515
Views
9
CrossRef citations to date
0
Altmetric
Original Articles

Navigating the chalcogens: Sulfur substitution for n-type organic materials

&
Pages 664-668 | Received 28 Mar 2019, Accepted 29 Mar 2019, Published online: 13 Apr 2019

References

  • Carrera, E. I.; Seferos, D. S. Semiconducting Polymers Containing Tellurium: Perspectives toward Obtaining High-Performance Materials. Macromolecules 2015, 48, 297–308. DOI:10.1021/ma502307b.
  • Gibson, G. L.; Seferos, D. S. "Heavy-Atom” Donor–Acceptor Conjugated Polymers. Macromol. Chem. Phys. 2014, 215, 811–823. DOI:10.1002/macp.201400042.
  • Pensack, R. D.; Song, Y.; McCormick, T. M.; Jahnke, A. A.; Hollinger, J.; Seferos, D. S.; Scholes, G. D. Evidence for the Rapid Conversion of Primary Photoexcitations to Triplet States in Seleno- and Telluro- Analogues of Poly(3-Hexylthiophene). J. Phys. Chem. B 2014, 118, 2589–2597. DOI:10.1021/jp5013347.
  • Jahnke, A. A.; Djukic, B.; McCormick, T. M.; Domingo, E. B.; Hellmann, C.; Lee, Y.; Seferos, D. S. Poly(3-Alkyltellurophene)s Are Solution-Processable Polyheterocycles. J. Am. Chem. Soc. 2013, 135, 951–954. DOI:10.1021/ja309404j.
  • Hollinger, J.; Jahnke, A. A.; Coombs, N.; Seferos, D. S. Controlling Phase Separation and Optical Properties in Conjugated Polymers through Selenophene-Thiophene Copolymerization. J. Am. Chem. Soc. 2010, 132, 8546–8547. DOI:10.1021/ja103191u.
  • Kynaston, E. L.; Fang, Y.; Manion, J. G.; Obhi, N. K.; Howe, J. Y.; Perepichka, D. F.; Seferos, D. S. Patchy Nanofibers from the Thin Film Self-Assembly of a Conjugated Diblock Copolymer. Angew. Chem. Int. Ed. 2017, 56, 6152–6156. DOI:10.1002/anie.201700134.
  • Gao, D.; Hollinger, J.; Seferos, D. S. Selenophene–Thiophene Block Copolymer Solar Cells with Thermostable Nanostructures. ACS Nano. 2012, 6, 7114–7121. DOI:10.1021/nn3021844.
  • Manion, J. G.; Ye, S.; Proppe, A. H.; Larameé, A. W.; McKeown, G. R.; Kynaston, E. L.; Kelley, S. O.; Sargent, E. H.; Seferos, D. S. Examining Structure–Property–Function Relationships in Thiophene, Selenophene, and Tellurophene Homopolymers. ACS Appl. Energy Mater. 2018, 1, 5033–5042. DOI:10.1021/acsaem.8b01023.
  • Li, P.-F.; Schon, T. B.; Seferos, D. S. Thiophene, Selenophene, and Tellurophene-Based Three-Dimensional Organic Frameworks. Angew. Chem. Int. Ed. 2015, 54, 9361–9366. DOI:10.1002/anie.201503418.
  • Gibson, G. L.; McCormick, T. M.; Seferos, D. S. Atomistic Band Gap Engineering in Donor-Acceptor Polymers. J. Am. Chem. Soc. 2012, 134, 539–547. DOI:10.1021/ja208917m.
  • Guo, X.; Facchetti, A.; Marks, T. J. Imide- and Amide-Functionalized Polymer Semiconductors. Chem. Rev. 2014, 114, 8943–9021. DOI:10.1021/cr500225d.
  • Ie, Y.; Jinnai, S.; Nitani, M.; Aso, Y. Arenedithiocarboxyimide-Containing Extended π-Conjugated Systems with High Electron Affinity. J. Mater. Chem. C. 2013, 1, 5373–5380. DOI:10.1039/c3tc31152j.
  • Yang, T.-F.; Huang, S.-H.; Chiu, Y.-P.; Chen, B.-H.; Shih, Y.-W.; Chang, Y.-C.; Yao, J.-Y.; Lee, Y.-J.; Kuo, M.-Y. Pyromellitic Dithioimides: thionation Improves Air-Stability and Electron Mobility of N-Type Organic Field-Effect Transistors. Chem. Commun. 2015, 51, 13772–13775. DOI:10.1039/c5cc04674b.
  • Tilley, A. J.; Guo, C.; Miltenburg, M. B.; Schon, T. B.; Yan, H.; Li, Y.; Seferos, D. S. Thionation Enhances the Electron Mobility of Perylene Diimide for High Performance n-Channel Organic Field Effect Transistors. Adv. Funct. Mater. 2015, 25, 3321–3329. DOI:10.1002/adfm.201500837.
  • Zhao, Y.; Guo, Y.; Liu, Y. 25th Anniversary Article: recent Advances in n-Type and Ambipolar Organic Field-Effect Transistors. Adv. Mater.2013, 25, 5372–5391. DOI:10.1002/adma.201302315.
  • Tilley, A. J.; Pensack, R. D.; Lee, T. S.; Djukic, B.; Scholes, G. D.; Seferos, D. S. Ultrafast Triplet Formation in Thionated Perylene Diimides. J. Phys. Chem. C 2014, 118, 9996–10004. DOI:10.1021/jp503708d.
  • Kozycz, L. M.; Guo, C.; Manion, J. G.; Tilley, A. J.; Lough, A. J.; Li, Y.; Seferos, D. S. Enhanced Electron Mobility in Crystalline Thionated Naphthalene Diimides. J. Mater. Chem. C 2015, 3, 11505–11515. DOI:10.1039/C5TC02753E.
  • Pahlavanlu, P.; Tilley, A. J.; McAllister, B. T.; Seferos, D. S. Microwave Synthesis of Thionated Naphthalene Diimide-Based Small Molecules and Polymers. J. Org. Chem. 2017, 82, 12337–12345. DOI:10.1021/acs.joc.7b02162.
  • Chen, W.; Zhang, J.; Long, G.; Liu, Y.; Zhang, Q. From Non-Detectable to Decent: replacement of Oxygen with Sulfur in Naphthalene Diimide Boosts Electron Transport in Organic Thin-Film Transistors (OTFT). J. Mater. Chem. C 2015, 3, 8219–8224. DOI:10.1039/C5TC01519G.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.