DArP synthesis scheme: brominated 3-hexylthiophene monomer converted by direct arylation polymerization to regioregular P3HT [P2513]

Regioregular Organic Semiconducting Polymer as Donor and Hole Transport Material

Regioregular P3HT (P2513) is an organic semiconducting polymer with very high regioregularity. It is prepared by direct arylation polymerization (DArP)¹) and offers RR >99.0%, Mn 27,000–45,000, and electronic-grade purity with Pd <100 ppm. Its high solubility allows solution processing and excellent film formation. In organic photovoltaics (OPV), P3HT serves as a donor that forms a bulk heterojunction (BHJ) with a highly soluble acceptor³),⁴). In perovskite solar cells (PSC), it is used as a hole transport material (HTM)⁵), while in organic field-effect transistors (OFET) it functions as a p-type semiconductor⁶). Compared with the Rieke and GRIM methods, DArP-prepared P3HT reaches RR 99.5%, Tm 237 °C, and µmax 0.19 cm²/V·s, whereas the Rieke and GRIM methods give 0.02 and 0.11 cm²/V·s, respectively¹),²).

DArP synthesis scheme: brominated 3-hexylthiophene monomer converted by direct arylation polymerization to regioregular P3HT [P2513]
Source: TCI brochure FF065
OPV device architecture (cathode, donor P3HT and acceptor bulk heterojunction, anode, substrate)
Source: TCI brochure FF065

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References

  1. Palladium-Catalyzed Dehydrohalogenative Polycondensation of 2-Bromo-3-hexylthiophene: An Efficient Approach to Head-to-Tail Poly(3-hexylthiophene). Q. Wang, R. Takita, Y. Kikuzaki, F. Ozawa, J. Am. Chem. Soc. 2010, 132, 11420. doi:10.1021/ja105767z
  2. J.-R. Pouliot, M. Leclerc, et al., Macromol. Chem. Phys. 2016, 217, 1493. doi:10.1002/macp.201600050
  3. E. L. Lim, M. H. H. Jumali, et al., Org. Electron. 2016, 36, 12. (OPV, ref. 1a) doi:10.1016/j.orgel.2016.05.029
  4. A. Marrocchi, D. Lanari, A. Facchetti, L. Vaccaro, Energy Environ. Sci. 2012, 5, 8457. (OPV, ref. 1b) doi:10.1039/C2EE22129B
  5. L. Calió, S. Kazim, M. Grätzel, S. Ahmad, Angew. Chem. Int. Ed. 2016, 55, 14522. (PSC, ref. 2) doi:10.1002/anie.201601757
  6. H. Sirringhaus, Adv. Mater. 2014, 26, 1319. (OFET, ref. 3) doi:10.1002/adma.201304346

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