Abstract
Radical ions generated by electron transfer reactions are known as important intermediates in organic chemistry. On the other hand, their formation, recombination and transport in organic materials is responsible for a series of attractive physical properties. Radical ion formation is often accompanied by structural changes being well understood in small organic molecules, which also constitute repeating units of intensively studied macromolecules. Therefore, an approach is described herein to compare and combine the structural and energetic description of monomeric and oligomeric radical ions with that of partially oxidized or reduced polymeric materials.
Many optical and electrical properties of high-molecular-weight conjugated polymers closely correspond to those of oligomers containing only a few repeating units. These oligomers can be synthesized as monodisperse species, facilitating the spectroscopic description and enabling systematic studies of physical properties as a function of chain length (Sect. 2).
The mode of charge and spin distribution on conjugated chains is a central question for conducting polymers which are electrical insulators and semiconductors in the neutral, pristine state (Sect. 3). Both, intra- and interchain charge transport have to be considered in describing the overall conductivity. Electroactive polymers are applied as change storage materials, e.g. in rechargeable batteries, where the detailed charging mechanisms and minimization of Coulomic repulsion in highly charged states are crucial (Sect. 4). Electron transfer can also induce chemical reactions under formation or cleavage of σ-bonds (Sect. 5). While this is an unwanted side effect in the doping of conjugated polymers electrooxidation of suitable π-systems is a common method of producing electroactive and conducting polymers. Conductivity does not necessarily require polymeric materials, but is also obtained in radical ion salts and charge transfer complexes which are crystalline one dimensional conductors (Sect. 6). Their electrical conductivity can adequately be described as an electron hopping process between neighboring molecular layers. While the mobility of charge is important in processes like electrical conductivity or photo- and electroluminescence, localized radical states with as many unpaired electrons as possible are needed in magnetic materials (Sect. 7). Finally, the control of electron transfer processes in radical ion states can be used in molecular electronics (Sect. 8).
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10 References
Skotheim TA (ed) (1986) Handbook of conducting polymers. Marcel Dekker, New York
Brédas JL, Silbey R (eds) (1991) Conjugated polymers. Kluwer, Dordrecht
Naarmann H (1990) In: Brédas JL, Chance RR (eds) Conjugated polymeric materials: Opportunities in electronics, optoelectronics, and molecular electronics. Kluwer, Dordrecht, p 11
Law KY (1993) Chem Rev 93: 449
Bohnen A, Räder HJ, Müllen K (1992) Synth Met 47: 37
Colaneri NF, Bradley DDC, Friend RH, Burn PL, Holmes AB, Spangler CW (1990) Phys Rev B42: 11670
Burroughes JH, Bradley DDC, Brown AR, Marks N, Mackay K, Friend RH, Burn PL, Holmes AB (1990) Nature 347: 539
Müllen K (1984) Chem Rev 84: 603
Müllen K (1987) Angew Chem 99: 192; Int Ed Engl 26: 204
Roth HD (1992) Topics Curr Chem 163: 131
Boche G (1988) Topics Curr Chem 146: 1
Fox MA, Cannon M (eds) (1988) Photoinduced electron transfer. Elsevier, Amsterdam
Metzger RM, Panetta CA (1989) J Mol Electronics 5: 1
Heilbronner E, Bock H (1978) (eds) Das HMO Modell und seine Anwendungen. Verlag Chemie Weinheim
Heinze J (1984) Angew Chem 96: 823, Int Ed Eng 23: 831
Gerson F (1967) Hochauflösende ESR Spektroskopie. Verlag-Chemie Weinheim
Kurreck H, Kirste B, Lubitz W (1988) ENDOR spectroscopy of radicals in solution. In: Marchand AP (ed) Methods in stereochemical analysis, vol 15. VCH, Weinheim
Enkelmann V, Göckelmann K, Wieners G, Monkenbusch M (1985) Mol Cryst Liq Cryst 120: 195
Kröhnke C, Enkelmann V, Wegner G (1980) Angew Chem 92: 941 Int Ed Engl 19: 912
Huber W, May A, Müllen K (1981) Chem Ber 114: 1318
Huber W, Müllen K (1986) Acc Chem Res 19: 300
Gorman CB, Grubbs RH (1991) In: Brédas JL, Silbey R (eds) Conjugated polymers. Kluwer Dordrecht, p 1
Hörhold HH (1972) Z Chem 12:41
Meyer H (1992) Angew Chem 104: 1425; Int Ed Engl
Mazzugato U, Momiccioli F (1991) Chem Rev 91: 1679
Orlandi G, Zerbetto F, Zgierski MZ (1991) Chem Rev 91: 867
Bock H, Ruppert K, Fenske D (1989) Angew Chem 102: 548 Int Ed Engl 29: 525
Baumgarten M, Weitzel HP, Schulz A, Garay R, Müllen K (to be published)
Schenk R, Huber W, Schade P, Müllen K (1988) Chem Ber 121: 2201
Müllen K, Heinz W, Klärner FG, Roth WR, Kindermann, Adamczak O, Wette M, Lex J (1990) Chem Ber 123: 2349
Anet AL, Bourn AJR, Lin YS (1964) J Am Chem Soc 86: 3576
Lhost O, Brèdas JL (1992) J Chem Phys 96: 5279
Zerbi G, Gussoni M, Castiglioni C (1991) In: Brédas JL, Silbey R (eds) Conjugated Polymers. Kluwer, p 435
Chien JCW (ed) (1984) Polyacetylene: Chemistry, Physics and Material Science. Academic, San Diego
Ito T, Shirakawa H, Ikeda S (1974) J Polym Sci Polym Chem Ed 12: 11
Gibson HW, Kaplan S, Mosher RA Prest WM, Weagley RJ (1986) J Am Chem Soc 108: 6843
Pekker S, Janossy A (1986) In: Skotheim TA (ed) Handbook of Conducting Polymers. Marcel Dekker, New York, p 45
Müllen K (1986) Pure & Appl Chem 58: 177
Glasbeck M, van Voorst JDW, Hoijtink GJ (1966) J Chem Phys 45: 1852
Krusic PJ, Wasserman E (1991) J Am Chem Soc 113: 2322
Staley SW, Henry TJ (1969) J Am Chem Soc 91: 1239
Schröder G (ed) (1965) Cyclooctatetraen. Verlag Chemie, Weinheim.
