The New Synthesis of Organic Light-Emitting Material BHBT Monomer by Stille Coupling

Abstract:

Heterocyclic monomer based on 2,1,3-benzothiadiazole bearing solubilizing side chains have been synthesized in high yields over three steps from readily available starting materials. The alkyl side chain in the 4-position of both thiophene rings gives the material mononer a good solubility.

• Periodical: Advanced Materials Research (Volumes 602-604)
• Pages: 1261-1264
• DOI: https://doi.org/10.4028/www.scientific.net/AMR.602-604.1261
• Online since: December 2012
• Authors: Xiao Xiao Zhuang, Xiao Long Lei, Xiao Xia Sun
• Keywords: Donor-Acceptor, Low-Bandgap, Stille Couplling

References

[1] (a) Dennler, G.; Scharber, M. C.; Brabec, C. J. Adv. Mater. 2009, 21, 1323. (b) Park, S. H.; Roy, A.; Beaupre, S.; Cho, S.; Coates, N.;Moon, J. S.; Moses, D.;Leclerc,M.; Lee, K.; Heeger, A. J. Nat. Photonics 2009, 3, 297. (c) Liang, Y.; Feng, D.; Wu, Y.; Tsai, S.-T.; Li, G.; Ray, C.; Yu, L. J. Am. Chem. Soc. 2009, 131, 7792. (d) Hou, J.; Chen, H.-Y.; Zhang, S.; Chen, R. I.; Yang, Y.; Wu, Y.; Li, G. J. Am. Chem. Soc. 2009, 131, 15586. (e) Chen, H.-Y.; Hou, J.; Zhang, S.; Liang, Y.; Yang, G.; Yang, Y.;Yu, L.; Wu, Y.; Li, G. Nat. Photonics 2009, 3, 649.

DOI: 10.1038/nphoton.2009.192

[2] Chen, C.-P.; Chan, S.-H.; Chao, T.-C.; Ting, C.; Ko, B.-T. J. Am. Chem. Soc. 2008, 130, 12828.

[3] Hou, J.; Chen, H.-Y.; Zhang, S.; Li, G.; Yang, Y. J. Am. Chem. Soc. 2008, 130, 16144. (b) Wienk, M. M.; Turbiez, M.; Janssen, R. A. J. Adv. Mater. 2008, 20, 2556. (c) Muhlbacher, D.; Scharber, M.; Morana, M.; Zhu, Z.; Waller, D.; Gaudiana, R.; Brabec, C. Adv. Mater. 2006, 18, 2884. (d) Kim, J. Y.; Lee, K.; Coates, N. E.; Moses, D.; Nguyen, T.-Q.; Dante, M.; Heeger, A. J. Science 2007, 317, 222. (e) Ergang, W.; Li, W.; Linfeng, L.; Chan, L.; Wenliu, Z.; Junbiao, P.; Yong, C. Appl. Phys. Lett. 2008, 92, 033307. (f) Blouin, N.; Michaud, A.; Gendron, D.; Wakim, S.; Blair, E.; Neagu-Plesu, R.; Belletete, M.; Durocher, G.; Tao, Y.; Leclerc, M. J. Am. Chem. Soc. 2008, 130, 732. (g) Svensson, M.; Zhang, F.; Veenstra, S. C.; Verhees, W. J. H.; Hummelen, J. C.; Kroon, J. M.; Inganas, O.; Andersson, M. R. Adv. Mater. 2003, 15, 988. (h) Bundgaard, E.; Krebs, F. C. Macromolecules 2006, 39, 2823.

[4] (a) Thompson, B. C.; Fr_echet, J. M. J. Angew. Chem., Int. Ed. 2008, 47, 58. (b) Gunes, S.; Neugebauer, H.; Sariciftci, N. S. Chem. Rev. 2007, 107, 1324. (c) Li, Y.; Zou, Y. Adv. Mater. 2008, 20, 2952. (d) Dennler, G.; Scharber, M. C.; Brabec, C. J. Adv. Mater. 2009, 21, 1323. (e) Winder, C.; Sariciftci, N. S. J. Mater. Chem. 2004, 14, 1077. (f) Bundgaard, E.; Krebs, F. C. Sol. Energy Mater. Sol. Cells 2007, 91, 954. (g) Kroon, R.; Lenes, M.; Hummelen, J. C.; Blom, P. W. M.; de Boer, B. Polym. Rev. 2008, 48, 531. (h) Helgesen, M.; Sondergaard, R.; Krebs, F. C. J. Mater. Chem. 2010, 20, 36. (i) Chen, J.; Cao, Y. Acc. Chem. Res. 2009, 42, 1709.

DOI: 10.1039/b913168j

[5] (a) Sonmez, G.; Shen, C. K. F.; Rubin, Y.; Wudl, F. Angew. Chem., Int. Ed. 2004, 43, 1498. (b) Sonmez, G. Chem. Commun. 2005, 5251.

[6] Kang, S. K.; Lee, H. W.; Jang, S. B.; Kim, T. H.; Kim, J. S. Synth. Commun. 1996, 26, 4311.