Self-association and electron transfer in donor-acceptor dyads connected by meta-substituted oligomers

Journal of the American Chemical Society

Volumn 131, Issue 34, 2009, Pages 12218-12229

  Molina Ontoria, Agustín ^a   Fernández, Gustavo ^a   Wielopolski, Mateusz ^b   Atienza, Carmen ^b   Sánchez, Luis ^a   Gouloumis, Andreas ^a   Clark, Timothy ^b   Martín, Nazario ^a,c   Guldi, Dirk M ^b  

^a UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

^b UNIVERSITY OF ERLANGEN NUREMBERG   (Germany)

^c INSTITUTO MADRILEÑO DE ESTUDIOS AVANZADOS EN NANOCIENCIA IMDEA NANOCIENCIA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

AFM; AROMATIC RINGS; ASSOCIATION CONSTANT; BINDING STRENGTH; CONCENTRATION-DEPENDENT; DONOR-ACCEPTOR DYADS; ELECTROACTIVE; ELECTRON ACCEPTOR; ELECTRON DONOR ACCEPTORS; ELECTRON DONORS; ELECTRON TRANSFER; GASPHASE; HIGH CONCENTRATION; INTRA-MOLECULAR ELECTRON TRANSFER; INTRACOMPLEX ELECTRON TRANSFER; LOW CONCENTRATIONS; MALDI-TOF; MICA SURFACES; NEW SERIES; PHENYLENE SPACERS; PHENYLENEETHYNYLENE; PHOTOACTIVITY; PHOTOPHYSICAL EXPERIMENT; RADICAL ION PAIRS; SELF-ASSOCIATIONS; SPACER LENGTHS; TETRATHIAFULVALENES; VARIABLE LENGTH; VARIABLE TEMPERATURE; WIRELIKE STRUCTURES;

AROMATIC COMPOUNDS; ASSOCIATION REACTIONS; CONCENTRATION (PROCESS); ELECTRON TRANSITIONS; EXCITED STATES; FREE RADICAL REACTIONS; GAS ABSORPTION; MICA; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OLIGOMERS; SILICATE MINERALS;

LEAD;

CARBON; COPPER; FUNCTIONAL GROUP; ION; MICA; OLIGOMER; PALLADIUM; PROTON; TETRATHIAFULVALENE DERIVATIVE;

ARTICLE; ATOMIC FORCE MICROSCOPY; BINDING AFFINITY; CHEMICAL BINDING; CHEMICAL BOND; CHEMICAL INTERACTION; CHEMICAL STRUCTURE; CONCENTRATION (PARAMETERS); CONJUGATE; CYCLIC POTENTIOMETRY; DIFFERENTIAL PULSE VOLTAMMETRY; ELECTRON; ELECTRON TRANSPORT; FLUORESCENCE; GAS; HYBRID; INFRARED SPECTROSCOPY; LIGHT ABSORPTION; MATRIX ASSISTED LASER DESORPTION IONIZATION TIME OF FLIGHT MASS SPECTROMETRY; OXIDATION REDUCTION REACTION; PHOTOREACTIVITY; PHYSICAL CHEMISTRY; PROTON NUCLEAR MAGNETIC RESONANCE; SONOGASHIRA REACTION; SUBSTITUTION REACTION; SYNTHESIS;

EID: 69349084631     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9024269     Document Type: Article

References (95)