Katz TJ, Garratt PJ (1964) J Am Chem Soc 86: 5194
Müllen K (1974) Helv Chim Acta 57: 2399
Oth JFM (1971) Pure & Appl Chem 25: 573
Oth JFM, Anthoine G, Gilles JM (1968) Tetrahedron Lett 6265
Müllen K, Meul T, Vogel E, Kürschner U, Schmickler H, Wennerström O (1985) Tetrahedron Lett. 26: 3091
Gust D, Senkler GH, Mislow K (1972) J Chem Soc Chem Commun 1345
Huber W (1985) Tetrahedron Lett 181
Baumgarten M, Müller U, Bohnen A, Müllen K (1992) Angew Chem 104: 482, Int Ed Engl 31: 448
Baumgarten M, Müller U (1993) Synth Met 57: 4751
Rabinovitz M (1988) Top Curr Chem 146: 99
Minsky A, Meyer AY, Rabinovitz M (1983) Angew Chem Int Ed Engl 22: 45
Minsky A, Rabinovitz M (1984) J Am Chem Soc 106: 6755
Gregorius H, Baumgarten M, Reuter R Tyutyulkov N, Müllen K (1992) Angew Chem 104: 1621 Int Ed Engl 31: 1653
Brédas JL, Heeger AJ (1990) Macromolecules 23: 1150
Baumgarten M, Huber W, Müllen K (1993) Adv Phys Org Chem 28: 1
Heinze J (1990) Topics Curr Chem 152: 1
Diaz AF, Bargon J (1986) In: Skotheim TA (ed) Handbook of conducting polymers. Marcel Dekker, New York, p 81
Treloar LRG (1958) Physics and chemistry of rubbeer elasticity. Clarendon, Oxford
Ward IM (1983) Mechanical properties of polymers. Wiley, Chichester
Hörhold HH, Helbig M (1987) Makromol Chem Macromol Symp 12: 229
Koßmehl G (1986) In: Skotheim TA Handbook of conducting polymers. M. Dekker, NY, p 351
Heeger AJ, Smith P (1991) In: Brédas JL, Silbey R (eds) Conjugated polymers. Kluwer, Dordrecht, p 141
Müllen K (1993) Pure & Appl Chem 65: 89
Bohnen A, Heitz W, Mülleen K, Räder HJ, Schenk R (1991) Makromol Chem 192: 1679
Rehahn M, Schlüter AD, Wegner G (1990) Makromol Chem 191: 1991
Shi S, Wudl F (1990) Macromolecules 23: 2119
Wegner G (1986) Makromol Chem Makromol Symp 1: 151
Schäfer-Siebert D, Budrowski C, Kuzmany H, Roth S (1987) In: Kuzmany H, Mehring M, Roth S (eds) Electronic properties of conjugated polymers. Solid State Sciences 76: 38
Kürti J, Kuzmany H (1987) In: Kuzmany H, Mehring M, Roth S (eds) Electronic properties of conjugated polymers, Solid State Sciences 76: 43
Bradley DDC, Friend RH, Feast WJ (1987) Synth Met 17: 645
Ringsdorf H, Schlarb B, Venzmer J (1988) Angew Chem 100: 117, Int Ed Engl 27: 113
Ito T, Shirakawa H, Ikeda S (1974) J Polym Sci Polym Chem Ed 12: 11
Naarmann H, Theophilou N (1987) Synth Met 22: 1
Feast WJ (1986) In: Skotheim TA (ed) Handbook of conducting polymers. Marcel Dekker, New York, p 1
Edwards JH, Fest EJ (1980) Polym Comm 21: 595
Gagnon DR, Capistran JD, Korasz FE, Lenz RW (1984) Polym Bull 12: 93
Wessling RA, Zimmermann RG (1968) US Patent 3: 401, 152
Wessling RA (1986) J Polym Sci Polym Symp 72: 55
Fahnenstich U, Koch KH, Müllen K (1989) Makromol Chem 10: 563
Müller U, Baumgarten M, Müllen K (1994) submitted
Weitzel HP, Müllen K (1990) Makromol Chem 191: 2837
Garay R, Baier U, Bubeck C, Müllen K (1993) Adv Mat 5: 568
Deronzier A, Moutet JC (1989) Acc Chem Res 22: 249
Chiang CK, Park YW, Heeger AJ, Shirakawa H, Louis EJ, McDiarmid YW (1977) Phys Rev Lett 39: 1098
Park YW, Heeger AJ, Druy MA, McDiarmid YW (1980) J Chem Phys 73: 946
Maaxfield M, Mu SI, MacDiarmid AG (1985) J Electrochem Soc 132: 838
Bittihn R, Ely G, Woffler F, Münstedt H, Naarmann H, Naegele D (1987) Makromol Chem Macromol Symp 8: 51
Baughman RH (1991) Makromol Chem Macromol Symp 51: 193
Lee BI (1992) Polymer Engineering and Science 32: 36
Tyutyulkov N, Karabunarliev S, Müllen K, Baumgarten M (1993) Synth Met 53: 205
Tanaka K, Koike T, Ueda K, Ohzeki K, Yamabe T (1985) Synth Met 11: 61
Lee YS, Kertesz M, Elsenbaumer RL (1990) Chem Mater 2: 526
Baumgarten M, Karabunarliev S, Koch KH, Müllen K, Tyutyulkov N (1992) Synth Met 47: 21
Scherf U, Müllen K (1992) Synthesis 1/2: 23
Scherf U, Müllen K (1992) Polym Commun 33: 2443
Hong SY, Kertesz M, Lee YS, Kim OK (1992) Macromolecules 25: 5424
Rughooputh SDDV, Hotta S, Heeger AJ, Wudl F (1987) J Polym Sci Polym Phys 25: 1071
Schimmel T, Gläser S, Schwoerer M, Naarmann H (1991) In: Brédas JL, Silbey R (eds) Conjugated polymers. Kluwer Academic Publishers, Netherlands, p 49
Rost A (1978) “Messung dielektrischer Stoffeigenschaften”, Akademie-Verlag, Berlin
Montgomery HC (1971) J Appl Phys 42: 2971
Wegner G (1981) Angew Chem 93: 352 Int Ed Engl 20:361
Alcazar L (1980) “The physics and chemistry of low dimensional solids”, Reidel, Dordrecht
Menke K, Roth S (1986) ChIUZ 20: 1, 33
Chance RR, Boudreaux DS, Brédas JL, Silbey R (1986) In: Skotheim TA (ed) Handbook of conducting polymers. Marcel Dekker, New York, p 825
Heeger AJ, Kivelson S, Schrieffer JR, Su WP (1988) Rev Mod Phys 60: 781
Bernier P (1986) In: Skotheim TA (ed) Handbook of conducting polymers. Marcel Dekker, New York, p 1099
Thomann H, Dalton LR (1986) Skotheim TA (ed) Handbook of conducting polymers, Marcel Dekker, New York, p 1157
Mehring M, Grupp A, Hofer P, Kass H (1989) Synth Met 28: D399
Nechtschein M, Devreux F, Genoud F, Gugliani M, Holcer K (1983) Phys Rev B 27: 61
Brédas JL, Street GB (1985) Acc Chem Res 18: 309
Brédas JL (1986) In: Skotheim TA (ed) Handbook of conducting polymers, Marcel Dekker, New York, p 859
Vogel P, Campbell DK (1990) Phys Rev B 41: 12797
Ofer D, Crooks RM, Wrighton MS (1990) J Am Chem Soc 112: 7869
Schenk R, Gregorius H, Meerholz K, Heinze J, Müllen K (1991) J Am Chem Soc 113: 2634
Schenk R, Ehrenfreund M, Huber W, Müllen K (1990) J Chem Soc Chem Commun 23: 1673
Schenk R, Gregorius H, Müllen K (1991) Adv Mat 3: 492
Heinze J, Mortensen J, Müllen K, Schenk R (1987) Chem Commun 701
Meerholz K, Schenk R, Müllen K, Heinze J (1994) to be published
Tian B, Zerbi G, Schenk R, Müllen K (1991) J Chem Phys 95: 3191
Tian B, Zerbi G, Müllen K (1991) J Chem Phys 95: 3198
Woo HS, Lhost O, Graham SC, Bradley DDC, Friend RH, Quattrocchi C, Brédas JL, Schenk R, Müllen K (1993) Synth Met 59: 13–28
