Synthesis and stereochemistry of highly unsymmetric β,meso-linked porphyrin arrays

Journal of Organic Chemistry

Volumn 74, Issue 21, 2009, Pages 8005-8020

  Göotz, Daniel C G ^a   Bruhn, Torsten ^a   Senge, Mathias O ^b   Bringmann, Gerhard ^a  

^a UNIVERSITY OF WÜRZBURG   (Germany)

^b TRINITY COLLEGE DUBLIN   (Ireland)

Author keywords

[No Author keywords available]

Indexed keywords

BUILDING BLOCKES; CHEMICAL EQUATIONS; MULTICHROMOPHORES; PHOTOPHYSICAL PROPERTIES; PORPHYRIN ARRAYS; SUZUKI-TYPE COUPLING; SYNTHETIC PROCEDURES; THREE DIMENSIONAL GEOMETRY;

CHEMICAL BONDS; CHEMICAL REACTIONS; NONLINEAR OPTICS; ORGANIC POLYMERS; STEREOCHEMISTRY;

PORPHYRINS;

PORPHYRIN;

ARTICLE; CHIRALITY; CHROMATOPHORE; NANOARRAY; NANOFABRICATION; OPTICS; STEREOCHEMISTRY; SUBSTITUTION REACTION; SUZUKI REACTION;

MAGNETIC RESONANCE SPECTROSCOPY; PORPHYRINS; SPECTROPHOTOMETRY, ULTRAVIOLET; STEREOISOMERISM; TEMPERATURE;

EID: 70350705896     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo901483q     Document Type: Article

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174. 67
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177. +] 1315.5205, found 1315.5205.
178. 1H NMR, as would have been expected for the two resulting diastereomers S,M-9f and S,P-9f. Most probably, the position of the stereocenter is too peripheral to influence, e.g., the protons of the central C20′-phenyl moiety.
179. For a recent review on porphyrin bioconjugates, see: (a) Hudson, R.; Boyle, R. W. J. Porphyrins Phthalocyanines 2004, 8, 954-975 and references cited therein.
180. For some recent, selected publications on porphyrin bioconjugates, see: (b) Sutton, J. M.; Fernandez, N.; Boyle, R. W. J. Porphyrins Phthalocyanines 2000, 4, 655-658.
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188. (j) Sibrian-Vazquez, M.; Nesterova, I. V.; Jensen, T. J.; Vicente, M. G. H. Bioconjugate Chem. 2008, 19, 705-713.
189. For selected reviews on dendrimeric porphyrins, see: (a) Venturi, M.; Serroni, S.; Juris, A.; Campagna, S.; Balzani, V. Top. Curr. Chem. 1998, 197, 193-228.
190. (b) Jiang, D.-L.; Sadamoto, R.; Tomioka, N.; Aida, T. In Hyper-Struct. Mol. I; Sasabe, H., Ed.; Taylor & Francis, CRC Press: Boca Raton, FL, 1999; pp 63-73.
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194. 3 signal.
195. This assumption is affirmed by the fact that, in the course of our investigations, RI-PBE-D/SV(P) calculations of a dimeric model system predicted the existence of two main tautomers (regarding the NH protons of the β-linked porphyrin macrocycle) in a ratio of 1:2.8 in the gas phase. Detailed investigations on this phenomenon are in progress.