On the origin of optical activity in polythiophenes

Journal of Molecular Structure

Volumn 521, Issue 1-3, 2000, Pages 285-301

  Langeveld Voss, B M W ^a   Janssen, R A J ^a   Meijer, E W ^a  

^a EINDHOVEN UNIVERSITY OF TECHNOLOGY   (Netherlands)

Author keywords

Chirality; Circular dichroism; Conjugated polymers; Polythiophenes

Indexed keywords

POLYMER; THIOPHENE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHIRALITY; CIRCULAR DICHROISM; LIGHT ABSORPTION; OPTICAL ROTATION; POLARIZATION; REACTION ANALYSIS; STRUCTURE ANALYSIS;

EID: 0034724350     PISSN: 00222860     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0022-2860(99)00444-5     Document Type: Article

References (95)

1. For example, see Proceedings of the International Conference on Science and Technology of Synthetic Metals: (a) Synth. Met. 69-71 (1995).
2. (b) Synth. Met. 84-86 (1997).
3. Jehneke S.A., Osaheni J.A. Science. 265:1994;765.
4. Rumbles G., Samuel I.D.W., Magnani L., Murray K.A., DeMello A.J., Crystall B., Moratti S.C., Stone B.M., Holmes A.B., Friend R.H. Synth. Met. 76:1996;47.
5. Yassar A., Horowitz G., Valat P., Wintgens V., Hmyene M., Deloffre F., Srivastava P., Lang P., Garnier F. J. Phys. Chem. 99:1995;9155.
6. Samuel I.D.W., Rumbles G., Collison C. J. Phys. Rev. B. 52:1995;R11573.
7. Lemmer U., Heun S., Mahrt R.F., Scherf U., Hopmeier M., Siegner U., Göbel E.O., Müllen K., Bässler H. Chem. Phys. Lett. 240:1995;373.
8. Son S., Dodabalapur A., Lovinger A.J., Galvin M.E. Science. 261:1995;376.
9. Zerbi G., Castiglioni C., Delzoppo M. Müllen K., Wegner G. Electronic Materials: The Oligomer Approach. 1998;345 Wiley, Weinheim.
10. Pu L. Acta Polym. 48:1997;116.
11. Lemaire M., Delabouglise D., Garreau R., Roncali J. Torii S. Recent Advances in Electroorganic Synthesis. 1987;385 Elsevier, Amsterdam.
12. Lemaire M., Delabouglise D., Garreau R., Guy A., Roncali J. J. Chem. Soc., Chem. Commun. 1988;658.
13. Kotkar D., Joshi V., Ghosh P.K. J. Chem. Soc., Chem. Commun. 1988;917.
14. Roncali J., Garreau R., Delabouglise D., Garnier F., Lemaire M. Makromol. Chem. Makromol. Symp. 20/21:1998;601.
15. Roncali J., Garreau R., Delabouglise D., Garnier F., Lemaire M. Synth. Met. 28:1989;C341.
16. Andersson M., Ekeblad P.O., Hjertberg T., Wennerström O., Inganäs O. Polym. Commun. 30:1991;546.
17. Ochiai K., Tabuchi Y., Rikukawa M., Sanui K., Ogata N. Thin Solid Films. 329:1998;454.
18. Ochiai K., Rikukawa M., Sanui K., Ogata N., Ueno Y., Ema K. Synth. Met. 101:1998;84.
19. See for example, ICSM Book of Abstracts, July 12-18, 1998; Montpellier, France.
20. H. Guo, C.M. Knobler, R.B. Kaner, ICSM Book of Abstracts, July 12-18, 1998; Montpellier, France, p. 176.
21. W.E. Price, C.O. Too, G.G. Wallace, D. Zhou, ICSM Book of Abstracts, July 12-18, 1998; Montpellier, France, p. 228.
22. Sélégny E. Optically Active Polymers. 1979;D. Reidel, Dordrecht.
23. Wulff G. Angew. Chem., Int. Ed. Engl. 28:1989;21.
24. Okamoto Y., Nakano T. Chem. Rev. 94:1994;349.
25. Bouman M.M., Havinga E.E., Janssen R.A.J., Meijer E.W. Mol. Cryst. Liq. Cryst. 256:1994;439.
26. Bouman M.M., Meijer E.W. Adv. Mater. 7:1995;385.
27. Bidan G., Guillerez S., Sorokin V. Adv. Mater. 8:1996;157.
