Photoannealing of Merocyanine Aggregates
Abstract
In this study we elucidate the fundamental difference between aggregate formation of donor–π–acceptor merocyanines in their electronic ground and excited states. While increasing the π-bridge size favors formation of π-stacked aggregates in the dark, irradiation with visible light causes reorientation of the dyes to form prototype H-aggregates with compensating dipole moments. This photoannealing changes the supramolecular structure and its UV–vis spectroscopic properties dramatically, thus being of importance for the function of active layers composed of these dyes. Aggregates of the ground state dyes are bound cooperatively through ππ-London dispersion interactions and hydrogen bonds between the polar α-cyano-carboxylic acid groups. However, charge transfer upon photoexcitation leads to repulsion of the polar acid groups. Electronic excitation of the dyes approximately doubles the ground state dipole moment, thus driving molecular reorientation into prototype H-aggregate structures. We show that this photoinduced supramolecular rearrangement can disrupt the large polymeric aggregates formed in the dark. The photoinduced supramolecular structural changes reported in this work will influence the performance of optoelectronic devices composed of these structures and must be controlled to avoid morphological decomposition of active layers upon operation.
- Authors:
-
- Friedrich Schiller Univ. Jena, Jena (Germany); Leibniz Institute of Photonic Technology Jena (IPHT), Jena (Germany)
- Friedrich Schiller Univ. Jena, Jena (Germany)
- Leibniz Institute of Photonic Technology Jena (IPHT), Jena (Germany)
- SLAC National Accelerator Lab., Menlo Park, CA (United States); Friedrich Schiller Univ. Jena, Jena (Germany)
- Friedrich Schiller Univ. Jena, Jena (Germany); Leibniz Institute of Photonic Technology Jena (IPHT), Jena (Germany); sciclus GmbH & Co. KG, Jena (Germany)
- Publication Date:
- Research Org.:
- SLAC National Accelerator Lab., Menlo Park, CA (United States)
- Sponsoring Org.:
- USDOE
- OSTI Identifier:
- 1493575
- Grant/Contract Number:
- AC02-76SF00515; 03EK3507; PR 1415/2-1
- Resource Type:
- Accepted Manuscript
- Journal Name:
- Journal of Physical Chemistry. A, Molecules, Spectroscopy, Kinetics, Environment, and General Theory
- Additional Journal Information:
- Journal Volume: 122; Journal Issue: 51; Journal ID: ISSN 1089-5639
- Publisher:
- American Chemical Society
- Country of Publication:
- United States
- Language:
- English
- Subject:
- 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
Citation Formats
Herrmann-Westendorf, Felix, Sachse, Torsten, Schulz, Martin, Kaufmann, Martin, Sivakov, Vladimir, Beckert, Rainer, Martínez, Todd, Dietzek, Benjamin, and Presselt, Martin. Photoannealing of Merocyanine Aggregates. United States: N. p., 2018.
Web. doi:10.1021/acs.jpca.8b09048.
Herrmann-Westendorf, Felix, Sachse, Torsten, Schulz, Martin, Kaufmann, Martin, Sivakov, Vladimir, Beckert, Rainer, Martínez, Todd, Dietzek, Benjamin, & Presselt, Martin. Photoannealing of Merocyanine Aggregates. United States. https://doi.org/10.1021/acs.jpca.8b09048
Herrmann-Westendorf, Felix, Sachse, Torsten, Schulz, Martin, Kaufmann, Martin, Sivakov, Vladimir, Beckert, Rainer, Martínez, Todd, Dietzek, Benjamin, and Presselt, Martin. Fri .
"Photoannealing of Merocyanine Aggregates". United States. https://doi.org/10.1021/acs.jpca.8b09048. https://www.osti.gov/servlets/purl/1493575.
@article{osti_1493575,
title = {Photoannealing of Merocyanine Aggregates},
author = {Herrmann-Westendorf, Felix and Sachse, Torsten and Schulz, Martin and Kaufmann, Martin and Sivakov, Vladimir and Beckert, Rainer and Martínez, Todd and Dietzek, Benjamin and Presselt, Martin},
abstractNote = {In this study we elucidate the fundamental difference between aggregate formation of donor–π–acceptor merocyanines in their electronic ground and excited states. While increasing the π-bridge size favors formation of π-stacked aggregates in the dark, irradiation with visible light causes reorientation of the dyes to form prototype H-aggregates with compensating dipole moments. This photoannealing changes the supramolecular structure and its UV–vis spectroscopic properties dramatically, thus being of importance for the function of active layers composed of these dyes. Aggregates of the ground state dyes are bound cooperatively through ππ-London dispersion interactions and hydrogen bonds between the polar α-cyano-carboxylic acid groups. However, charge transfer upon photoexcitation leads to repulsion of the polar acid groups. Electronic excitation of the dyes approximately doubles the ground state dipole moment, thus driving molecular reorientation into prototype H-aggregate structures. We show that this photoinduced supramolecular rearrangement can disrupt the large polymeric aggregates formed in the dark. The photoinduced supramolecular structural changes reported in this work will influence the performance of optoelectronic devices composed of these structures and must be controlled to avoid morphological decomposition of active layers upon operation.},
doi = {10.1021/acs.jpca.8b09048},
journal = {Journal of Physical Chemistry. A, Molecules, Spectroscopy, Kinetics, Environment, and General Theory},
number = 51,
volume = 122,
place = {United States},
year = {Fri Nov 30 00:00:00 EST 2018},
month = {Fri Nov 30 00:00:00 EST 2018}
}
Web of Science
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