Brendel P, Grupp A, Mehring M, Schenk R, Müllen K, Huber W (1991) Synth Met 45: 49
Plato M, Biehl R, Möbius K, Dinse KP (1976) Z Naturforsch A 31: 169
Huber W, May A, Müllen K (1981) Chem Ber 114: 1318
Rabinovitz M, Willner L, Minsky A (1983) Acc Chem Res 16: 298
Chang R, Markgraf JH (1972) Chem Phys Lett 13: 575
Schenk R, Hucker J, Hopf H, Räder HJ, Müllen K (1989) Angew Chem 101: 942–944; Int Ed Engl 28: 904
Thulin B, Wennerström O (1976) Acta Scand B B30: 369
Huber W, Müllen K, Wennerström O (1980) Angew Chem 92: 636; Int Ed Engl 19: 624
Müllen K, Unterberg H, Huber W, Wennerström O, Norinder U, Tanner D (1984) J Am Chem Soc 106: 7514
Schenk R, Huber W, Schade P, Müllen K (1988) Chem Ber 121: 2201
Schenk (1991) PhD thesis Mainz
Spangler CW, Hall TJ, Sypochak LS, Liu PK (1989) Polymer 30: 1166
Hogen-Esch TE (1977) Adv Phys Org Chem 15:153
Koch KH, Fahnenstich U, Baumgarten M, Müllen K (1991) Synth Met 41: 1619
Koch KH, Müllen K (1992) Chem Ber 124: 2091
Baumagarten M, Anton U, Gherghel L, Müllen K (1993) Synth Met 57: 4801
Baumgarten M, Koch KH, Müllen K (1993) J Am Chem Soc (submitted)
Viruela-Martin R, Viruela-Martin PM, Orti E (1992) J Chem Phys 97: 8470
Bakhshi AK, Ladik J (1989) Synth Met 30: 115
Böhm A, Mauermann H, Gherghel L, Baumgarten M, Müllen K (1993) to be published
Böhm A, Adam M, Mauermann H, Stein S, Müllen K (1992) Tetrahedron Lett 33: 2795
Böhm A (1991) PhD thesis
Karabunarliev S, Baumgarten M, Gregorius H, Müllen K, Tyuytulkov N (1994) to be published
Heitz W, Ullrich R (1966) Makromol Chem 98: 29
Gregorius H, Heitz H, Müllen K (1993) Adv Mat 5: 279
Dawe EA, Land EJ (1975) J Chem Soc Faraday Trans I 72: 2162
Lafferty J, Roach A, Sinclair RS, Truscott TG, Land EJ (1977) J Chem Soc Faraday Trans I 73: 416
Knoll K, Schrock RR (1989) J Am Chem Soc 111: 7989
Bally T, Roth K, Tang W, Schrock RR, Knoll K, Park LY (1992) J Am Chem Soc 114: 2440
Kiehl A, Eberhard A, Adam M, Enkelmann V, Müllen K (1992) Angew Chem 104: 1623 Int Ed Engl
Kiehl A (1993) PhD thesis Mainz
Kiehl A, Eberhard A, Müllen K, Gherghel L, Baumgarten M (1993) (to be published)
Tolbert LM, Ogle ME (1990) J Am Chem Soc 112: 9512
Deussen M, Bässler H (1992) Chem Phys 164: 247
Bässler H, Deussen M, Heun S, Lemmer U, Mahrt RF (1993) Z Phys Chem N F (in press)
Kohler BE, Spangler CW, Westerrfield C (1988) J Chem Phys 89: 3422
Frank J, Grimme W, Lex J (1978) Angew Chem 90:1002; Int Ed Engl 17: 943
Huber W, Müllen K, Busch R, Grimme W, Heinze J (1982) Angew Chem 94: 294; Int Ed Engl 21: 301
Heinze J, Dietrich M, Hinkelmann K, Meerholz K, Rashwan (1989) Dechema Monogr 112: 61; Chem Abstr 110: 221 359r
Heinz W, Langensee P, Müllen K (1986) J Chem Soc Chem Commun 947
Heinze J (private communication)
Huber W (1985) Tetrahedron Lett 181
It should be noted in the characterization of radical anions by absorption spectroscopy that even traces of water give rise to rapid protonations of the charged species originally obtained. This quenching process is particularly critical for the sparingly soluble higher oligomers. The dihydro products thus formed still possess shorter phenylenevinylene electrophores, which undergo further reduction and thus give rise to false signal assignment.
Fichou D, Xu B, Horrowitz G, Garnier F (1991) Synth Met 41: 463
Horrowitz G, Peng X-Z, Fichou D, Garnier F (1991) J Molec Electr 7: 85
Havinga EE, Rotte I, Meijer EW, Hoeve WT, Wynberg H (1991) Synth Met 41: 473
Yassar A, Delabouglise D, Hmyene M, Nessak B, Horrowitz G, Garnier F (1992) Adv Mater 4: 490
Bäuerle P, Adv Mater (1992), 4, 102
Bäuerle P, Segelbacher U, Gaudl GU, Huttenlocher D, Mehring M (1993) Angew Chem, 105: 125.
Segelbacher U, Sariftci NS, Grupp A, Bäuerle P, Mehring M (1993) Synth Met 55–57: 4728
Ehrendorfer C, Neugebauer H, Neckel A, Bäuerle P (1993) Synth Met 55–57: 493
Bäuerle P, Götz G, Segelbacher U, Huttenlocher D, Mehring M (1993) Synth Met 55–57: 4768
Bäuerle P, Gaudl KU (1991) Synth Met 43: 3037
Martina A, Enkelmann V, Schlüter AD, Wegner G (1992) Synth Met 51: 299
Zotti G, Martina S, Wegner G, Schlüter AD (1992) Adv Mater 4: 798
Martina S, Enkelmann V, Wegner G, Schlüter AD, Zotti G, Zerbi G (1993) Synth Met (in press)
Wegner G (1984) In: Van der berg EJ (ed) Contemporary topics in polymer science. Plenum, New York p 281
Soos ZG, Hayden GW (1991) In: Skotheim TA (ed) Electroresponsive molecular and polymeric systems. Marcel Dekker, New York, p 197
Roth S (1986) In: Pollak M, Shklovskii BI (eds) Hopping transport in solids. Elsevier, Amsterdam p 378
Meerholz K, Heinze J (1993) Synth Met 55–57: 5040
Kuzmany H, Mehring M, Roth S (eds) (1989) Electronic properties of conjugated polymers III, part 1. Springer, Berlin Heidelberg New York
Sheng P (1980) Phys Rev Lett 45: 60
Karl N (1974) Adv Sol State Phys 14: 261
Garnier F (1993) Lecture hold at the Kern-Symposium, Mainz
Becker B, Bohnen A, Ehrenfreund M, Wohlfarth W, Sakata Y, Huber W, Müllen K (1991) J Am Chem Soc 113: 1121
Böttger H, Bryksin VV (1985) (eds) Hopping conduction in solids. VCH, Weinheim
Fritsche H, Pollak M (1990) (eds) Hopping and related phenomena. World Scientific Publishers, Singapore
Pollak M, Shklovskii BI (1991) (eds) Hopping transport in solids Elsevier. Amsterdam
Mott NF, Davis EA (eds) (1979) Electronic processes in non-crystalline materials. Clarendon, Oxford
Gorham-Bergeron E, Emin D (1977) Phys Rev B 15: 3667
Schimmel TH, Denninger G, Riess W, Voit J, Schwoerer M, Schoeppe W, Naarmann H (1989) Synth Met 28: D11
Halim J, Enkelmann V, Fischer H, Wegner G, Albouy PA (1991) Macromol Chem, Rap Commun 12: 301
Kaiser AB (1991) Synth Met 41: 183
Tritthart W, Leising G (1993) Synth Met 55–57: 4878
Enkelmann V, Halim J, Fischer H, Wegner G, Albouy PA (1992) Synth Met 51: 1
Baughman RH, Brédas JL, Chance RR, Elsenbaumer RL, Schacklette LW (1982) Chem Rev 82: 209.