28. Andreani F., Angiolini L., Caretta D., Salatelli E. J. Mater. Chem. 8:1998;1109.
29. Ciardelli F., Lanzillo S., Pieroni O. Macromolecules. 7:1974;174.
30. Elsenbaumer R.L., Eckhardt H., Iqbal Z., Toth J., Baughman R.H. Mol. Cryst. Liq. Cryst. 118:1985;111.
31. Salmón M., Bidan G. J. Electrochem. Soc. 132:1985;1897.
32. Salmón M., Saloma M., Bidan G., Genies E.M. Electrochim. Acta. 34:1989;117.
33. Drake A.F., Udvarhelyi P., Ando D.J., Bloor D., Obhi J.S., Mann S. Polymer. 30:1989;1063.
34. Moore J.S., Gorman C.B., Grubbs R.H. J. Am. Chem. Soc. 113:1991;1704.
35. Yamaguchi M., Omata K., Hirama M. Chem. Lett. 1992;2261.
36. Moutett J.C., Saint-Aman E., Tran-Van F., Augibeaud P., Utille J.-P. Adv. Mater. 4:1992;511.
37. Aoki T., Kokai M., Shinohara K., Oikawa E. Chem. Lett. 1993;2009.
38. Harlev E., Wudl F. Salaneck W.R., Lundström I., Rånby B. Conjugated Polymers and Related Materials. The Interconnection between Chemical and Electronic Structure. Proc. Eighty-First Nobel Symposium. vol. 139:1993;Oxford University Press, Oxford.
39. Havinga E.E., Bouman M.M., Meijer E.W., Pomp A., Simenon M.M.J. Synth. Met. 66:1994;93.
40. Fiesel R., Huber J., Scherf U. Makromol. Rapid Commun. 15:1994;897.
41. Fiesel R., Huber J., Scherf U. Angew. Chem., Int. Ed. Engl. 35:1996;2111.
42. Peeters E., Delmotte A., Janssen R.A.J., Meijer E.W. Adv. Mater. 9:1997;493.
43. Fiesel R., Huber J., Apel U., Enkelmann V., Hentschke R., Scherf U. Macromol. Chem. Phys. 198:1997;2623.
44. Peeters E., Christiaans M.P.T., Janssen R.A.J., Schoo H.F.M., Dekkers H.P.J.M., Meijer E.W. J. Am. Chem. Soc. 119:1997;9909.
45. Pleus S., Schwiter M. Synt. Commun. 27:1997;2917.
46. Fiesel R., Scherf U. Macromol. Rapid Commun. 19:1998;427.
47. Andreani F., Angiolini L., Caretta D., Salatelli E. J. Mater. Chem. 8:1998;1109.
48. Fiesel R., Scherf U. Acta Polym. 49:1998;445.
49. Cornelissen J.J.L.M., Peeters E., Janssen R.A.J., Meijer E.W. Acta Polym. 49:1998;471.
50. Bloor D. Chem. Phys. Lett. 295:1998;63.
51. Langeveld-Voss B.M.W., Janssen R.A.J., Christiaans M.P.T., Meskers S.C.J., Dekkers H.P.J.M., Meijer E.W. J. Am. Chem. Soc. 118:1996;4908.
52. Langeveld-Voss B.M.W., Bouman M.M., Christiaans M.P.T., Janssen R.A.J., Meijer E.W. Polym. Prepr. 37:1996;499.
53. Langeveld-Voss B.M.W., Peeters E., Janssen R.A.J., Meijer E.W. Synth. Met. 84:1997;611.
54. Ramos Lermo M.E., Langeveld-Voss B.M.W., Meijer E.W. Polym. Prepr. 39:1998;1087.
55. Langeveld-Voss B.M.W., Christiaans M.P.T., Janssen R.A.J., Meijer E.W. Macromolecules. 31:1998;6702.
56. Goldoni F., Langeveld-Voss B.M.W., Meijer E.W. Synth. Commun. 28:1998;2237.
57. Langeveld-Voss B.M.W., Waterval R.J.M., Janssen R.A.J., Meijer E.W. Macromolecules. 32:1999;227.
58. Green M.M., Peterson N.C., Sato T., Teramoto A., Cook R., Lifson S. Science. 268:1995;1860. (and references therein).
59. Charney E. The Molecular Basis of Optical Activity: Optical Rotatory Dispersion and Circular Dichroism. 1979;Wiley, Chichester.
60. Dekkers H.P.J.M. Nakanishi K., Berova N., Woody R.W. Circular Dichroism: Principles and Applications. 1994;121 VCH, New York.
61. Riehl J.P., Richardson F.S. Chem. Rev. 86:1986;1.
62. Cui C.X., Kertesz M. Phys. Rev. B. 40:1989;9661.
63. Garnier F., Tourillon G., Barraud J.Y., Dexpert H. J. Mater. Sci. 20:1985;2687.