1. (a) Special Issue on Organic Electronics. Chem. Mater. 2004, 16, 4381-4846.
2. (b) Wassel, R. A.; Gorman, C. B. Angew. Chem., Int. Ed. 2004, 43, 5120-5123.
3. (c) Carroll, R. L.; Gorman, C. B. Angew. Chem., Int. Ed. 2002, 41, 4378-4400.
4. (d) Tour, J. M. Acc. Chem. Res. 2000, 33, 791-804.
5. For recent reviews on PV cells, see: (a) Brabec, C. J.; Sariciftci, N. S.; Hummelen, J. C. Adv. Funct. Mater. 2001, 11, 15-26.
6. (b) Coakley, K. M.; McGehee, M. D. Chem. Mater. 2004, 16, 4533-4542.
7. (c) Günes, S.; Neugebauer, H. Chem. Rev. 2007, 107, 1324-1338.
8. (d) Thompson, B. C.; Fréchet, J. M. J. Angew. Chem., Int. Ed. 2008, 47, 58-77.
9. For reviews, see: (a) Wasielewski, M. R. Chem. Rev. 1992, 92, 435-461.
10. (b) Sánchez, L.; Martín, N.; Guldi, D. M. Angew. Chem., Int. Ed. 2005, 44, 5374-5382.
11. (c) D'Souza, F.; Ito, O. Coord. Chem. Rev. 2005, 249, 1410-1422.
12. (d) Kawase, T.; Kurata, H. Chem. Rev. 2006, 106, 5250-5273.
13. (e) Wasielewski, M. R. J. Org. Chem. 2006, 71, 5051-5066.
14. (f) Pérez, E. M.; Martín, N. Chem. Soc. Rev. 2008, 37, 1512-1519.
15. (a) Elias, B.; Genereux, J. C.; Barton, J. K. Angew. Chem., Int. Ed. 2008, 47, 9067-9070.
16. (b) Giese, B. Bioorg. Med. Chem. 2006, 14, 6139-6143.
17. (c) Conwell, E. M. Proc. Natl. Acad. Sci. U.S.A. 2005, 102, 8795-8799.
18. (d) Mynar, J. L.; Yamamoto, T.; Kosaka, A.; Fukushima, T.; Ishii, N.; Aida, T. J. Am. Chem. Soc. 2008, 130, 1530-1531.
19. (e) Yamamoto, Y.; Fukushima, T.; Suna, Y.; Ishii, N.; Saeki, A.; Seki, S.; Tagawa, S.; Taniguchi, M.; Kawai, T.; Aida, T. Science 2006, 314, 1761-1764.
20. (a) González-Rodríguez, D.; Torres, T.; Olmstead, M. M.; Rivera, J.; Herranz, M. A.; Echegoyen, L.; Atienza Castellanos, C.; Guldi, D. M. J. Am. Chem. Soc. 2006, 128, 10680-10681.
21. (b) Jeon, W. S.; Moon, K.; Park, S. H.; Chun, H.; Ko, Y. H.; Lee, J. Y.; Lee, E. S.; Samal, S.; Selvapalam, N.; Rekharsky, M. V.; Sindelar, V.; Sobransingh, D.; Inoue, Y.; Kaifer, A. E.; Kim, K. J. Am. Chem. Soc. 2005, 127, 12984-12989.
22. (a) D'Souza, F.; Chitta, R.; Sandanayaka, A. S. D.; Subbaiyan, N. K.; D'Souza, L.; Araki, Y.; Ito, O. J. Am. Chem. Soc. 2007, 129, 15865-15871.
23. (b) Li, W.-S.; Kim, K. S.; Jiang, D.-L.; Tanaka, H.; Kawai, T.; Kwon, J. H.; Kim, D.; Aida, T. J. Am. Chem. Soc. 2006, 128, 10527-10532.
24. (c) Imahori, H.; Sekiguchi, Y.; Kashiwagi, Y.; Sato, T.; Araki, Y.; Ito, O.; Yamada, H.; Fukuzumi, S. Chem. - Eur. J. 2004, 10, 3184-3196.
25. (d) Jiang, D.-L.; Choi, C.-K.; Honda, K.; Li, W.-S.; Yuzawa, T.; Aida, T. J. Am. Chem. Soc. 2004, 126, 12084-12089.
26. (a) Zhang, R.; Wang, Z.; Wu, Y.; Fu, H.; Yao, J. Org. Lett. 2008, 10, 3065-3068.
27. (b) Beckers, E. H. A.; Meskers, S. C. J.; Schenning, A. P. H. J.; Chen, Z.; Würthner, F.; Marsal, P.; Beljonne, D.; Cornil, J.; Janssen, R. A. J. J. Am. Chem. Soc. 2006, 128, 649-657.
