Synthesis and stereochemistry of highly unsymmetric beta,meso-linked porphyrin arrays.
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.
Götz
Daniel C G
DC
Institute of Organic Chemistry and Rontgen Research Center for Complex Material Systems, University of Würzburg, Am Hubland, D-97074 Würzburg, Germany.
Bruhn
Torsten
T
Senge
Mathias O
MO
Bringmann
Gerhard
G
D009682:Magnetic Resonance Spectroscopy; D011166:Porphyrins / Q000138:chemical synthesis* / Q000737:chemistry; D013056:Spectrophotometry, Ultraviolet; D013237:Stereoisomerism; D013696:Temperature
D011166:Porphyrins