Roth S, Menke K (1983) Kunststoffe 73: 520.
Nowak RJ, Schultz FA, Umana M, Lam R, Murray RW (1980) Anal Chem 52: 315.
Murray RW, Bard AJ (eds) (1984) Electroanalytical chemistry. Marcel Dekker, New York, 13: 191.
Shacklette LW, Chance RR, Ivory DM, Miller GG, Baughman RH (1979) Synth Met 1: 307.
Diaz AF, Kanazawa KK, Gardini GP (1979) J Chem Soc Commun 635.
Tourillon G, Garnier F (1982) J Electroanal Chem 135: 173
Diaz AF, Logan JA (1980) J Electroanal Chem 111: 111
Heinze J, Mortensen J, Störzbach (1987) In: Kuzmany H, Mehring M, Roth S (eds) Electronic properties of conjugated polymers. Springer, Berlin Heidelberg New York p 385
Bartz T, Klapper M, Müllen K, Schulz RC (1993) Polym Int 31: 153
Bender D, Przybylski M, Müllen K (1989) Makromol Chem 190: 2071
Smith TW, Kuder JE, Wychick (1976) J Polym Sci 14: 2433
Flanagan JB, Margel S, Bard AJ, Anson FC (1978) J Am Chem Soc 100: 4248
Saji T, Pasch NF, Webber SE, Bard AJ (1978) J Phys Chem 82: 1101
Hörhold HH, Opfermann J, Atrat P, Tauer KD, Drefahl G (1976) Polycondensation Processes. 5th Int Symp Polycondensation, Varna, Publication of the Bulgarian academy of Science, Bulgaria, Sofia p 171
Alexander J, Ehrenfreund M, Fiedler J, Huber W, Räder HJ, Müllen K (1989) Angew Chem 101: 1530; Int Ed Engl 28: 1531
Kovacic P, Kyriakis A (1963) J Am Chem Soc 85: 454
Ohlemacher A, Schenk R, Weitzel HP, Tyutyulkov N, Tasseva M, Müllen K (1992) Makromol 193: 81
Huber W, Irmen W, Lex J, Müllen K (1982) Tetrahedron Lett 23: 3889
Mortensen J, Heinze J, Herbst H, Müllen K (1992) J Electroanal Chem 324: 201
Hörhold HH, Helbig M, Raabe D, Opfermann J, Scherf U, Stockmann R, Weiß D (1987) Z Chem 27: 126
Genies EM, Pernaut JM (1985) J Electroanal Chem 191: 111
Meerholz K, Heinze J (1990) Angew Chem 102: 695 Int Ed Engl 29: 692
Genies EM, Pernault JM (1984) Synth Met 10: 117
Zhou QX, Kolaskie CJ, Miller LL (1987) J Electroanal Chem 223: 283
Daum P, Murray RW (1981) J Phys Chem 85: 389
Heinze J, Störzbach M, Mortensen J (1987) Ber Bunsenges Phys Chem 91: 960
Diaz AF, Crowley J, Bargon J, Gardini GP, Torrance JB (1981) J Electroanal Chem 121: 355
Nigrey PJ, MacDiarmid AG, Heeger AJ (1982) Mol Cryst Liq Cryst 83: 309
Tourillon G, Garnier F (1984) J Electroanal Chem 161: 55
Heinze J, Dietrich M, Mortensen J (1987) Makromol Chem Macromol Symp 8: 73
Feldberg SW (1984) J Am Chem Soc 106: 4671
Bohnen A, Koch KH, Lüttke W, Müllen K (1990) Angew Chem 102: 548; Int Ed Eng 29: 525
Bohnen A (1992) PhD thesis, Mainz, FRG
Schulz A, Koch KH, Müllen K, Heinze J (1994) to be published
Heinze J, Dietrich M (1989) Mater Sci For 42: 63
Heinze J, Bilger R, Meerholz K (1988) Ber Bunsenges Phys Chem 92: 1266
Hutton Rs, Kalaji M, Peter LM (1989) J Electroanal Chem 270: 429
Gamba A, Rusconi E, Simonetta (1970) Tetrahedron 26: 871
Wilson KE, Pincock PE (1977) Can J Chem 55: 889
Dietrich M, Heinze J (1990) J Am Chem Soc 112: 5142
Subaric-Leitis a, Monte C, Roggan A, Rettig W, Zimmermann P, Heinze J (1990) J Chem Phys 93: 4543
Mataga N, Yao H, Okada T, Rettig W (1989) J Phys Chem 93: 3383
Dietrich M, Mortensen J, Heinze J (1985) Angew Chem 97: 502 Int Ed Engl 24: 508
Müllen K, Baumgarten M, Karabunarliev S, Tyutyulkov N (1991) Synth Met 40: 127
Baumgarten M, Anton U, Gherghel L, Müllen K (1993) Synth Met 55–57: 4801
Weitzel HP, Bohnen A, Müllen K (1990) Makromol Chem 191: 2815
Heunt S, Mahrt RF, Greiner A, Lemmer U, Bässler H, Halliday DA, Bradley DDC, Burn PL, Holmes AB (1993) J Phys Condens Matter 5: 247
Anton U, Bohnen A, Koch KH, Naarmann H, Räder HJ, Müllen K (1992) Adv Mater 4: 91
Oth JFM, Gilles JM, Woo EP, Sondheimer F (1972) J Chem Soc Perkin II
Müllen K, Huber W, Nakagawa M, Iyoda M (1982) J Am Chem Soc 104: 5403
Becker BC, Huber W, Schnieders C, Müllen K (1983) Chem Ber 116: 1573
Müllen K, Huber W, Meul T, Nakagawa M, Iyoda M (1983) Tetrahedron 39: 1575
Becker BC, Huber W, Müllen K (1980) J Am Chem Soc 102: 7803
Müllen K, Oth JFM, Engels HW, Vogel E (1979) Angew Chem 91: 251; Int Ed Engl 18: 229
Auchter-Krummel P, Müllen K (1991) Angew Chem 103: 996, Int Ed Engl 30: 1003
Fry AJ, Hutchins CS (1975) J Am Chem Soc 97: 591
Allendoerfer RD, Rieger (1965) J Am Chem Soc 87: 2336
Staley SW, Dustman CK, Facchine KL, Linkowsky GE (1985) J Am Chem Soc 107: 4003
Tourillon G, Garnier F (1983) J Phys Chem 87: 2289
Salmon M, Diaz AF, Logan AJ, Krounbi M, Bargon J (1982) Mol Cryst Liq Cryst 83: 1297
Hotta S, Hosaka T, Shimotsuma W (1983) Synth Met 6: 69
Chung TC, Kaufman JH, Heeger AJ, Wudl F (1984) Phys Rev 30B: 702
Shaklette LW, Elsenbaumer RL, Baughman RH (1983) J Phys Coll 44C3: 559
Dietrich M, Mortensen J, Heinze J (1986) J Chem Soc Chem Commun: 1131
Bittihn R (1985) In: Kuzmany H, Mehring M, Roth S (eds) Electronic properties of conducting polymers I. Springer, Berlin Heidelberg New York, p 206
Shacklette LW, Maxfield M, Gould S, Wolf JF, Jow TR, Baughman RH (1987) Synth Met 18: 611
Anton U, Müllen K (1993) Makromol Chem 14, 223–229 (1993)
Beck F (1974) Elektroorganische Chemie. VCH Weinheim
Baizer MM, Lund H (1983) Organic electrochemistry. Marcel Dekker, New York.
