Torsional influences within disordered organic electronic materials based upon non-benzenoid 1,6-methano[10]annulene rings

Macromolecules

Volumn 45, Issue 18, 2012, Pages 7339-7349

  Streifel, Benjamin C ^a   Peart, Patricia A ^b,c   Martínez Hardigree, Josué F ^b   Katz, Howard E ^a,b   Tovar, John D ^a,b  

^a JOHNS HOPKINS UNIVERSITY   (United States)

^b Johns Hopkins University   (United States)

^c DOW CHEMICAL COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 ,1 ,3-BENZOTHIADIAZOLE; ALKYL CHAIN; ANNULENE RINGS; ANNULENES; AROMATIC RINGS; AROMATIC SUB-UNITS; CONJUGATED MATERIALS; DIKETOPYRROLOPYRROLES; DONOR-ACCEPTOR POLYMERS; EFFECTIVE CONJUGATION LENGTH; ELECTRON COMPONENT; ELECTRON DONORS; MODEL SYSTEM; ORGANIC ELECTRONIC MATERIALS; ORGANIC ELECTRONICS; POLYMER BACKBONES; REGIOISOMERS; SMALL MOLECULES; TORSIONAL STRAIN;

AROMATIZATION; ELECTRONIC PROPERTIES; MOLECULES; PHOTOLUMINESCENCE SPECTROSCOPY; SYNTHESIS (CHEMICAL); THIOPHENE;

AROMATIC POLYMERS;

EID: 84866714150     PISSN: 00249297     EISSN: None     Source Type: Journal    
DOI: 10.1021/ma301408w     Document Type: Article

References (51)

