The DOI matches its Crossref record; 40 of the 40 references it cites were found in a registry or an index.
Tuning the Charge-Transport Parameters of Perylene Diimide Single Crystals via End and/or Core Functionalization: A Density Functional Theory Investigation
Abstract
Perylene tetracarboxylic diimide (PTCDI) derivatives stand out as one of the most investigated families of air-stable n-type organic semiconductors for organic thin-film transistors. Here, we use density functional theory to illustrate how it is possible to control the charge-transport parameters of PTCDIs as a function of the type, number, and positions of the substituents. Specifically, two strategies of functionalization related to core and end substitutions are investigated. While end-substituted PTCDIs present the same functional molecular backbone, their molecular packing in the crystal significantly varies; as a consequence, this series of derivatives constitutes an ideal test bed to evaluate the models that describe charge-transport in organic semiconductors. Our results indicate that large bandwidths along with small effective masses can be obtained with the insertion of appropriate substituents on the nitrogens, in particular halogenated aromatic groups.
Overview
The claims and statistics of this paper haven’t been checked yet.
Run the check — free, no account needed. It reads the open-access text and checks the sources it cites.
Integrity signals
Registry
Cites
Statistics
Verification
Claims the paper makes
The claims and statistics of this paper haven’t been checked yet.
Run the check — free, no account needed. It reads the open-access text and checks the sources it cites.
Self-check
Percentages, sums and reported differences re-computed from the paper’s own numbers.
The self-check needs the paper’s full text.
Citations
Cites
Density-functional thermochemistry. III. The role of exact exchange
Becke, A. D. (1993) · The Journal of Chemical Physics · doi:10.1063/1.464913 · Cited by 103,767
Lee, C., Yang, W., & Parr, R. G. (1988) · Physical Review B · doi:10.1103/physrevb.37.785 · Cited by 100,874
Special points for Brillouin-zone integrations
Monkhorst, H. J., & Pack, J. D. (1976) · Physical Review B · doi:10.1103/physrevb.13.5188 · Cited by 71,721
Soft self-consistent pseudopotentials in a generalized eigenvalue formalism
Vanderbilt, D. (1990) · Physical Review B · doi:10.1103/physrevb.41.7892 · Cited by 23,185
Hehre, W. J., Ditchfield, R., & Pople, J. A. (1972) · The Journal of Chemical Physics · doi:10.1063/1.1677527 · Cited by 15,855
Francl, M. M., Pietro, W. J., Hehre, W. J., Binkley, J. S., Gordon, M. S., DeFrees, D. J., & Pople, J. A. (1982) · The Journal of Chemical Physics · doi:10.1063/1.444267 · Cited by 8,187
Über die Zuordnung von Wellenfunktionen und Eigenwerten zu den Einzelnen Elektronen Eines Atoms
Koopmans, T. (1934) · Physica · doi:10.1016/s0031-8914(34)90011-2 · Cited by 7,754
Clark, T., Chandrasekhar, J., Spitznagel, G. W., & Schleyer, P. V. R. (1983) · Journal of Computational Chemistry · doi:10.1002/jcc.540040303 · Cited by 7,224
Two-layer organic photovoltaic cell
Tang, C. W. (1986) · Applied Physics Letters · doi:10.1063/1.96937 · Cited by 5,002
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
Electron transfer reactions in chemistry. Theory and experiment
Marcus, R. A. (1993) · Reviews of Modern Physics · doi:10.1103/revmodphys.65.599 · Cited by 3,667
Brédas, J.-L., Beljonne, D., Coropceanu, V., & Cornil, J. (2004) · Chemical Reviews · doi:10.1021/cr040084k · Cited by 2,878
Electronic Processes in Organic Crystals and Polymers
Pope, M., & Swenberg, C. E. (1999) · doi:10.1093/oso/9780195129632.001.0001 · Cited by 2,562
Self-Organized Discotic Liquid Crystals for High-Efficiency Organic Photovoltaics
Schmidt-Mende, L., Fechtenkötter, A., Müllen, K., Moons, E., Friend, R. H., & MacKenzie, J. D. (2001) · Science · doi:10.1126/science.293.5532.1119 · Cited by 2,378
Perylene bisimide dyes as versatile building blocks for functional supramolecular architectures
Würthner, F. (2004) · Chem. Commun. · doi:10.1039/b401630k · Cited by 2,254
Brédas, J. L., Calbert, J. P., da Silva Filho, D. A., & Cornil, J. (2002) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.092143399 · Cited by 1,276
Zhan, X., Tan, Z., Domercq, B., An, Z., Zhang, X., Barlow, S., Li, Y., Zhu, D., Kippelen, B., & Marder, S. R. (2007) · Journal of the American Chemical Society · doi:10.1021/ja071760d · Cited by 1,172
Jones, B. A., Facchetti, A., Wasielewski, M. R., & Marks, T. J. (2007) · Journal of the American Chemical Society · doi:10.1021/ja075242e · Cited by 1,056
Jones, B. A., Ahrens, M. J., Yoon, M., Facchetti, A., Marks, T. J., & Wasielewski, M. R. (2004) · Angewandte Chemie International Edition · doi:10.1002/anie.200461324 · Cited by 871
Effect of Electronic Polarization on Charge-Transport Parameters in Molecular Organic Semiconductors
Valeev, E. F., Coropceanu, V., da Silva Filho, D. A., Salman, S., & Brédas, J.-L. (2006) · Journal of the American Chemical Society · doi:10.1021/ja061827h · Cited by 862
