, 31, 1240-1242;
63. a) A. M. Boldi, J. Anthony, C. B. Knobler, F. Diederich, Angew. Chem. 1992, 104, 1270-1273; Angew. Chem. Int. Ed. Engl. 1992, 31, 1240-1242;
64. b) J. Anthony, C. Boudon, F. Diederich, J.-P. Gisselbrecht, V. Gramlich, M. Gross, M. Hobi, P. Seiler, Angew. Chem. 1994, 106, 794-798; Angew. Chem. Int. Ed. Engl. 1994, 33, 763-766;
65. b) J. Anthony, C. Boudon, F. Diederich, J.-P. Gisselbrecht, V. Gramlich, M. Gross, M. Hobi, P. Seiler, Angew. Chem. 1994, 106, 794-798; Angew. Chem. Int. Ed. Engl. 1994, 33, 763-766;
66. c) A. M. Boldi, J. Anthony, V. Gramlich, C. B. Knobler, C. Boudon, J.-P. Gisselbrecht, M. Gross, F. Diederich, Helv. Chim. Acta 1995, 78, 779-796.
67. J. L. Brédas, J. Cornil, A. J. Heeger, Adv. Mater. 1996, 8, 447-452.
68. P. Bäuerle, Adv. Mater. 1992, 4, 102-107.
69. E. H. Elandaloussi, P. Frére, P. Richomme, J. Orduna, J. Garin, J. Roncali, J. Am. Chem. Soc. 1997, 119, 10774-10784.
70. R. Schenk, H. Gregorius, K. Meerholz, J. Heinze, K. Müllen, J. Am. Chem. Soc. 1991, 113, 2634-2647.
71. U. Stalmach, H. Kolshorn, I. Brehm, H. Meier, Liebigs Ann. 1996, 1449-1456.
72. D.-H. Hwang, B. S. Chuah, X.-C. Li, S. T. Kim, S. C. Moratti, A. B. Holmes, Macromol. Symp. 1997, 125, 111-120.
73. D. D. C. Bradley, Chem. Brit. 1991, 719-723.
74. R. E. Martin, J. A. Wytko, F. Diederich, C. Boudon, J.-P. Gisselbrecht, M. Gross, Helv. Chim. Acta 1999, 82, 1470-1485.
75. J. Cornil, D. Beljonne, J. L. Brédas in Electronic Materials: The Oligomer Approach (Eds.: K. Müllen, G. Wegner), WILEY-VCH, Weinheim, 1997, pp. 432-447.
76. D. Beljonne, J. Cornil, R. H. Friend, R. A. J. Janssen, J. L. Brédas, J. Am. Chem. Soc. 1996, 118, 6453-6461.
77. Z. Shuai, J. L. Brédas, S. K. Pati, S. Ramasesha, Proc. SPIE - Int. Soc. Opt. Eng. 1997, 3145, 293-302.
78. R. E. Martin, Dissertation, ETH Zürich, No. 12821, 1998.
79. The Chemistry of Organic Silicon Compounds (Eds.: S. Patai, Z. Rappoport), Wiley, Chichester, 1989.
80. J. M. Tour, R. Wu, Macromolecules 1992, 25, 1901-1907.
81. U. Gubler, C. Bosshard, P. Günter, M. Y. Balakina, J. Cornil, J. L. Brédas, R. E. Martin, F. Diederich, Opt. Lett. 1999, 24, 1599-1601.
82. J. L. Brédas, M. Dory, J. M. André, J. Chem. Phys. 1985, 83, 5242-5249.
83. U. Dinur, M. Karplus, Chem. Phys. Lett. 1982, 88, 171-176.
84. P. F. Coheur, J. Cornil, D. A. dos Santos, P. R. Birkett, J. Liévin, J. L. Brédas, D. R. M. Walton, R. Taylor, H. W. Kroto, R. Colin, unpublished results.
85. In terms of conformational and environmental effects that can promote shifts in the absorption maxima larger than the calculated energy differences, see for instance: D. Comoretto, I. Moggio, C. Cuniberti, G. Dellepiane, M. E. Giardini, A. Borghesi, Phys. Rev. B 1997, 56, 10264-10270.
86. J. L. Brédas, J. Cornil, D. Beljonne, D. A. dos Santos, Z. Shuai, Acc. Chem. Res. 1999, 32, 267-276.
87. a) F. Meyers, S. R. Marder, B. M. Pierce, J. L. Brédas, J. Am. Chem. Soc. 1994, 116, 10703-10714;
88. b) S. R. Marder, C. B. Gorman, F. Meyers, J. W. Perry, G. Bourhill, J.-L. Brédas, B. M. Pierce, Science 1994, 265, 632-635.
89. F. Kajzar, J. Messier, Phys. Rev. A 1985, 32, 2352-2363.
90. C. Bosshard in Nonlinear Optical Effects and Materials (Springer Series in Optical Sciences) (Ed.: P. Günter), Springer Verlag, Berlin, 1999.
91. M. Sheik-Bahae, A.A. Said, T.-H. Wei, D. J. Hagan, E. W. Van Stryland, IEEE J. Quantum Electron. 1990, 26, 760-769.
92. M. J. S. Dewar, E. G. Zoebisch, E. F. Healy, J. J. P. Stewart, J. Am. Chem. Soc. 1985, 107, 3902-3909.
93. J. Ridley, M. Zerner, Theor. Chim. Acta 1973, 32, 111-134.
94. J. L. Brédas, R. R. Chance, R. Silbey, G. Nicolas, P. Durand, J. Chem. Phys. 1981, 75, 255-267.
95. B. J. Orr, J. F. Ward, Mol. Phys. 1971, 20, 513-526.
96. Z. Shuai, J. L. Brédas, Phys. Rev. B 1991, 44, 5962-5965.