28. (c) Marcos Ramos, A.; Meskers, S. C. J.; Beckers, E. H. A.; Prince, R. B.; Brunsveld, L.; Janssen, R. A. J. J. Am. Chem. Soc. 2004, 126, 9630-9644.
29. (a) Yamashita, Y.; Kobayashi, Y.; Miyashi, T. Angew. Chem., Int. Ed. Engl. 1989, 28, 1052-1053.
30. (b) Bryce, M. R.; Moore, A. J.; Hasan, M.; Ashwell, G. J.; Fraser, A. T.; Clegg, W.; Hursthouse, M. B.; Karaulov, A. I. Angew. Chem., Int. Ed. Engl. 1990, 29, 1450-1452.
31. (c) Martín, N.; Sánchez, L.; Seoane, C.; Ortí, E.; Viruela, P. M. J. Org. Chem. 1998, 63, 1268-1279.
32. (d) Segura, J. L.; Martín, N. Angew. Chem., Int. Ed. 2001, 40, 1372-1409.
33. (a) Echegoyen, L.; Echegoyen, L. E. Acc. Chem. Res. 1998, 31, 593-601.
34. (b) Guldi, D. M.; Prato, M. Acc. Chem. Res. 2000, 33, 695-703.
35. (c) Guldi, D. M. Chem. Commun. 2000, 321-327.
36. (d) Martín, N. Chem. Commun. 2006, 2093-2104.
37. Martín, N.; Sánchez, L.; Herranz, M. A.; Illescas, B. M.; Guldi, D. M. Acc. Chem. Res. 2007, 40, 1015-1024.
38. (a) Pérez, E. M.; Sánchez, L.; Fernández, G.; Martín, N. J. Am. Chem. Soc. 2006, 128, 7172-7173.
39. (b) Pérez, E. M.; Sierra, M.; Sánchez, L.; Torres, M. R.; Viruela, R.; Viruela, P. M.; Ortí, E.; Martín, N. Angew. Chem., Int. Ed. 2007, 46, 1847-1851.
40. (c) Fernández, G.; Pérez, E. M.; Sánchez, L.; Martín, N. Angew Chem., Int. Ed. 2008, 47, 1094-1097.
41. (d) Fernández, G.; Pérez, E. M.; Sánchez, L.; Martín, N. J. Am. Chem. Soc. 2008, 130, 2410-2411.
42. (e) Fernández, G.; Sánchez, L.; Pérez, E. M.; Martín, N. J. Am. Chem. Soc. 2008, 130, 10674-10683.
43. Gayathri, S. S.; Wielopolski, M.; Pérez, E. M.; Fernández, G.; Sánchez, L.; Viruela, R.; Ortí, E.; Guldi, D. M.; Martín, N. Angew. Chem., Int. Ed. 2009, 48, 815-819.
44. (a) Thompson, A. L.; Ahn, T.-S.; Thomas, K. R. J.; Thayumanavan, S.; Martinez, T. J.; Bardeen, C. J. J. Am. Chem. Soc. 2005, 127, 16348-16349.
45. (b) Gaab, K. M.; Thompson, A. L.; Xu, J.; Martinez, T. J.; Bardeen, C. J. J. Am. Chem. Soc. 2003, 125, 9288-9289.
46. (a) Nelson, J. C.; Saven, J. G.; Moore, J. S.; Wolynes, P. G. Science 1997, 277, 1793-1796.
47. (b) Prince, R. B.; Saven, J. G.; Moore, J. S.; Wolynes, P. G. J. Am. Chem. Soc. 1999, 121, 3114-3121.
48. (c) Lahiri, S.; Thompson, J. L.; Moore, J. S. J. Am. Chem. Soc. 2000, 122, 11315-11319.
49. (a) Wielopolski, M.; Atienza, C.; Clark, T.; Guldi, D. M.; Martín, N. Chem. - Eur. J. 2008, 14, 6379-6390.
50. (b) Figueira-Duarte, T. M.; Gégout, A.; Nierengarten, J. F. Chem. Commun. 2007, 109-119.
51. (c) Atienza, C.; Martín, N.; Wielopolski, M.; Haworth, N.; Clark, T.; Guldi, D. M. Chem. Commun. 2006, 3202-3204.
52. (a) Sonogashira, K. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, U.K., 1991.
53. (b) Sonogashira, K. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, Germany, 1998.
54. (c) Sonogashira, K. J. Organomet. Chem. 2002, 653, 46-49.
55. (d) Eisler, S.; Chahal, N.; McDonald, R.; Tykwinski, R. R. Chem. - Eur. J. 2003, 9, 2542-2550.
