A Modular Synthesisof Planar, Redox-Stable HuckelAnti-Aromatic [36]Nonaphyrin (1.0.0.1.0.0.1.0.0) with Only Three <i>meso</i>-Bridges
A rigid dithienopyrrole (DTP) subunit was functionalized by taking advantage of the fused core, which upon Lewis acid-catalyzed self-condensation afforded two structurally distinct expanded porphyrinoids, namely [36]nonaphyrin (<b>S</b><sub><b>6</b></sub><b>N</b><sub><b>3</b></sub>) and [48]dodecaphyrin (<b>S</b><sub><b>8</b></sub><b>N</b><sub><b>4</b></sub>). The single crystal X-ray structure of <b>S</b><sub><b>6</b></sub><b>N</b><sub><b>3</b></sub> revealed a perfectly planar conformation. Various spectroscopic and DFT analyses unambiguously confirmed the strong anti-aromatic feature of <b>S</b><sub><b>6</b></sub><b>N</b><sub><b>3</b></sub>, and the large expanded congener <b>S</b><sub><b>8</b></sub><b>N</b><sub><b>4</b></sub> displayed a nonplanar conformation with weak anti-aromaticity.
Publication Details
- Journal
- Figshare
- Published
- 2025-02-21
- DOI
- https://doi.org/10.1021/acs.orglett.5c00170.s001
- Primary Topic
- Porphyrin and Phthalocyanine Chemistry
- Type
- article
- Field-Weighted Citation Impact
- 0.00