Breitenbach M, Heckner KH (1973) J Electroanal Chem 43: 267.
Kobayashi T, Yaneyama H, Tamura H (1984) J Electroanal Chem 161: 419
Huang WS, Humphrey BD, MacDiarmid AG (1986) J Chem Soc Faraday Trans I, 82: 2385
Chiang JC, Mac Diarmid AG (1986) Synth Met 13: 193
Boudreaux DS, Chance RR, Wolf JF, Shacklette LW, Brédas JL, Thémans B, André JM, Silbey R (1986) J Chem Phys 85: 4584
Genies EM, Lapkowski M (1987) J Electroanal Chem 220: 67
Genies EM, Lapkowski M (1987) Synth Met 21: 117
Kovacic P, Koch FW (1965) J Org Chem 30: 3177
Kovacic P, (1981) J Polym Sci Polym Lett 19: 359
Heinze J (1981) Angew Chem 93: 183; Int Ed Engl 20: 202
Giese B (1985) Nachr Chem Tech Lab 33: 298
Giese B (1989) In: Regitz M, Giese B (eds) C-Radikale. Houben-Weyl Methoden der organischen Chemie Band E19a/Teil 1, p 1
Dodd JW (1971) J Chem Soc (B) Phys Org 2427
Kira A, Imamura M (1979) J Phys Chem 83: 2267
Huber W, Unterberg H, Müllen K (1983) Angew Chem 96: 800; Int Ed Engl 22: 242
Heinze J, Serafimov O, Zimmermann HW (1974) Ber Bunsenges 78: 652
Roth HD (1987) Acc Chem Res 20: 343
Parker VD (1983) Adv Phys Org Chem 19: 131
Torrance JB (1979) Acc Chem Res 12: 79
Freeman GR, Patai S, Zabicky J (1970) The Chemistry of Functional Groups: The chemistry of the carbonyl group, Wiley, London, vol 2, p 343
Metzger JO (1989) In: Regitz M, Giese B (eds) C-Radikale. Houben-Weyl Methoden der organischen chemie Band E19a/Teil 1, p 109 a 192
Oda M, to be published
Hirabayashi T, Naoi K, Osaka T (1987) J Electrochem Soc 134: 758
Edlund U, Eliasson B (1982) J Chem Soc Chem Commun 950
Baizer MM (1964) J Electrochem Soc 111: 215
Beck F (1965) Chem-Ing Techn 37: 607
Szwarc M (1956) Nature 178: 1168
Schäfer H (1970) Chem Ing Tech 42, 164
Ziegler K (1936) Angew Chem 49: 499
Morton M (1983) Anionic polymerization: principles and practice. Academic, New York, p 103
Morton M, Fetters LJ (1975) Rubber Chem Technol 48: 359
Uranek CA (1971) J Polym Sci Polym Chem Ed 9: 2273
Schue F, Worsfold DJ, Bywater S (1970) Macromolecules 3: 509
Vracken A, Smid J, Szwarc M (1962) J Chem Soc Farad Trans 55: 2036
McCormick HW (1957) Pol Sci 25: 488
Bargon J, Mohammed S, Waltmann RJ (1983) IBM J Res Develop 27: 330
Daub J (1987) Chimia 41: 52
Street GB (1986) In: Skotheim TA (ed) Handbook of conducting polymers. Marcel Dekker, New York, p 265
Genies EM, Bidan G, Diza AF (1983) J Electroanal Chem 149: 101
Inoue T, Yamase T (1983) Bull Chem Soc Jpn 56: 985
Kossmehl G, Chatzitheodorou G (1982) Makromol Chem Rapid Commun 2: 551
Diaz AF, Castillo JI, Logan JA, Lee WY (1982) J Electroanal Chem 129: 115
Waltman RJ, Diaz AF, Bargon J (1984) J Phys Chem 88: 4343
Waltman RJ, Bargon J (1984) Can J Chem 64: 76
Street GB, Lindsy SE, Nazzal AlWynne KJ (1985) Mol Cryst Liq Cryst 118: 137
Aalstad B, Ronlan A, Parker VD (1981) Acta Chem Scand B35: 649
Shirota Y, Noma N, Shimizu Y, Kanega H, Jeon IR, Nawa K, Kakuta T, Yasui H, Namba K (1991) Synth Met 41–43: 3031
Koch W, Heitz W (1983) Makromol Chem 184: 779
Bunnett JF (1978) Acc Chem Res 11, 413
Bellville DJ, Wirth DD, Bauld NL (1981) J Am Chem Soc 103: 718
Harirchian B, Bauld NL (1987) Tetrahedron Lett 927
Mlcoch J, Steckhahn E (1987) Tetrahedron Lett 1081
Müllen K, Huber W (1978) Helv Chim Achta 61: 1310
Böhm A, Müllen K (1992) Tetrahedron Lett 33: 611
Böhm A, Meerholz K, Heinze J, Müllen K (1992) J Am Chem Soc 114: 688
Laarhoven WH, Duppen THJHM (1972) J Chem Soc Perkin Trans 1: 2074
ophetVield PHG, Laarhoven WH (1977) J Chem Soc Perkin Trans 2: 268
Laarhoven WH, Cuppe TJHM, Niverd RJF (1970) Tetrahedron 26: 1069
Bartz T, Böhm A, Klapper M, Müllen K, Weitzel HP (1992) Makromol Chem 54–55: 495
Böhm A, Fiesser G, Mauermann H, Stein S, Müllen K (1994) in preparation
Schlüter AD (1991) Adv Mater 3: 282
Wegener S, Müllen K (1993) Macromolecules 26: 3037
Anton U, Müllen K (1993) Macromolecules 26: 1248
Hörhold HH (1993) Proc. Macromol. 70/71: “34th IUPAC Sympos on Macromolecules, 13–18th July 1992, Prague”
Enkelmann V (1988) In: Ebert B (ed) Polynuclear aromatic compounds. Chap 11, Adv Chem Ser 217: 177
Chiang TC, Reddoch AH, Williams J (1971) J Chem Phys 54: 2051
Jost W, Adam M, Enkelmann V, Müllen K (1992) Angew Chem 104: 883
Keller HJ, Nöthe D, Pritzkow H, Wehe D, Werner M, Koch P, Schweitzer D (1981) Mol Cryst Liq Cryst 62: 181
Endres H, Keller HJ, Müller B, Schweitzer D (1985) Acta Cryst C41: 607
Eichele H, Schwoerer M, Kröhnke C, Wegner G (1981) Chem Phys Lett 77: 311
Sigg J, Prisner T, Dinse KP, Brunner H, Schweitzer D, Hausser KH (1983) Phys Rev B 27: 5366
Denninger G, Stöcklein W, Dormann E, Schwoerer M (1984) Chem Phys Lett 107: 222
Maresch GG, Mehring M, vonSchütz JU, Werner HU, Gökelmann K, Enkelmann V, Müllen K, Klabunde KU (1989) J Chem Phys 91: 4543
Alexander J, Ehrenfreund M, Fiedler J, Huber W, Räder HJ, Müllen K (1989) Angew Chem 101: 1530; Int Ed Engl 28: 1531
Irmen W, Huber W, Lex J, Müllen K (1984) Angew Chem 96: 800; Int Ed Engl 23: 818
Bock H, Herrmann HF, Fenske D, Goesmann H (1988) Angew Chem 100: 1125; Int Ed Engl 27: 1067
Jost W, Adam M, Enkelmann V, Müllen K (1992) Angew Chem 104: 883
Zinke A, Linner F, Wolfbauer O (1925) Ber Dtsch Chem Ges 58: 323
