Document Type
Article
Publication Date
2025
DOI
10.1021/jacs.5c06649
Publication Title
Journal of the American Chemical Society
Volume
147
Issue
45
Pages
41261-41271
Abstract
Organic electronics, featuring π-conjugated small molecules and polymers, have gained significant attention for their potential in flexible, lightweight devices. However, characterization of the ordered, π-stacking domains within these materials using microscopy or X-ray diffraction (XRD) is challenging with complex systems or when crystallography is impractical. This study applied 1D ¹³C multiple cross-polarization magic angle spinning (multiCP/MAS) and 2D ¹H-¹³C heteronuclear correlation (HetCor) solid-state nuclear magnetic resonance (ssNMR) to systematically characterize π-stacking motifs in a series of N,N'-dialkyl naphthalene diimides (NDIs). These techniques were shown to distinguish between the electronic environments attributed to different π-stacking motifs adopted in these NDIs, such that distinct packing types could be identified by their ssNMR "fingerprints" without requiring growth of XRD-quality crystals. Density functional theory (DFT) supported the experimental data by linking observed motifs with calculated chemical shifts and electronic effects due to stack-bonding interactions. These results lay the foundation for systematic ssNMR characterization of π-stacking domains in diverse organic materials, particularly in complex or blended systems where crystallography is challenging.
Rights
© 2025 The Authors.
This article is licensed under a Creative Commons Attribution 4.0 International (CC-BY-4.0).
Original Publication Citation
Mejia, J. E., Butler-Au, H. E., Thompson, N. E., Goldman, K. D., Zengel, E. R., Pike, R. D., Mao, J., & Bayse, C. A. (2025). Identification of π-stacking motifs in naphthalene diimides via solid-state NMR. Journal of the American Chemical Society, 147(45), 41261-41271. https://doi.org/10.1021/jacs.5c06649
ORCID
0000-0003-0604-7451 (Mao), 0000-0002-3490-576X (Bayse)
Repository Citation
Mejia, Jennifer E.; Butler-Au, Hannah E.; Thompson, Nalaya E.; Goodman, Karcher D.; Zengel, Elizabeth R.; Pike, Robert D.; Mao, Jingdong; and Bayse, Craig A., "Identification of π-Stacking Motifs in Naphthalene Diimides via Solid-State NMR" (2025). Chemistry & Biochemistry Faculty Publications. 379.
https://digitalcommons.odu.edu/chemistry_fac_pubs/379
Supporting Information