A Modular Synthesis of Planar, Redox-Stable Hückel Anti-Aromatic [36]Nonaphyrin (1.0.0.1.0.0.1.0.0) with Only Three
Jayaprakash Ajay1, Thondikkal Sulfikarali1, Aathira Edwin1
1Indian Institute of Science Education and Research Thiruvananthapuram, Vithura, Kerala 695551, India.
Abstract:
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 (SN) and [48]dodecaphyrin (SN). The single crystal X-ray structure of SN revealed a perfectly planar conformation. Various spectroscopic and DFT analyses unambiguously confirmed the strong anti-aromatic feature of SN, and the large expanded congener SN displayed a nonplanar conformation with weak anti-aromaticity.
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