Akamatu H, Inokuchi H, Matsunaga Y (1954) Nature 173: 168
Coffen DL, Garret PE (1969) Tetrahedron Lett 2043
Ferraris J, Cowan DO, Bloch AN (1974) J Chem Soc Chem Commun 937
Garito AF, Heeger AJ (1974) Acc Chem Res 7: 232
Almen G, Bauer T, Hünig S, Kupcik V, Langohr U, Metzenheim T, Meyer K, Rieder H, vonSchütz JU, Tillmanns E, Wolf HC (1991) Angew Chem 103: 608; Int Ed Engl 30: 561
Torrance JB, Tomkiewicz Y (1976) Bull Am Phys Soc 21: 313
Torrance JB, Silverman BD (1977) Phys Rev B 15: 788
Wudl F (1982) Pure & Appl Chem 54: 1051
Epstein AJ, Lipari NO, Sandman DJ, Nielson (1976) Phys Rev B 13: 1569
Hubbard J (1978) Phys Rev B 17: 494
Comés R (1977) In: Keller HJ (ed) Chemistry and physics of one dimensional metals. NATO Adv Study Institutes Series, B-Physics, Plenum, NY, 25: 315
Pauling L (1960) The nature of chemical bond. Ithaca, NY, p 511
Klots CE, Compton RN, Raaen VF (1974) J Chem Phys 60: 1177
Sandman DJ (1979) Mol Cryst Liq Cryst 50: 235
Metzger RM (1975) J Chem Phys 63: 5090
Kistenmacher TJ, Phillips TE, Cowan DO (1974) Acta Cryst B30: 763
Phillips TE, Kistenmacher TJ, Bloch AN, Ferraris JP, Cowan DO (1977) Acta cryst B33: 422
Aumüller A, Hünig S (1984) Angew chem 96:437; Int Ed Engl 23: 447
Hünig S, Aumüller A, Erk P, Meixner H, von Schütz JU, Gross HJ, Langohr U, Werner HP, Wolf HC, Burschka C, Klebe G, Peters K, von Schnering HG (1988) Synth Met 27: B181
Enkelmann V (1991) Angew Chem 103: 1142
Aumüller A, Erk P, Klebe G, Hünig S, vonSchütz JU, Werner HP (1986) Angew Chem 98: 759; Int Ed Engl 25: 740
Bechgaard K, Jakobsen CS, Mortensen K, Pederson MJ, Thorup N (1980) Solid State Commun 33: 1119
Bechgaard K, Carneiro K, Rasmussen FG, Olsen K, Rindorf G, Jakobsen CS, Pederson HJ, Scott JE (1981) J Am Chem Soc 103: 2440
Mizuno M, Garito AF, Cava MP (1978) J Chem Soc Chem Commun 18
Williams JM, Ferraro JR, Thorn RJ, Carlson KD, Geiser U, Wang HH, Kini AM, Whangbo MH (eds) Organic Superconductors, Synthesis, Structure, Properties, and Theory. Prentice Hall, Englewood Cliffs NJ
Urayama H, Yamochi H, Saito G, Nozawa K, Sugano T, Kinoshita M, Sato S, Oshima K, Kawamoto A, Tanaka J (1988) Chem Lett 55
Kini AM, Geiser U, Wang HH, Carlson KD, Williams JM, Kwok WK, Vandervoort KG, Thompson JE, Stupka DL, Jung D, Whangbo MH (1990) Inorg Chem 29: 2555
Pitman CU, Narita, Liang YF (1976) J Org Chem 41: 2855
Bryce MR, Moore AJ (1990) Pure & Appl Chem 62: 473
Sugimoto T, Awaji H, sugimoto I, Misaki Y, Kawase T, Yoneda S, Yoshida Z, Kobayashi T, Anzai H (1989) Chem Mater 1: 535
Sugiomoto T, Awaji H, Misaki Y, Yoshida Z, Kai Y, Nakagawa H, Kasai N (1985) J Am Chem Soc 107: 5792
Adam M, Wolf P, Räder HJ, Müllen K (1990) J Chem Soc Chem Commun 1624
Adam M, Müllen K (1993) Adv Mater submitted
Iwamura H (1990) Adv Pys Org. Chem 26: 179
Iwamura H, Miller JS (1993) Proceedings of the Symposium on the “CHEMISTRY AND PHYSICS OF MOLECULAR BASED MAGNETIC MATERIALS”. Mol Cryst Liqu Cryst 232/233: 1-360/1-366
Dougherty DA (1991) Acc Chem Res 24: 88
Miller JS, Epstein AJ, Reiff WM (1988) Acc Chem Res 21: 114
Miller JS, Dougherty DA (eds) (1989) Proceedings of the Symposium of Ferromagnetic and high spin molecular based materials. Mol Cryst Liq Cryst 176: 1
Heisenberg W (1928) Z Phys 49: 619
Bencini A, Gatteschi D (1990) EPR of exchange coupled system. Springer Verlag, Heidelberg.
Anderson PW (1963) In: Rado GT, Suhl H (eds) Magnetism. Academic, New York, vol 1 p 25
Hay PJ, Thibeault JC, Hoffmann RH (1975) J Am Chem Soc 97: 4884
Kramers HA (1934) Physica 1: 182
Anderson PW (1959) Phys Rev 115: 2
Tyutyulkov N, Karabunarliev S, Müllen K, Baumgarten M (1992) Synth Met 52: 71
Buchachenko A (1989) Mol Cryst Liq Cryst 176: 307
LePage TJ, Breslow R (1987) J Am Chem Soc 109: 6412
Miller JS, Epstein AS (1993) Angew Chem in press
McConnell HM (1963) J Chem Phys 1963 39, 1910
Mataga N, Theor Chim Acta 1968, 10, 372
Ovchinnikov AA (1978) Theor Chim Acta 47: 297
Aoki Y, Imamura A (1992) Theor Chim Acta 84: 155
McConnell (1967) Proc RA Welsh Found Conf Chem Res 11: 144
Breslow R, Juan B, Klutz RQ, Xia CZ (1982) Tetrahedron 38: 863
Miller JS, Epstein AJ (1989) Mol Cryst Liq Cryst 176: 347
Miller JS, Epstein AJ (1993) in press
Wassermann E, Murray RW, Yager WA, Trozzolo AM, Smolinsky G (1967) J Am Chem Soc 89: 5076
Itoh K (1967) Chem Phys Lett 1: 235
Schlenk W, Brauns M (1915) Ber Dtsch Chem Ges 48: 661: 669
Iwamura H (1987) Pure & Appl Chem 59: 1595 ibid 65: 57
Tyutyulkov N, Karabunarliev S (1986) Int J Quantum Chem 29: 1325
Veciana J, Vidal J, Jullian N (1989) Mol Cryst Liq Cryst 176: 443
Breslow R (1989) Mol Cryst Liq Cryst 176: 199
Coulson CA, Longuet-Higgins HC (1947) Proc R Soc Ser A 191: 39 and 192: 16
Dietz F, Müllen K, Baumgarten M, Tyutyulkov N (1993) Chem Phys in press
Even in: Buckminsterfullerene the highest spin state available is S = 1, although the neutral molecules is assumed to possess a threefold degenracy of the LUMO Baumgarten M, Gügel a, Gherghel L (1993) Adv Mater in press
Berson JA (1978) Acc Chem Res 11: 446
Berson JA (1987) Pure & Appl Chem 59: 1571
Tyutyulkov N, Karabunarliev S, Ivanov K (1989) Mol Cryst Liq Cryst 176: 139
