Two Blatter Radicals Face-to-Face: A Constrained Diradical Architecture
Cofacial arrangement of two Blatter radicals enforced by the <i>peri</i>-naphthalene scaffold represents a new approach to stable diradicals with strong through-space interactions. Two stereoisomers of the naphthalene-diradicals, <i>anti</i> and <i>syn</i>, are investigated by XRD, VT-EPR, UV-vis, electrochemical, kinetic, and DFT methods. In solutions, both stereoisomers exist as open-shell singlets with Δ<i>E</i><sub>S-T</sub> = -3.1 and -3.8 kcal mol<sup>-1</sup>, respectively. The <i>anti</i> isomer was resolved into enantiomers and converts to <i>syn</i> with Δ<i>G</i><sup>‡</sup><sub>298</sub> = 23.6(8) kcal mol<sup>-1</sup>.
Authors
- Piotr Kaszyński (ORCID: https://orcid.org/0000-0002-2325-8560)
- Paulina Bartos (ORCID: https://orcid.org/0000-0003-0514-951X)
- Andrienne C. Friedli (ORCID: https://orcid.org/0000-0003-2429-3170)
- Dominika Pomikło (ORCID: https://orcid.org/0000-0003-1297-8922)
- Oleksandr Hietsoi (ORCID: https://orcid.org/0000-0003-0332-1064)
- Kadin B. Sorenson
Institutions
- Middle Tennessee State University (US)
- University of Łódź (PL)
- Centrum Badań Molekularnych i Makromolekularnych Polskiej Akademii Nauk (PL)
- Polish Academy of Sciences (PL)
Publication Details
- Journal
- Journal of the American Chemical Society
- Published
- 2024-12-20
- DOI
- https://doi.org/10.1021/jacs.4c16500
- Citations
- 5
- Primary Topic
- Synthesis and Properties of Aromatic Compounds
- Type
- article
- Field-Weighted Citation Impact
- 1.25
Funders
- Narodowe Centrum Nauki
- Division of Undergraduate Education