The DOI matches its Crossref record; 22 of the 22 references it cites were found in a registry or an index.
Chlorination: A General Route toward Electron Transport in Organic Semiconductors
Abstract
We show that adding chlorine atoms to conjugated cores is a general, effective route toward the design of n-type air-stable organic semiconductors. We find this to be true for acenes, phthalocyanines, and perylene tetracarboxylic diimide (PDI)-based molecules. This general finding opens new avenues in the design and synthesis of organic semiconductors. We compared a series of fluoro- and chloro-functionalized acenes, phthalocyanines, and PDI-based molecules. The acenes synthesized showed high and balanced ambipolar transport in the top-contact organic field effect transistor (OFET) geometry. The electron-withdrawing halogen groups lowered the LUMO and the charge injection barrier for electrons, such that electron and hole transport occurred simultaneously. If the chlorine added does not distort the planarity of the conjugated core, we found that the chloro-functionalized molecules tend to have a slightly smaller HOMO-LUMO gap and a lower LUMO level than the fluoro-containing molecules, both from calculations and cyclic voltammetry measurements in solution. This is most likely due to the fact that Cl contains empty 3d orbitals that can accept pi-electrons from the conjugated core, while F does not have energetically accessible empty orbitals for such delocalization.
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Citations
Cites
Conjugated Polymer-Based Organic Solar Cells
Günes, S., Neugebauer, H., & Sariciftci, N. S. (2007) · Chemical Reviews · doi:10.1021/cr050149z · Cited by 6,279
Electroluminescence in conjugated polymers
Friend, R. H., Gymer, R. W., Holmes, A. B., Burroughes, J. H., Marks, R. N., Taliani, C., Bradley, D. D. C., Santos, D. A. D., Brédas, J. L., Lögdlund, M., et al. (1999) · Nature · doi:10.1038/16393 · Cited by 5,977
Charge Transport in Organic Semiconductors
Coropceanu, V., Cornil, J., da Silva Filho, D. A., Olivier, Y., Silbey, R., & Brédas, J.-L. (2007) · Chemical Reviews · doi:10.1021/cr050140x · Cited by 4,607
Device Physics of Polymer:Fullerene Bulk Heterojunction Solar Cells
Blom, P. W. M., Mihailetchi, V. D., Koster, L. J. A., & Markov, D. E. (2007) · Advanced Materials · doi:10.1002/adma.200601093 · Cited by 2,299
General observation of n-type field-effect behaviour in organic semiconductors
Chua, L.-L., Zaumseil, J., Chang, J.-F., Ou, E. C.-W., Ho, P. K.-H., Sirringhaus, H., & Friend, R. H. (2005) · Nature · doi:10.1038/nature03376 · Cited by 2,264
Electron and Ambipolar Transport in Organic Field-Effect Transistors
Zaumseil, J., & Sirringhaus, H. (2007) · Chemical Reviews · doi:10.1021/cr0501543 · Cited by 2,197
Electronegativity values from thermochemical data
Allred, A. L. (1961) · Journal of Inorganic and Nuclear Chemistry · doi:10.1016/0022-1902(61)80142-5 · Cited by 2,066
Organic Semiconducting Oligomers for Use in Thin Film Transistors
Murphy, A. R., & Fréchet, J. M. J. (2007) · Chemical Reviews · doi:10.1021/cr0501386 · Cited by 1,863
Charge Carrier Transporting Molecular Materials and Their Applications in Devices
Shirota, Y., & Kageyama, H. (2007) · Chemical Reviews · doi:10.1021/cr050143+ · Cited by 1,756
Highly Efficient Organic Devices Based on Electrically Doped Transport Layers
Walzer, K., Maennig, B., Pfeiffer, M., & Leo, K. (2007) · Chemical Reviews · doi:10.1021/cr050156n · Cited by 1,560
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Lin, Y., Li, Y., & Zhan, X. (2012) · Chemical Society Reviews · doi:10.1039/c2cs15313k · Cited by 1,751
Integrated Materials Design of Organic Semiconductors for Field-Effect Transistors
Mei, J., Diao, Y., Appleton, A. L., Fang, L., & Bao, Z. (2013) · Journal of the American Chemical Society · doi:10.1021/ja400881n · Cited by 1,443
Self-citationDelgado, M. C. R., Kim, E.-G., Filho, D. A. D. S., & Bredas, J.-L. (2010) · Journal of the American Chemical Society · doi:10.1021/ja908173x · Cited by 356
Control of π–π Stacking via Crystal Engineering in Organic Conjugated Small Molecule Crystals
Yao, Z.-F., Wang, J.-Y., & Pei, J. (2018) · Crystal Growth & Design · doi:10.1021/acs.cgd.7b01385 · Cited by 328
Sutton, C., Risko, C., & Brédas, J.-L. (2016) · Chemistry of Materials · doi:10.1021/acs.chemmater.5b03266 · Cited by 265
Metadata
- Authors
- Tang, M. L., Oh, J. H., Reichardt, A. D., & Bao, Z.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2009-02-25
- Volume
- 131
- Issue
- 10
- Pages
- 3733-3740
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2026525600
- Cited by
- 370
- References
- 22
- FWCI
- 22.44
- Type
- journal article
- Language
- en
- Open access
- closed
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