Supramolecular Tessellations by a Rigid Naphthalene Diimide Triangle
Abstract
Tessellation of organic polygons though [π···π] and charge-transfer (CT) interactions offers a unique opportunity to construct supramolecular organic electronic materials with 2D topologies. Our approach to exploring the 3D topology of 2D tessellations of a naphthalene diimide-based molecular triangle (NDI-Δ) reveals that the 2D molecular arrangement is sensitive to the identity of the solvent and solute concentrations. Utilization of nonhalogenated solvents, combined with careful tailoring of the concentrations, results in NDI-Δ self-assembling though [π···π] interactions into 2D honeycomb triangular and hexagonal tiling patterns. Cocrystallization of NDI-Δ with tetrathiafulvalene (TTF) leads systematically to the formation of 2D tessellations as a result of superstructure-directing CT interactions. Different solvents lead to different packing arrangements. Using MeCN, CHCl3, and CH2Cl2, we identified three sets of cocrystals, namely CT-A, CT-B, and CT-C, respectively. Here, solvent modulation plays a critical role in controlling not only the NDI-Δ:TTF stoichiometric ratios and the molecular arrangements in the crystal superstructures, but also prevents the inclusion of TTF guests inside the cavities of NDI-Δ. Confinement of TTF inside the NDI-Δ cavities in the CT-A superstructure enhances the CT character with the observation of a broad absorption band in the NIR region. In the CT-B superstructure, the CHCl3 lattice molecules establishmore »
- Authors:
-
[1];
[1];
[1];
[1];
[1];
[2];
[4]
- Northwestern Univ., Evanston, IL (United States)
- Northwestern Univ., Evanston, IL (United States); Northwestern Univ., Chicago, IL (United States)
- King Abdulaziz City for Science and Technology, Riyadh (Saudi Arabia)
- Northwestern Univ., Evanston, IL (United States); Tianjin Univ. (China); Univ. of New South Wales, Sydney, NSW (Australia)
- Publication Date:
- Research Org.:
- Energy Frontier Research Centers (EFRC) (United States). Center for Bio-Inspired Energy Science (CBES)
- Sponsoring Org.:
- USDOE Office of Science (SC), Basic Energy Sciences (BES)
- OSTI Identifier:
- 1865144
- Grant/Contract Number:
- SC0000989
- Resource Type:
- Accepted Manuscript
- Journal Name:
- Journal of the American Chemical Society
- Additional Journal Information:
- Journal Volume: 141; Journal Issue: 44; Journal ID: ISSN 0002-7863
- Publisher:
- American Chemical Society (ACS)
- Country of Publication:
- United States
- Language:
- English
- Subject:
- 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; Supramolecular chemistry; Molecular interactions; Superstructures; Solvents; Molecules
Citation Formats
Beldjoudi, Yassine, Narayanan, Ashwin, Roy, Indranil, Pearson, Tyler J., Cetin, M. Mustafa, Nguyen, Minh T., Krzyaniak, Matthew D., Alsubaie, Fehaid M., Wasielewski, Michael R., Stupp, Samuel I., and Stoddart, J. Fraser. Supramolecular Tessellations by a Rigid Naphthalene Diimide Triangle. United States: N. p., 2019.
Web. doi:10.1021/jacs.9b08758.
Beldjoudi, Yassine, Narayanan, Ashwin, Roy, Indranil, Pearson, Tyler J., Cetin, M. Mustafa, Nguyen, Minh T., Krzyaniak, Matthew D., Alsubaie, Fehaid M., Wasielewski, Michael R., Stupp, Samuel I., & Stoddart, J. Fraser. Supramolecular Tessellations by a Rigid Naphthalene Diimide Triangle. United States. https://doi.org/10.1021/jacs.9b08758
Beldjoudi, Yassine, Narayanan, Ashwin, Roy, Indranil, Pearson, Tyler J., Cetin, M. Mustafa, Nguyen, Minh T., Krzyaniak, Matthew D., Alsubaie, Fehaid M., Wasielewski, Michael R., Stupp, Samuel I., and Stoddart, J. Fraser. Tue .
"Supramolecular Tessellations by a Rigid Naphthalene Diimide Triangle". United States. https://doi.org/10.1021/jacs.9b08758. https://www.osti.gov/servlets/purl/1865144.
@article{osti_1865144,
title = {Supramolecular Tessellations by a Rigid Naphthalene Diimide Triangle},
author = {Beldjoudi, Yassine and Narayanan, Ashwin and Roy, Indranil and Pearson, Tyler J. and Cetin, M. Mustafa and Nguyen, Minh T. and Krzyaniak, Matthew D. and Alsubaie, Fehaid M. and Wasielewski, Michael R. and Stupp, Samuel I. and Stoddart, J. Fraser},
abstractNote = {Tessellation of organic polygons though [π···π] and charge-transfer (CT) interactions offers a unique opportunity to construct supramolecular organic electronic materials with 2D topologies. Our approach to exploring the 3D topology of 2D tessellations of a naphthalene diimide-based molecular triangle (NDI-Δ) reveals that the 2D molecular arrangement is sensitive to the identity of the solvent and solute concentrations. Utilization of nonhalogenated solvents, combined with careful tailoring of the concentrations, results in NDI-Δ self-assembling though [π···π] interactions into 2D honeycomb triangular and hexagonal tiling patterns. Cocrystallization of NDI-Δ with tetrathiafulvalene (TTF) leads systematically to the formation of 2D tessellations as a result of superstructure-directing CT interactions. Different solvents lead to different packing arrangements. Using MeCN, CHCl3, and CH2Cl2, we identified three sets of cocrystals, namely CT-A, CT-B, and CT-C, respectively. Here, solvent modulation plays a critical role in controlling not only the NDI-Δ:TTF stoichiometric ratios and the molecular arrangements in the crystal superstructures, but also prevents the inclusion of TTF guests inside the cavities of NDI-Δ. Confinement of TTF inside the NDI-Δ cavities in the CT-A superstructure enhances the CT character with the observation of a broad absorption band in the NIR region. In the CT-B superstructure, the CHCl3 lattice molecules establish a set of [Cl···Cl] and [Cl···S] intermolecular interactions, leading to the formation of a hexagonal grid of solvent in which NDI-Δ forms a triangular grid. In the CT-C superstructure, three TTF molecules self-assemble, forming a supramolecular isosceles triangle TTF-Δ, which tiles in a plane alongside the NDI-Δ, producing a 3 + 3 honeycomb tiling pattern of the two different polygons. Solid-state spectroscopic investigations on CT-C revealed the existence of an absorption band at 2500 nm, which on the basis of TDDFT calculations, was attributed to the mixed-valence character between two TTF•+ radical cations and one neutral TTF molecule.},
doi = {10.1021/jacs.9b08758},
journal = {Journal of the American Chemical Society},
number = 44,
volume = 141,
place = {United States},
year = {Tue Sep 17 00:00:00 EDT 2019},
month = {Tue Sep 17 00:00:00 EDT 2019}
}
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