Ambipolar organic semiconductors and NIR chromophores

Among others, ambipolar organic semiconductors are emerging as interesting materials owing to their flexibility and their use in a variety of device architectures in different areas of organic electronics

Quinoidal oligothiophenes have been shown to be promising materials for their proven amphoteric properties. The longer members in the series show near-infrared (NIR) absorption features, driven by the reduction of their HOMO-LUMO energy gap, that make them of potential use in the field of organic photodetectors. NIR absorptions are desirable, for instance, to increase the efficiency of solar cells.

Another signature of the energy gap decrease occurring in chromophores with small HOMO-LUMO gaps is their increasing biradicaloid character.

Biradicaloids are suitable systems for singlet fission, a process that  has recently received renewed interest because it enables the generation of a pair of charge separated triplet states and provides a strategy to generate two electron-hole pairs from a single photon, thereby increasing the efficiency of solar cells.

References

  • S. Di Motta, F. Negri, D. Fazzi, C. Castiglioni, E. V. Canesi, “Biradicaloid and Polyenic Character of Quinoidal Oligothiophenes Reve aled by the Presence of a Low-Lying Double-Exciton State”, J. Phys. Chem. Lett.,  1, (2010) 3334-3339.
  • D. Fazzi, E. V. Canesi, F. Negri, C. Bertarelli, C. Castiglioni “Biradicaloid Character of Thiophene Based Heterophenoquinones: the Role of Electron-Phonon Coupling”, ChemPhysChem., 11, (2010), 3685-3695.
  • W. Yue , J. Gao , Y. Li , W. Jiang, S. Di Motta, F. Negri, Z. Wang, "One-pot Synthesis of Stable NIR tetracene Diimides via Double cross-Coupling",  J. Am. Chem. Soc,  133, (2011) 18054-18057.
  • W. Yue, A. Lv, J. Gao, W. Jiang, L. Hao, C. Li, Y. Li, L. E. Polander, S. Barlow, W. Hu, S. Di Motta, F. Negri, S. R. Marder, Z. Wang, "Hybrid Rylene Arrays via Combination of Stille Coupling and C-H Transformation as High Performance Electron Transport Materials", J. Am. Chem. Soc, 134, (2012), 5770-5773. http://dx.doi.org/10.1021/ja301184r
  • G. Liu, C. Xiao, F. Negri, Y. Li, Z. Wang, "Dodecatwistarene Imides with Zigzag‐Twisted Conformation for Organic Electronics", Angew. Chem. Int. Ed., 59, (2020), 2008-2012, DOI: 10.1002/anie.201912356