56. (e) Mohr, W.; Stahl, J.; Hampel, F.; Galysz, J. A. Chem. - Eur. J. 2003, 9, 3324-3340.
57. (f) Eisler, S.; Slepkov, A. D.; Elliott, E.; Luu, T.; McDonald, R.; Hegmann, F. A.; Tykwinski, R. R. J. Am. Chem. Soc. 2005, 127, 2666-2676.
58. Vidal-Ferran, A.; Müller, C. M.; Sanders, J. K. M. J. Chem. Soc., Chem. Commun. 1994, 2657-2658.
59. Grave, C.; Lentz, D.; Schafer, A.; Samorí, P.; Rabe, J. P.; Franke, P.; Schluter, A. D. J. Am. Chem. Soc. 2003, 125, 6907-6918.
60. Wagner, R. W.; Johnson, T. E.; Li, F.; Lindsey, J. S. J. Org. Chem. 1995, 60, 5266-5273.
61. Díaz, M. C.; Illescas, B. M.; Seoane, C.; Martín, N. J. Org. Chem. 2004, 69, 4492-4499.
62. (a) Maggini, M.; Scorrano, G.; Prato, M. J. Am. Chem. Soc. 1993, 115, 9798-9799.
63. (b) Tagmatarchis, N.; Prato, M. Synlett 2003, 768-779.
64. (a) Bryce, M. R.; Moore, A. J. J. Chem. Soc., Perkin Trans. 1 1991, 157-168.
65. (b) Bryce, M. R.; Moore, A. J. J. Chem. Soc., Chem. Commun. 1991, 22, 1638-1639.
66. (c) Batsanov, A. S.; Bryce, M. R.; Coffin, M. A.; Green, A.; Hester, R. E.; Howard, J. A. K.; Lednev, I. K.; Martín, N.; Moore, A. J.; Moore, J. N.; Ortí, E.; Sánchez, L.; Savirón, M.; Viruela, P. M.; Viruela, R.; Ye, T. Chem. - Eur. J. 1998, 4, 2580-2592.
67. We and others have experimentally observed that the oxidation processes of π-conjugated oligomers sometimes appear as broad and difficultly assignable waves in cyclic voltammetry. For recent examples, see: (a) Fernández, G.; Sánchez, L.; Veldman, D.; Wienk, M. M.; Atienza, C.; Guldi, D. M.; Janssen, R. A. J.; Martín, N. J. Org. Chem. 2008, 73, 3189-3196.
68. (b) Zen, A.; Bilge, A.; Galbrecht, F.; Alle, R.; Meerholz, K.; Grenzer, J.; Neher, D.; Scherf, U.; Farrell, T. J. Am. Chem. Soc. 2006, 128, 3914-3915.
69. (c) Narutaki, M.; Takimiya, K.; Otsubo, T.; Harima, Y.; Zhang, H.; Araki, Y.; Ito, O. J. Org. Chem. 2006, 71, 1761-1768.
70. (d) Zhao, Y.; Shirai, Y.; Slepkov, A. D.; Cheng, L.; Alemany, L. B.; Sasaki, T.; Hegmann, F. A.; Tour, J. M. Chem. - Eur. J. 2005, 11, 3643-3658.
71. A subsequent MALDI-TOF analysis carried out for the para-conjugated congener of dyad 5, compound 9a in ref 6c, has also allowed the observation of this unexpected behavior.
72. The ability of a pristine exTTF molecule to recognize [60]fullerene or its derivative PCBM has been proven to be negligible: Otero, R.; É cija, D.; Fernández, G.; Gallego, J. M.; Sánchez, L.; Martín, N.; Miranda, R. Nano Lett. 2007, 7, 2602-2607.
73. The travel time in MALDI-TOF experiments is directly proportional to the m/z value. Therefore, the ions corresponding to the aggregates formed from 16 need a longer time to reach the detector in comparison with the other conjugates, and they hold a higher possibility to disassemble. For a recent book on the utilization of the MALDI-TOF technique to detect supramolecular species, see: Schalley, C. Analytical Methods in Supramolecular Chemistry; Wiley: New York, 2007.
