A rectangular hexaphyrin bearing outer straps at the long side has been synthesized by SNAr reaction of hexaphyrin with allyl alcohol, intramolecular olefin metathesis by using Hoveyda-Grubbs second-generation catalyst, and reduction with NaBH4. The peripheral straps enforce a rectangular conformation for the hexaphyrin, which shows Hückel antiaromatic character, as confirmed by its planar X-ray structure, a strong paratropic ring current, characteristic UV/Vis/NIR absorption features, small electrochemical HOMO-LUMO gap, and very fast S1 decay.
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© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
All Science Journal Classification (ASJC) codes
- Organic Chemistry