Veciana (1989) Mol Cryst Liq Cryst 176: 75
Kirste B, Kurreck H, Lubitz W, Schubert K (1978) J Am Chem Soc 100: 2292
Kurreck H (1993) Angew Chem 105: 1472
Grimm M, Kirste B, Kurreck H (1986) Angew Chem 98: 1095 Int Ed Engl 25: 1097
Horn T, Baumgarten M, Gherghel L, Müllen K (1993) Tetrahedron Lett, 34: 5889
Longuet-Higgins HC (1950) J Chem Phys 18: 265
Klein DJ (1982) J Chem Phys 77: 3098
Itoh K (1978) Pure & Appl Chem 50: 1251
Dowd P, Chang W, Paik YH (1986) J Am Chem Soc 108: 7416
Du P, Borden WT (1987) J Am Chem Soc 109: 5284
Nash JJ, Dowd P, Jordan KD (1992) J Am Chem Soc 114: 10071
Nachtigall P, Jordan KD (1993) J Am Chem Soc 115: 270
Schmauss G, Baumgarte H, Zimmermann H (1965) Angew Chem Int Ed Engl 4: 596
Brickmann J, Kothe G (1973) J Chem Phys 59: 2807
Novak C, Kothe G, Zimmermann H (1974) Ber Bunsen-Ges 78: 265
Rajca A (1990) J Am Chem Soc 112: 5890
Nakamura N, Inoue K, Iwamura H, Fujioka, Sawaki Y (1992) J Am Chem Soc 114: 1484
Higuchi J (1963) J Chem Phys 38: 1237; ibid 39: 1847
Iwamura H (1986) Pure & Appl Chem 58: 187
Murata S, Iwamura H (1991) J Am Chem Soc 113: 5547
Baumgarten M, Müllen K, Tyutyulkov N, Madjarova G (1993) Chem Phys 169: 81
Tyutyulkov N, Ivanov Cl, Schopov I, Polansky OE, Olbrich G (1988) Int J Quantum Chem 34: 361
Yoshizawa K, Hatanaka M, Ito A, Tanaka K, Yamabe T (1993) Chem Phys Lett 202: 483
Ishida T, Iwamura H (1991) J Am Chem Soc 113, 4238–4241
Tanaka K, Yoshizawa K, Takata A, Yamabe T, Yamauchi J (1991) Synth Met 41–43: 3297
Mukai K, Nagai H, Ishizu K (1975) Bull Chem Soc Jpn 48: 2381
Calder A, Forrester AR, James PG, Luckhurst GR (1969) J Am Chem Soc 91: 3724
Yoshizawa K, Chano A, Ito A, Tanaka K, Yamabe T, Fujita H, Yamauchi J, Shiro M (1992) J Am Chem Soc 114: 5994
Yoshizawa J, Tanaka K, Yamabe T, Yamauchi J (1992) J Chem Phys 96: 5516
Torrance JB, Oostra S, Nazal A (1987) Synth Met 19: 809
Baumgarten M, Wehrmeister T, Karabunarliev S, Tyutyulkov N, Müllen K (1994) to be published
Wassermann E, Schueller K, Yager WA (1968) Chem Phys Lett 2: 259
Tukada H, Mutai K, Iwamura H (1987) J Chem Soc Chem Commun 1159
Matsumoto T, Ishida T, Ishida T, Koga N, Iwamura H (1992) J Am Chem Soc 114: 9952
Ling C, Minato M, Lahti PM, van Willigen H (1992) J Am Chem Soc 114: 9959
Dowd P (1966) J Am Chem Soc 88: 2587
Dowd P, Paik YH (1986) J Am Chem Soc 108: 2788
Jain R, Snyder GJ, Dougherty DA (1984) J Am Chem Soc 106: 7294
Novak JA, Jain R, Dougherty DA (1989) J Am Chem Soc 111: 7618
Dougherty DA, Jacobs SJ, Silverman SK, Murray MM, Shultz DA, West AP, Clites JA (1993) Mol cryst Liq Cryst in press
Fukutome H, Takahashi A, Ozaki Ma (1987) Chem Phys Lett 133: 34
Tukada H (1993) J Am Chem Soc in press
Müller U, Baumgarten M (1994) J Am Chem Soc submitted
Baumgarten M, Gherghel L, Gregorius H, Karabunarliev K, Müllen K (1993) to be published
Breslow R, Chang HW, Hill R, Wasserman E (1967) J Am Chem Soc 89: 1112
Wassermann E, Hutton RS, Kuck VJ, Chandross EA (1974) J Am Chem Soc 96: 1965
Saunders M, Berger R, Jaffe A, McBride JM, O'Neill J, Breslow R, Hoffman JM, Perchonock C, Wassermann E, Hutton RS, Kuck VJ (1973) J Am Chem Soc 95: 3017
Breslow R, Maslak P, Thomaides J (1984) J Am Chem Soc 106: 6453
Breslow R, Hill R, Wassermann E (1964) J Am Chem Soc 86: 5349
Fukunaga T (1976) J Am Chem Soc 98: 610
Veciana J, Rovira C, Ventosa N, Crespo MI, Palacio F (1993) J Am Chem Soc 115: 57
Hoshino M, Kimura K, Imamura M (1973) Chem Phys Lett 20: 193
Tukada H (1991) J Am Chem Soc 113: 8991
Tukada H, Mutai K (1993) Tetrahedron Lett in press
Rajca A, Utamapanya (1992) J Org Chem 47: 1760
Dougherty DA, Kaisaki DA (1990) Mol Cryst Liq Cryst 183: 71
Nakamura N, Inoue K, Iwamura H (1992) J Am Chem Soc 114: 1484
Nakamura N, Inoue K, Iwamura H (1993) Angew Chem 105: 900
Rajca A, Utamapanya S, Thayumanavan S (1992) J Am Chem Soc 114: 1884
Miller JS (1992) Adv Mater 4: 298; ibid 435
Winter H, Gotoschy B, Dormann E, Naarmann H (1990) Synth Met 341–352
Cosmo R, Dormann E, Gotschy B, Naarmann H, Winter H (1991) Synth Met 41–43: 369
Cosmo R, Naarmann H (1990) Mol Cryst Liq Cryst 185: 89
Yoshioka N, Nishide H, Tsuchida E (1990) Mol Cryst Liq Cryst 190: 45
Nishide H, Yoshioka N, Kaneko T, Tsuchida E (1990) Macromolecules 23: 4487
Iwamura H, McKelvey RD (1988) Makromolecules 21: 3386
Fujii A, Ishida T, Koga N, Iwamura H (1991) Macromolecules 24: 1077
Iwamura H, Murata S (1989) Mol Cryst Liq Cryst 176: 33
Wegner G (1977) Pure & Appl Chem 49: 443
Wegner G (1979) in: Hartfield EW (ed) Molecular metals. Plenum Press, NY, p 209
Korshak YV, Madvedeva TV, Ovchinnikov AA, Spector VN (1987) Nature 326: 370
Zhang JH, Epstein AJ, Miller JS, O'Connor CJ (1989) Mol Cryst Liq Cryst 176: 271
Cao Y, Wang P, Hu Z, Li S, Zhang L, Zhao J (1988) Solid State Commun 68: 817
Wiley DW, Calabrese JC, Miller JS (1989) Mol Cryst Liq Cryst 176: 277
Inoue K, Koga N, Iwamura H (1991) J Am Chem Soc 113: 9803
Inoue K, Iwamura H (1992) Adv Mater 4: 801
Awaga K, Sugano T, Kinoshita M (1986) J Chem Phys 85: 2211
Harrer W, Kurreck H, Reusch J, Gierke W (1975) Tetrahedron 31: 625
Shiomi D, Tamura M, Sawa H, Kato R, Kinoshita M (1993) Synth Met 1993 in press
Awaga K, Maruyama Y (1989) Chem Phys Lett 158: 556
