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Synfacts 2009(6): 0615-0615  
DOI: 10.1055/s-0029-1216656
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart ˙ New York

Nanostructures from Self-Assembled Porphyrin Bilayers

Contributor(s): Timothy M. Swager, Jason R. Cox
C. Huang, L. Wen, H. Liu, Y. Li*, X. Li, M. Yuan, J. Zhai, L. Jiang, D. Zhu
Beijing National Laboratory for Molecular Sciences, P. R. of China
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Publication History

Publication Date:
25 May 2009 (online)

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Significance

The porphyrin triad bearing flexible carbazole linkers was synthesized via a MacDonald-type [2+2] condensation followed by Suzuki coupling, reductive ring closure and substitution using carbazole nitrogen as nucleophile. The carbazole linker allows the triad to form a ”U" shape that is capable of forming dense bilayer structures upon self-assembly in dichloro­methane-methanol solutions. The bilayer structures are capable of forming vesicles, which can build higher-dimensional structures upon heating.