64. Lacaze E., Urdal K., Bodö P., Garbarz J., Salaneck W.R., Schott M. J. Polym. Sci., Polym. Phys. Ed. 31:1993;11.
65. Bäuerle P., Fischer T., Bidlingmeier B., Stabel A., Rabe J.P. Angew. Chem., Int. Ed. Engl. 34:1995;303.
66. Bäuerle P. Müllen K., Wegner G. Electronic Materials: The Oligomer Approach. 1998;105 VCH, Weinheim. chap. 2.
67. Gronowitz S., Moses P., Håkansson R. Arkiv Kemi. 16:1960;267.
68. Lawesson S. Acta Chem. Scand. 10:1956;1020.
69. Analogous to S. Gronowitz, Arkiv Kemi 12 (1958) 239.
70. A.G. Hoechst, German Patent DE 3804522 A1, 1989.
71. Goldoni F., Langeveld-Voss B.M.W., Meijer E.W. Synth. Commun. 28:1998;2237.
72. Sugimoto R.-I., Takeda S., Gu H.B., Yoshino K. Chem. Express. 1:1986;635.
73. + in our experiment (+0.47 V vs SCE) and the value reported by Dietrich et al. (+0.35 V vs Ag/AgCl)).
74. J.D. Moulton, Structure/property relationships of poly(3-alkylthiophene)s and their blends with ultra-high molecular weight polyethylene; Thesis, University of California, Santa Barbara, 1991.
75. Green B.S., Arad-Yellin R., Cohen M.D. Eliel E.L., Wilen S.H., Allinger N.L. Topics in Stereochemistry. vol. 16:1986;146 Wiley, New York.
76. Addadi L., Ariel S., Lahav M., Leiserowitz L., Popovich-Biro R., Tang C.P. Roberts M.W., Thomas J.M. Chemical Physics of Solids and Their Surfaces. vol. 8:1981;202-245 Chemical Society, London.
77. Benedith E., Pedone C., Sirigu A. Acta Cryst. 29B:1973;730.
78. Pelletier M., Brisse F. Acta Cryst. C. 50:1994;1942.
79. Paulus E.F., Dammel R., Kämpf G., Wegener P., Siam K., Wolinski K., Schäfer L. Acta Cryst. B. 44:1988;509.
80. Paulus E.F., Siam K., Wolinski K., Schäfer L. J. Molec. Struct. 196:1989;171.
81. Meille S.V., Farina A., Bezziccheri F., Galazzi M.C. Adv. Mater. 6:1994;848.
82. Pelletier M., Brisse F., Cloutier R., Leclerc M. Acta Cryst. C. 51:1995;1394.
83. Samuelsen E.J., Mårdalen J. Nalwa H.S. Handbook of Organic Conductive Molecules and Polymers. vol. 3:1997;87 Wiley, Chichester. chap. 2.
84. Prosa T.J., Winokur M.J., McCullough R.D. Macromolecules. 29:1996;3654.
85. Rughooputh S.D.D.V., Hotta S., Heeger A.J., Wudl F. J. Polym. Sci. Polym. Phys. Ed. 25:1987;1071.
86. Hagler T.W., Pakbaz K., Voss K.F., Heeger A.J. Phys. Rev. B. 44:1991;8652.
87. Salaneck W.R., Inganäs O., Thémans B., Nilsson J.O., Sjorgren B., Österholm J.-E., Brédas J.-L., Svensson S. J. Chem. Phys. 89:1988;4613.
88. Roux C., Bergeron J.-Y., Leclerc M. Makromol. Chem. 194:1993;869.
89. Daoust G., Leclerc M. Macromolecules. 24:1991;455.
90. Yue S., Berry G.C., McCullough R.D. Macromolecules. 29:1996;933.
91. Halliday D.A., Burn P.L., Bradley D.D.C., Friend R.H., Gelsen O.M., Holmes A.B., Kraft A., Martens J.H.F., Pichler K. Adv. Mater. 5:1993;40.
92. Langeveld-Voss B.M.W., Beljonne D., Shuai Z., Janssen R.A.J., Meskers S.C.J., Meijer E.W., Brédas J.L. Adv. Mater. 10:1998;1343.
93. Ikemoto H., Estevez I., Nakanishi K., Berova N. Heterocycles. 46:1997;489.
94. Harada N., Nakanishi K. Circular Dichroic Spectroscopy. Exciton Coupling in Organic Stereochemistry. 1983;Oxford University Press, Oxford.
95. Bongiovanni G., Botta C., Brédas J.L., Cornil J., Ferro D.R., Mura A., Piaggi A., Tubino R. Chem. Phys. Lett. 278:1997;146.