Charge Transfer Dynamics in Supramolecular Tessellations Composed of Aromatic Donors and Chiral Tris(naphthalenediimide) Triangular Acceptors

Malik L. Williams; Jonathan R. Palmer; Ryan M. Young; Michael R. Wasielewski

doi:10.1021/jacs.4c13800

Charge Transfer Dynamics in Supramolecular Tessellations Composed of Aromatic Donors and Chiral Tris(naphthalenediimide) Triangular Acceptors

Malik L. Williams, Jonathan R. Palmer, Ryan M. Young, Michael R. Wasielewski^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

Abstract

Understanding charge transfer (CT) dynamics in donor-acceptor (D-A) cocrystals is important for the development of efficient organic photovoltaic and electronic materials. This study explores the photogenerated CT states of supramolecular tessellations formed by cocrystallizing a chiral tris(naphthalenediimide) triangular prism (−)-NDI-Δ with pyrene, perylene, and peri-xanthenoxanthene electron donors. By manipulating crystallization conditions, one-dimensional (1D) and two-dimensional (2D) cocrystals with distinct structural motifs and morphologies are achieved. Femtosecond and nanosecond transient absorption microscopies and time-resolved electron paramagnetic resonance spectroscopy were employed to elucidate the CT state dynamics. Our findings reveal that the CT state lifetimes are lengthened in the 2D cocrystals relative to the 1D cocrystals, which is attributable to the symmetry and molecular packing differences between them that modulate the CT interactions. This work highlights the potential of using preorganized covalent multisite charge carriers as donors or acceptors in cocrystals as a strategy for engineering structures for advanced multifunctional materials with tunable CT properties.

Original language	English (US)
Pages (from-to)	34130-34140
Number of pages	11
Journal	Journal of the American Chemical Society
Volume	146
Issue number	49
DOIs	https://doi.org/10.1021/jacs.4c13800
State	Published - Dec 11 2024

Funding

This work was supported by the US Department of Energy, Office of Science, Office of Basic Energy Sciences, under award no. DE-FG02-99ER14999 (M.R.W.). This work made use of the IMSERC MS and NMR facility at Northwestern University, which has received support from the Soft and Hybrid Nanotechnology Experimental (SHyNE) Resource (NSF ECCS-2025633), the State of Illinois, the International Institute for Nanotechnology (IIN) and Northwestern University. J. R. P. was supported by the NSF Graduate Research Fellowship Program under grant no. DGE-2234667. Any opinions, findings, and conclusions or recommendations expressed in this material are those of the author(s) and do not necessarily reflect the views of the National Science Foundation.

ASJC Scopus subject areas

Catalysis
General Chemistry
Biochemistry
Colloid and Surface Chemistry

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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title = "Charge Transfer Dynamics in Supramolecular Tessellations Composed of Aromatic Donors and Chiral Tris(naphthalenediimide) Triangular Acceptors",

abstract = "Understanding charge transfer (CT) dynamics in donor-acceptor (D-A) cocrystals is important for the development of efficient organic photovoltaic and electronic materials. This study explores the photogenerated CT states of supramolecular tessellations formed by cocrystallizing a chiral tris(naphthalenediimide) triangular prism (−)-NDI-Δ with pyrene, perylene, and peri-xanthenoxanthene electron donors. By manipulating crystallization conditions, one-dimensional (1D) and two-dimensional (2D) cocrystals with distinct structural motifs and morphologies are achieved. Femtosecond and nanosecond transient absorption microscopies and time-resolved electron paramagnetic resonance spectroscopy were employed to elucidate the CT state dynamics. Our findings reveal that the CT state lifetimes are lengthened in the 2D cocrystals relative to the 1D cocrystals, which is attributable to the symmetry and molecular packing differences between them that modulate the CT interactions. This work highlights the potential of using preorganized covalent multisite charge carriers as donors or acceptors in cocrystals as a strategy for engineering structures for advanced multifunctional materials with tunable CT properties.",

author = "Williams, {Malik L.} and Palmer, {Jonathan R.} and Young, {Ryan M.} and Wasielewski, {Michael R.}",

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N2 - Understanding charge transfer (CT) dynamics in donor-acceptor (D-A) cocrystals is important for the development of efficient organic photovoltaic and electronic materials. This study explores the photogenerated CT states of supramolecular tessellations formed by cocrystallizing a chiral tris(naphthalenediimide) triangular prism (−)-NDI-Δ with pyrene, perylene, and peri-xanthenoxanthene electron donors. By manipulating crystallization conditions, one-dimensional (1D) and two-dimensional (2D) cocrystals with distinct structural motifs and morphologies are achieved. Femtosecond and nanosecond transient absorption microscopies and time-resolved electron paramagnetic resonance spectroscopy were employed to elucidate the CT state dynamics. Our findings reveal that the CT state lifetimes are lengthened in the 2D cocrystals relative to the 1D cocrystals, which is attributable to the symmetry and molecular packing differences between them that modulate the CT interactions. This work highlights the potential of using preorganized covalent multisite charge carriers as donors or acceptors in cocrystals as a strategy for engineering structures for advanced multifunctional materials with tunable CT properties.

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Charge Transfer Dynamics in Supramolecular Tessellations Composed of Aromatic Donors and Chiral Tris(naphthalenediimide) Triangular Acceptors

Abstract

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UN SDGs

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