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New porphyrinoids, 9. Synthesis of a bisvinylogous porphyrin with a [22] annulene system

✍ Scribed by Gosmann, Martin ;Vogt, Andreas ;Franck, Burchard

Publisher
John Wiley and Sons
Year
1990
Tongue
English
Weight
618 KB
Volume
1990
Category
Article
ISSN
0947-3440

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✦ Synopsis

Abstract

The twofold vinylogously enlarged porphyrin with a 22‐π‐electron system 3 was prepared by vinylogous bisformylation of the dipyrrylmethane 7 to give 8 and subsequent acid‐catalyzed condensation of 8 with 7. The [22]porphyrin 3 is characterized by a Soret band at 469 nm, which on protonation of the porphyrinoid becomes very narrow with the highest extinction coefficient so far observed for an organic pigment (ϵ = 1090000). In the ^1^H‐NMR spectrum 3 reveals a strong diamagnetic ring‐current effect with a shift difference between inner and outer protons of Δδ = 20.1 ppm, thereby proving itself a pronounced aromatic system.

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