1. Zhokhavets, U.; Erb, T.; Hoppe, H.; Gobsch, G.; Sariciftci, N. S. Thin Solid Films 2006, 496, 679
2. Sivula, K.; Luscombe, C. K.; Thompson, B. C.; Frechét, J. M. J. J. Am. Chem. Soc. 2006, 128, 13988
3. Brabec, C. J. Sol. Energy Mater. Sol. Cells 2004, 83, 273
4. Yip, H.-L.; Jen, A. K.-Y. Energy Environ. Sci. 2012, 5, 5994
5. Chen, T.-A.; Rieke, R. D. Synth. Met. 1993, 60, 175
6. Chen, T.-A.; Wu, X.; Rieke, R. D. J. Am. Chem. Soc. 1995, 117, 233
7. McCullough, R. D.; Tristram-Nagle, S.; Williams, S. P.; Lowe, R. D.; Jayaraman, M. J. Am. Chem. Soc. 1993, 115, 4910
8. McCullough, R. D.; Lowe, R. D. J. Chem. Soc., Chem. Commun. 1992, 70
9. McCullough, R. D.; Williams, S. P.; Tristram-Nagle, S.; Jayaraman, M.; Eqbank, P. C.; Miller, L. Synth. Met. 1995, 69, 279
10. McCullough, R. D.; Lowe, R. D.; Jayaraman, M.; Anderson, D. L. J. Org. Chem. 1993, 58, 904-912
11. Woo, C. H.; Thompson, B. C.; Bumjoon, J. K.; Toney, M. F.; Frechet, J. M. J. J. Am. Chem. Soc. 2008, 130, 16324
12. Jayakannan, M.; Van Hal, P. A.; Janssen, R. A. J. J. Polym Sci., Part A: Polym. Chem. 2002, 40, 251
13. Mondal, R.; Ko, S.; Verploegen, E.; Becerril, H. A.; Toney, M. F.; Bao, Z. J. Mater. Chem. 2011, 21, 1537
14. Ding, J.; Li, Z.; Cui, Z.; Robertson, G. P.; Song, N.; Du, X.; Scoles, L. J. Polym Sci., Part A: Polym. Chem. 2011, 49, 3374
15. Lee, S. K.; Cho, S.; Tong, M.; Seo, J. H.; Heeger, A. J. J. Polym. Sci., Part A: Polym. Chem. 2011, 49, 1821
16. Elsenbaumer, R. L.; Jen, K.-Y.;; Miller, G. G.; Eckhardt, H.; Shacklette, L. W.;; Jow, R. In Electronic Properties of Conjugated Polymers; Kuzmany, H.; Mehring, M.; Roth, S., Eds.; Springer Series in Solid State Sciences; Springer: Berlin, 1987; Vol. 76, p 400.
17. Souto-Maior, R. M.; Hinkelmann, K.; Wudl, F. Macromolecules 1990, 23, 1268
18. Zagorska, M.; Kulszewicz-Bajer, I.; Pron, A.; Firlcj, L.; Berier, P.; Galtier, G. Synth. Met. 1991, 45, 385
19. Zagorska, M.; Krishe, B. Polymer 1990, 31, 1379
20. Krishe, B.; Hellberg, J.; Lilja, C. J. Chem. Soc., Chem. Commun. 1987, 19, 1476
21. An excellent review of poly(3-alkylthiophene) regioregularity is found in the following: McCullough, R. D. Adv. Mater. 1998, 10, 93
22. Hong, S. Y.; Kim, C. Y.; Kim, D. Y.; Hoffman, R. Macromolecules 2001, 34, 6475
23. Havinga, E. E.; ten Hoeve, W.; Wynberg, H. Polym. Bull. 1992, 29, 119
24. Havinga, E. E.; ten Hoeve, W.; Wynberg, H. Synth. Met. 1993, 55-57, 299
25. Peart, P. A.; Tovar, J. D. Org. Lett. 2007, 9, 3041
26. Peart, P. A.; Repka, L. M.; Tovar, J. D. Eur. J. Org. Chem. 2008, 2193
27. Peart, P. A.; Tovar, J. D. Macromolecules 2009, 42, 4449
28. Peart, P. A.; Elbaz, G.; Tovar, J. D. Pure Appl. Chem. 2010, 82, 1045
29. Vogel, E.; Roth, H. D. Angew. Chem. 1964, 76, 145
30. Hummelen, J. C.; Knight, B. W.; LePeq, F.; Wudl, F.; Wilkins, C. J. Org. Chem. 1995, 60, 532-538
31. Sirringhaus, H. Adv. Mater. 2005, 17, 2411
32. Baek, N. S.; Hau, S. K.; Yip, H.-L.; Acton, O.; Chen, K.-S.; Jen, A. K.-Y. Chem. Mater. 2008, 20, 5734
33. Osaka, I.; Zhang, R.; Sauvé, G.; Smilgies, D.-M.; Kowalewski, T.; McCullough, R. D. J. Am. Chem. Soc. 2009, 131, 2521
34. Bryant-Friedrich, A. C.; Neidlein, R. Helv. Chim. Acta 1997, 80, 128
35. Bryant-Friedrich, A. C.; Neidlein, R. Helv. Chim. Acta 1997, 80, 1639
36. Mee, S. P. H.; Lee, V.; Baldwin, J. E. Angew. Chem., Int. Ed. 2004, 43, 1132
37. Karikomi, M.; Kitamura, C.; Tanaka, S.; Yamashita, Y. J. Am. Chem. Soc. 1995, 117, 6791-6792
38. Bijleveld, J. C.; Zoombelt, A. P.; Mathijssen, S. G. J.; Wienk, M. M.; Turbiex, M.; de Leeuw, D. M.; Janssen, R. A. J. J. Am. Chem. Soc. 2009, 131, 16616
39. Woo, C. H.; Beaujuge, P. M.; Holcombe, T. W.; Lee, O. P.; Fréchet, J. M. J. J. Am. Chem. Soc. 2010, 132, 15547
40. Holdcroft, S. J. Polym. Sci., Part B: Polym. Phys. 1991, 29, 1585-1588
41. Wohlgenannt, M.; Jiamng, X. M.; Vardeny, Z. V. Phys. Rev. B 2004, 69, 241204(R)
42. Brédas, J. L. J. Chem. Phys. 1985, 82, 3809
43. McCullough, R. D. Adv. Mater. 1998, 10, 93
44. A reviewer suggested an alternative explanation whereby the similarity in PL wavelengths in the polymers with stronger acceptors could originate from twisted intramolecular charge transfer (TICT) states (Grabowski, A. R.; Rotkiewicz, K. Chem. Rev. 2003, 103, 3899-4032). Although this is certainly a possibility, the polymer dispersities and the lack of strong vibronic features in the PL spectra would preclude the unambiguous assessment of any spectral attenuation as a function of molecular solvent parameters or other definitive spectroscopic characterizations of these states that would be necessary to suggest TICT over other electronic processes
45. Zou, Y.; Gendron, D.; Neagu-Plesu, R.; Leclerc, M. Macromolecules 2009, 42, 6361
46. Pommerehne, J.; Vestweber, H.; Guss, W.; Mahrt, R. F.; Baessler, H.; Porsch, M.; Daub, J. Adv. Mater. 1995, 7, 551
47. Brabec, C. J.; Dyakonov, V.; Scherf, U., Eds.; Organic Photovoltaics; Wiley-VCH: New York, 2008.
48. McCullough, R. D.; Tristram-Nagle, S.; Williams, S. P.; Lowe, R. D.; Jayaraman, M. J. Am. Chem. Soc. 1993, 115, 4910
49. Sonar, P.; Singh, S. P.; Li, Y.; Soh, M. S.; Dodabalapur, A. Adv. Mater. 2010, 22, 5409
50. Li, Y.; Sonar, P.; Singh, S. P.; Zeng, W.; Soh, M. S. J. Mater. Chem. 2011, 21, 10829
51. Chua, L.-L.; Zaumseil, J.; Chang, J.-F.; Ou, E.C.-W.; Ho, P. K.-H.; Sirringhaus, H.; Friend, R. H. Nature 2005, 434, 194