Diarylindenotetracenes via a selective cross-coupling/C-H functionalization: Electron donors for organic photovoltaic cells

Organic Letters

Volumn 14, Issue 6, 2012, Pages 1390-1393

  Gu, Xingxian ^a   Luhman, Wade A ^a   Yagodkin, Elisey ^a   Holmes, Russell J ^a   Douglas, Christopher J ^a  

^a University of Minnesota   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84858665856     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol300098p     Document Type: Article

References (25)

1. Corriu, R. J. P.; Masse, J. P. J. Chem. Soc., Chem. Commun. 1972, 144a
2. Tamao, K.; Sumitani, K.; Kumada, M. J. Am. Chem. Soc. 1972, 94, 4374
3. Quimby, J. M.; Scott, L. T. Adv. Synth. Catal. 2009, 351, 1009
4. Wegner, H. A.; Scott, L. T.; de Meijere, A. J. Org. Chem. 2003, 68, 883
5. Wang, L.; Shevlin, P. B. Org. Lett. 2000, 2, 3703
6. Yagodkin, E.; Douglas, C. J. Tetrahedron Lett. 2010, 51, 3037
7. Yagodkin, E.; Xia, Y.; Kalihari, V.; Frisbie, C. D.; Douglas, C. J. J. Phys. Chem. C 2009, 113, 16544
8. 1a can be prepared in multigram quantities by a three-step, chromatography-free synthesis from 1,4-naphthalenediol and phthaloyl chloride. See ref 4b and Yagodkin, E.; McGarry, K. A.; Douglas, C. J. Org. Prep. Proc. Int. 2011, 43, 360
9. Taima, T.; Sakai, J.; Yamanari, T.; Saito, K. Jpn. J. Appl. Phys. 2006, 45, L995
10. Perez, M. D.; Borek, C.; Forrest, S. R.; Thompson, M. E. J. Am. Chem. Soc. 2009, 131, 9281
11. Najafov, H.; Lee, B.; Zhou, Q.; Feldman, L. C.; Podzorov, V. Nat. Mater. 2010, 9, 938
12. IR spectrum: Naerland, A. Acta Chem. Scand. 1958, 12, 224
13. UV-vis spectrum: Dufraisse, C.; Amiard, G. Compt. Rend. 1945, 220, 695
14. Melting point and combustion analysis: Dufraisse, C.; Badoche, M. Compt. Rend. 1931, 193, 529
15. Lang, K. F.; Theiling, E. A. Chem. Ber. 1956, 89, 2734
16. Yoo, S.; Domercq, B.; Kippelen, B. Appl. Phys. Lett. 2004, 85, 5427
17. Yoo, S.; Domercq, B.; Kippelen, B. J. Appl. Phys. 2005, 97, 103706
18. Chu, C.; Shao, Y.; Shrotriya, V.; Yang, Y. Appl. Phys. Lett. 2005, 86, 243506
19. Review: Kantchev, E. A. B.; O'Brien, C. J.; Organ, M. M. G. Angew. Chem., Int. Ed. 2007, 46, 2768
20. Use in Kumada-Tamao-Corriu reactions: Organ, M. G.; Abdel-Hadi, M.; Avola, S.; Hadei, N.; Nasielski, J.; O'Brien, C. J.; Valente, C. Chem. - Eur. J. 2007, 13, 150
21. Roman, L. S.; Mammo, W.; Pettersson, L. A. A.; Andersson, M. R.; Inganäs, O. Adv. Mater. 1998, 10, 774
22. Rand, B. P.; Li, J.; Xue, J.; Holmes, R. J.; Thompson, M. E.; Forrest, S. R. Adv. Mater. 2005, 17, 2714
23. Cheyns, D.; Rand, B. P.; Heremans, P. Appl. Phys. Lett. 2010, 97, 033301
24. Pandey, R.; Holmes, R. J. Adv. Mater. 2010, 22, 5301
25. Pettersson, L. A. A.; Roman, L. S.; Inganas, O. J. Appl. Phys 1999, 86, 487