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Supramolecular p−n-Heterojunctions by Co-Self-Organization of Oligo(p-phenylene Vinylene) and Perylene Bisimide Dyes
Abstract
Comparative studies on hydrogen-bonded versus covalently linked donor-acceptor-donor dye arrays obtained from oligo(p-phenylene vinylene)s (OPVs) as donor and bay-substituted perylene bisimides (PERYs) as acceptor dyes are presented. Both systems form well-ordered J-type aggregates in methylcyclohexane, but only hydrogen-bonded arrays afford hierarchically assembled chiral OPV-PERY dye superstructures consisting of left-handed helical pi-pi co-aggregates (CD spectroscopy) of the two dyes that further assemble into right-handed nanometer-scale supercoils in the solid state (AFM study). In the case of hydrogen-bonded arrays, the stability of the aggregates in solution increases with increasing conjugation length of the OPV unit. The well-defined co-aggregated dyes presented here exhibit photoinduced electron transfer on subpicosecond time scale, and thus, these supramolecular entities might serve as valuable nanoscopic functional units.
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Cites
The exciton model in molecular spectroscopy
Kasha, M., Rawls, H. R., & Ashraf El-Bayoumi, M. (1965) · Pure and Applied Chemistry · doi:10.1351/pac196511030371 · Cited by 4,253
Cited by
Yashima, E., Ousaka, N., Taura, D., Shimomura, K., Ikai, T., & Maeda, K. (2016) · Chemical Reviews · doi:10.1021/acs.chemrev.6b00354 · Cited by 2,004
Self-assembled π-stacks of functional dyes in solution: structural and thermodynamic features
Chen, Z., Lohr, A., Saha-Möller, C. R., & Würthner, F. (2009) · Chem. Soc. Rev. · doi:10.1039/b809359h · Cited by 1,051
Self-citationMolecular Materials by Self‐Assembly of Porphyrins, Phthalocyanines, and Perylenes
Elemans, J. A. A. W., van Hameren, R., Nolte, R. J. M., & Rowan, A. E. (2006) · Advanced Materials · doi:10.1002/adma.200502498 · Cited by 668
Hydrogen-bonded Supramolecular π-Functional Materials
González-Rodríguez, D., & Schenning, A. P. H. J. (2011) · Chemistry of Materials · doi:10.1021/cm101817h · Cited by 426
Self-citationRao, K. V., Jayaramulu, K., Maji, T. K., & George, S. J. (2010) · Angewandte Chemie · doi:10.1002/ange.201000527 · Cited by 259
Metadata
- Authors
- 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., Beckers, E. H. A., Meskers, S. C. J., & Janssen, R. A. J.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2004-08-07
- Volume
- 126
- Issue
- 34
- Pages
- 10611-10618
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2102995410
- Cited by
- 411
- References
- 1
- FWCI
- 11.55
- Type
- journal article
- Language
- en
- Open access
- closed
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- 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., Beckers, E. H. A., Meskers, S. C. J., & Janssen, R. A. J. (2004). Supramolecular p−n-Heterojunctions by Co-Self-Organization of Oligo(p-phenylene Vinylene) and Perylene Bisimide Dyes. Journal of the American Chemical Society. https://doi.org/10.1021/ja0475353
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Contains information from the Semantic Scholar Academic Graph Datasets, made available under the ODC Attribution License (ODC-BY 1.0).
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