Reimers, J. R. (2001) · The Journal of Chemical Physics · doi:10.1063/1.1412875 · Cited by 687
Spano, F. C. (2005) · The Journal of Chemical Physics · doi:10.1063/1.1914768 · Cited by 640
Briseño, A. L., Mannsfeld, S. C. B., Reese, C., et al. (2007) · Nano Letters · doi:10.1021/nl071495u · Cited by 430
Senthilkumar, K., Grozema, F. C., Bickelhaupt, F. M., & Siebbeles, L. D. A. (2003) · The Journal of Chemical Physics · doi:10.1063/1.1615476 · Cited by 430
Würthner, F., Chen, Z., Hoeben, F. J. M., Osswald, P., You, C.-C., Jonkheijm, P., Herrikhuyzen, J. V., Schenning, A. P. H. J., van der Schoot, P. P. A. M., Meijer, E. W., et al. (2004) · Journal of the American Chemical Society · doi:10.1021/ja0475353 · Cited by 411
Chlorination: A General Route toward Electron Transport in Organic Semiconductors
Tang, M. L., Oh, J. H., Reichardt, A. D., & Bao, Z. (2009) · Journal of the American Chemical Society · doi:10.1021/ja809045s · Cited by 370
Kazmaier, P. M., & Hoffmann, R. (1994) · Journal of the American Chemical Society · doi:10.1021/ja00100a038 · Cited by 366
Preparation and Characterization of Regioisomerically Pure 1,7-Disubstituted Perylene Bisimide Dyes
Würthner, F., Stepanenko, V., Chen, Z., Saha-Möller, C. R., Kocher, N., & Stalke, D. (2004) · The Journal of Organic Chemistry · doi:10.1021/jo048880d · Cited by 345
Polarization Energies in Oligoacene Semiconductor Crystals
Norton, J. E., & Brédas, J.-L. (2008) · Journal of the American Chemical Society · doi:10.1021/ja8017797 · Cited by 344
Nitrogen-Rich Oligoacenes: Candidates for n-Channel Organic Semiconductors
Winkler, M., & Houk, K. N. (2007) · Journal of the American Chemical Society · doi:10.1021/ja067087u · Cited by 340
Seeger, K. (2004) · Advanced Texts in Physics · doi:10.1007/978-3-662-09855-4 · Cited by 335
Klebe, G., Graser, F., Hädicke, E., & Berndt, J. (1989) · Acta Crystallographica Section B Structural Science · doi:10.1107/s0108768188010407 · Cited by 305
Shin, W. S., Jeong, H.-H., Kim, M.-K., Jin, S.-H., Kim, M.-R., Lee, J.-K., Lee, J. W., & Gal, Y.-S. (2006) · J. Mater. Chem. · doi:10.1039/b512983d · Cited by 287
Schmidt, R., Ling, M. M., Oh, J. H., Winkler, M., Könemann, M., Bao, Z., & Würthner, F. (2007) · Advanced Materials · doi:10.1002/adma.200701478 · Cited by 240
Chen, H. Z., Ling, M. M., Mo, X., Shi, M. M., Wang, M., & Bao, Z. (2007) · Chemistry of Materials · doi:10.1021/cm062352w · Cited by 227
Effects of Arylene Diimide Thin Film Growth Conditions on n‐Channel OFET Performance
Jones, B. A., Facchetti, A., Wasielewski, M. R., & Marks, T. J. (2008) · Advanced Functional Materials · doi:10.1002/adfm.200701045 · Cited by 213
A multimode analysis of the gas-phase photoelectron spectra in oligoacenes
Malagoli, M., Coropceanu, V., da Silva Filho, D. A., & Brédas, J. L. (2004) · The Journal of Chemical Physics · doi:10.1063/1.1687675 · Cited by 174
Structures of eleven perylene-3,4:9,10-bis(dicarboximide) pigments
Hädicke, E., & Graser, F. (1986) · Acta Crystallographica Section C Crystal Structure Communications · doi:10.1107/s0108270186096828 · Cited by 156
Anisotropy of the mobility of pentacene from frustration
de Wijs, G. A., Mattheus, C. C., de Groot, R. A., & Palstra, T. T. M. (2003) · Synthetic Metals · doi:10.1016/s0379-6779(03)00020-1 · Cited by 133
Zhao, H.-M., Pfister, J., Settels, V., Renz, M., Kaupp, M., Dehm, V., Würthner, F., Fink, R. F., & Engels, B. (2009) · Journal of the American Chemical Society · doi:10.1021/ja902512e · Cited by 113
Metadata
- Authors
- Delgado, M. C. R., Kim, E.-G., Filho, D. A. D. S., & Bredas, J.-L.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2010-02-18
- Volume
- 132
- Issue
- 10
- Pages
- 3375-3387
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2000456123
- Cited by
- 356
- References
- 40
- FWCI
- 20.93
- Type
- journal article
- Language
- en
- Open access
- closed
About these checks
Registry, retraction, Cites and statistics results are computed, not judged, with one exception: a printed reference that no index lists is read once by a model before it counts as a citation error. Claims are extracted by a model and kept only when their quote appears verbatim in the text; each cited source is then checked, with a model’s help, for whether it says what the claim relies on. Those verdicts can be wrong — read the claim’s quote and the cited source before relying on one.
Statistics and arithmetic are recomputed, not judged.
Confidence bands are shown only for fields calibrated on our annotated test set. None is calibrated yet, so no band is shown.
What counts as a claim ›How we measure confidence ›How we check this ›
Are you an author, or do you see a problem with this page? Request a review
Data sources
Bibliographic data: Semantic Scholar, OpenAlex, Crossref.
Contains information from the Semantic Scholar Academic Graph Datasets, made available under the ODC Attribution License (ODC-BY 1.0).
Semantic Scholar’s data is described in: Kinney, R., et al. (2023). The Semantic Scholar Open Data Platform. arXiv:2301.10140.