Turek P, Nozawa K, Shiomi D, Awaga D, Awaga K, Inabe T, Maruyama Y, Kinoshita M (1991) Chem Phys Lett 180: 327
Kinoshita M, Turek P, Tamura M, Nozawa K, Shiomi D, Nakazawa Y, Ishikawa M, Takahashi M, Awaga K, Inabe T, Maruyama Y (1991) Chem Lett 1225
Chiang LY, Goshorn DP (1989) Mol Cryst Liq Cryst 176: 229
Miller JS, Epstein AJ (1989) Mol Cryst Liq Cryst 176: 347
Miller JS, Calabrese JC, Harlow RL, Dixon DA, Zhang JH, Reiff WM, Chittipaldi S, Selover MA, Epstein AJ (1990) J Am Chem Soc 112: 5496
Epstein AJ, Miller JS (1993) Proceedings of Electrical and related properties or organic solids. Capri I, (1992) Mol Cryst Liq Cryst 228: 99
Cannon RD (1980) “Electron Transfer Reactions”, Butterworth, London
Paddon-Row MN, Jordan KD (1988) In: Liebman JF, Greenberg A (eds) Modern models of bonding and delocalization, chap 3. VCH Publishers, New York
Marcus RA (1956) J Chem Phys 24: 979
Marcus RA (1965) J Chem Phys 43: 679
Closs G, Miller JR (1988) Science 240, 440
Santamaria J (1988) In: Fox MA, Cannon M (eds) Photoinduced electron transfer. Elsevier, Amsterdam
Grampp G, Jaenicke W (1984) Ber Bunsenges Phys Chem 88: 325; ibid 88: 335
Gerson F, Kowert B, Peake PM (1974) J Am Chem Soc 96: 118
Kuznetsov AM, Ulstrup J, Vorotyntsev MA (1988) Solvent effects in charge transfer processes. In: Dogonadze RR, Kalman E, Kornyshev AA, Ulstrup J (eds) The chemical physics of solvation. Studies in physical and theoretical chemistry, vol 38, chap 3, Elsevier, Amsterdam
Gerson F, Wellauer T, Oliver AM, Paddon-Row MN (1990) Helv Chim Acta 73: 1586
Liang N, Miller JR, Closs GL (1990) J Am Chem soc 112: 5353
Jordan KD, Paddon-Row MN (1992) Chem Rev 92: 395
Kochi JK (1988) Angew Chem 100: 1331; Int Ed Engl 27: 1227
Wasielewski MR (1992) Chem Rev 92: 435
Baumgarten M, Müllen K (1992) AIP Conf Proc; St. Thomas, Virgin Islands 262: 68–76
Hopfield J, Onuchic JN, Beratan DN (1988) Science 214: 817
Mehring M (1989) In: Kuzmany H, Mehring M, Roth S (eds) Electronic properties of conjugated polymers III. Springer, Berlin Heidelberg New York, p 242
Aviram A (1988) J Am Chem Soc 110: 5687
Joachim C, Launay JP (1990) J Mol Electronics 6: 37
Aviram A, Ratner MA (1974) Chem Phys Lett 29: 277
Aviram A, Seiden PE, Ratner MA (1982) In: Carter FL (ed) Molecular electronic devices. Marcel Dekker, New York, p 5
Metzger RM, Panetta CA, Miura Y, Torres (1987) Synth Met 18: 787
Torres E, Panetta CA, Metzger RM (1987) J Org Chem 52: 2944 (1987)
Metzger RM, Panetta CA (1991) New J Chem 15: 209
Binnig G, Rohrer H, Gerber Ch, Weibl E (1982) Phys Rev Lett 49: 57
Roberts GG (ed) (1990) “Langmuir Blodgett Films” Plenum Press, New York
Sariciftci NS, Neugebauer H, Mehring M (1991) Synth Met 41–43: 2971
Burroughes JH, Friend RH (1991) In: Brédas JL, Silbey R (eds), Conjugated polymers. Kluwer, Dordrecht, p 555
Kmetz AR, Willisen FK (1976) Non-emissive electrooptic displays. Plenum, New York
Inganas O, Lundström I (1987) Synth Met 21: 13
Inganas O, Lundström I, Skotheim TA (1986) In: Skotheim TA (ed) Handbook of conducting polymers. Marcel Dekker, New York, p 524
Friend RH (1992) Synth Met 51: 357
Yoneyama H, Wakamato K, Tamura H (1985) J Electrochem Soc 132: 2414
Yosino K, Kaneto K, Inuishi Y (1983) Jpn J Appl Phys 22: L157
Kobayashi T, Yoneyama H, Tamura H (1984) J Elektroanal Chem 177: 281
LaCroix JC, Kanazawa KK, Diaz AF (1989) J Electrochem Soc 136: 1308
Wolf JF, Miller GG, Shacklette, Elsenbaumer RL, Baughman RH US Patent 4, 893, 908
Braun D, Heeger AJ (1991) Appl Phys Lett 58: 1982
Adachi C, Tsutsui T, Saito S (1993) Appl Phys
Grem G, Leditzky G, Ulrich B, Leising G (1992) Adv Mater 4: 36
Holmes AB (1992) Nature 356: 47
Heeger AJ (1992) Nature 357: 477
Reimers JR, Hush NS (1990) Inorg Chem 29: 3886
Joachim C, Launay JP, Woitellier S (1990) Chem Phys 147: 131
Heine B, Sigmund E, Maier S, Port H, Wolff HC, Effenberger F, Schlosser H (1990) J Molec Electronics 6: 51
Yao H, Okada T, Mataga N (1989) J Phys Chem 93: 7388
Rettig W (1986) Angew. Chemie 98: 969; Int. Ed. Engl 125: 971
Lippert E, Lüder W, Boos H (1962) In: Mangini A (ed) Adv in molecular spectroscopy. Pergamon, Oxford, p 443
Bonacic-Koutecky V, Koutecky J, Michl J (1987) Angew Chem 99: 216, Int. Ed. Engl 26: 218
Rettig W (1991) Nachr Chem Tech Lab 39: 398406
Barbara PF, Jarzeba W (1988) Acc Chem Res 21: 195
Mataga N, Yao H, Okada T, Rettig W (1989) J Phys Chem 93: 3383–86
Fritz R, Rettig W, Müller U, Müllen K (1994) (to be published)
Dobkowski J, Rettig W, Paeplow B, Koch KH, Müllen K, Lapouyade R, Grabowski ZR (1994) J Am Chem Soc in press
Haarer D, Blumen A (1988) Angew Chem 100: 1252; Int Ed Engl 27: 1210
Hoegl H, Sus O, Neugebauer W (1962) US Pat 3 037 861
Shattuk DM, Vahtra U (1969) US Pat 3 484 237
Abkowitz M, Bässler H, Stolka M (1991) Phil Mag B 63: 201
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Baumgarten, M., Müllen, K. (1994). Radical ions: Where organic chemistry meets materials sciences. In: Mattay, J. (eds) Electron Transfer I. Topics in Current Chemistry, vol 169. Springer, Berlin, Heidelberg. https://doi.org/10.1007/3-540-57565-0_74
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