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Synfacts 2013; 9(1): 0042
DOI: 10.1055/s-0032-1317882
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart · New York

Nitrogen-Free [18]Porphyrinoids in Two Steps

Contributor(s):
Timothy M. Swager
,
Jonathan G. Weis
Lash TD, * Lammer AD, Ferrence GM. Illinois State University, Normal, USA
Two-Step Synthesis of Stable Dioxadicarbaporphyrins from Bis(3-indenyl)methane.

Angew. Chem. Int. Ed. 2012;
51: 10871-10875
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Further Information

Publication History

Publication Date:
17 December 2012 (online)

 
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Key words

carbaporphyrins - fulvenes - indenes

Significance

The researchers synthesized substituted and unsubstituted dioxadicarbaporphyrins, which are the first examples of porphyrinoids with adjacent indenes. Bis(3-indenyl)methane 1 was reacted with various aryl aldehydes to yield compounds 3. Reaction with formaldehyde or an aryl aldehyde followed by oxidation led to the formation of dioxadicarbaporphyrins 5 and 6, respectively. These bilin analogues are interesting as natural products as well as organic opto-electronic materials.


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Comment

The reaction of bis(3-indenyl)methane 1 with aryl aldehydes was expected to give a symmetric difulvene; however, the fully conjugated ­derivative 3 was obtained instead and confirmed with 2D NMR and X-ray crystallography. The 1H NMR spectra of the porphyrinoids 5 and 6 displayed that the macrocycles are diatropic, as ­expected from the [18]annulene core.


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