74. (a) Pérez, E. M.; Capodilupo, A. L.; Fernández, G.; Sánchez, L.; Viruela, P. M.; Viruela, R.; Ortí, E.; Bietti, M.; Martín, N. Chem. Commun. 2008, 4567-4569.
75. -1.
76. Lukoyanova, O.; Kitaygorodskiy, A.; Cardona, C. M.; Echegoyen, L. Chem. - Eur. J. 2007, 13, 8294-8301.
77. (a) Giacalone, F.; Segura, J. L.; Martín, N.; Guldi, D. M. J. Am. Chem. Soc. 2004, 126, 5340-5341.
78. (b) de la Torre, G.; Giacalone, F.; Segura, J. L.; Martín, N.; Guldi, D. M. Chem. Eur. J. 2005, 11, 1267-1280.
79. Guldi, D. M.; Scheloske, M.; Dietel, E.; Hirsch, A.; Troisi, A.; Zerbetto, F.; Prato, M. Chem. - Eur. J. 2003, 9, 4968-4979.
80. 60 with a 1:1 complex stoichiometry. The complex formation is associated with a newly developing charge transfer absorption, whose equilibrium is expressed by the Benesi-Hildebrand method. To this end, we have used the concentration dependence to determine the association constant according to Benesi-Hildebrand: Benesi, H. A.; Hildebrand, J. H. J. Am. Chem. Soc. 1949, 71, 2703-2707.
81. -1) combined with appreciable absorption changes, this method provides reasonable results: Yang, C.; Liu, L.; Mu, T.-W.; Guo, Q.-X. Anal. Sci. 2000, 16, 537-540.
82. In turn, it has emerged as a versatile tool for describing the 1:1 association of organic charge transfer complexes. Organic Charge-Transfer Complexes; Foster, R., Ed.; Academic Press: London, 1969; p 125.
83. (a) Guldi, D. M. Pure Appl. Chem. 2003, 75, 1069-1076.
84. (b) Guldi, D. M. Chem. Soc. Rev. 2002, 31, 22-36.
85. Herranz, M. A.; Ehli, C.; Campidelli, S.; Gutiérrez, M.; Hug, G. L.; Ohkubo, K.; Fukuzumi, S.; Prato, M.; Martín, N.; Guldi, D. M. J. Am. Chem. Soc., 2008, 130, 66-73.
86. Schuster, D. I.; MacMahon, S.; Guldi, D. M.; Echegoyen, L.; Braslavsky, S. E. Tetrahedron 2006, 62, 1928-1936.
87. (a) Guldi, D. M.; Hungerbühler, H.; Asmus, K.-D. J. Phys. Chem. 1995, 99, 9380-9385.
88. (b) Guldi, D. M.; Sánchez, L.; Martín, N. J. Phys. Chem. B 2001, 105, 7139-7144.
89. (a) Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5653.
90. (b) Burke, K.; Perdew, J. P.; Wang, Y. In Electronic Density Functional Theory: Recent Progress and New Directions; Dobson, J. F., Vignale, G., Das, M. P., Eds.; Plenum: New York, 1998.
91. (a) Ditchfield, R.; Hehre, W. J.; Pople, J. A. J. Chem. Phys. 1971, 54, 724-728.
92. (b) Rassolov, V. A.; Pople, J. A.; Ratner, M. A.; Windus, T. L. J. Chem. Phys. 1998, 109, 1223-1226.
93. All DFT calculations were performed using the Gaussian 03 program package: Frisch, M. J.; et al. Gaussian 03, revision D.02; Gaussian, Inc.: Wallingford, CT, 2004.
94. Winget, P.; Horn, A. H. C.; Selcuki, C.; Martin, B.; Clark, T. J. Mol. Model. 2003, 9, 408-414.
95. Rauhut, G.; Clark, T.; Steinke, T. J. Am. Chem. Soc. 1993, 115, 9174-9181.