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American Chemical Society, Journal of Organic Chemistry, 21(74), p. 8005-8020, 2009

DOI: 10.1021/jo901483q

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Synthesis and Stereochemistry of Highly Unsymmetric β,Meso-Linked Porphyrin Arrays

Journal article published in 2009 by Daniel C. G. Götz, Torsten Bruhn, Mathias O. Senge ORCID, Gerhard Bringmann
This paper is available in a repository.
This paper is available in a repository.

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Abstract

Porphyrin arrays with tailor-made photophysical properties and well-defined three-dimensional geometries constitute attractive synthetic targets in porphyrin chemistry. The paper describes a variable, straightforward synthetic procedure for the construction of beta,meso-linked porphyrin multichromophores in good to excellent yields. In a Suzuki-type coupling reaction beta-borylated 5,10,15,20-tetraarylporphyrins (TAPs) served as versatile building blocks for the preparation of a plethora of directly linked, unsymmetrically substituted di- and triporphyrins. Besides their interesting photophysical properties, especially the trimeric porphyrin arrays show exciting stereochemical features. The established protocols thus open a convenient entry into the synthesis of achiral and chiral, unsymmetrically substituted beta,meso-linked oligoporphyrins, e.g., for applications in biomedicine or nonlinear optics.