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- W2004197441 abstract "Metalloporphyrins bearing two crown ether moieties (benzo-15-crown-5) at the 5- and 15-postions have been prepared by condensation of 4′-formyl-benzo-15-crown-5 with either unsubstituted or meso-aryl-substituted dipyrromethanes, followed by oxidation and metallation. The meso-meso-coupled ZnII diporphyrin Zn4 was prepared by the oxidative coupling of Zn1 with AgPF6. UV/vis, fluorescence, and 1H NMR spectroscopic studies revealed that addition of K+ and Rb+ to solutions of monomeric porphyrin derivatives M1 (M = 2 H, Zn, Co, Ni, Pd, Cu) in CHCl3:MeCN (2:1 v/v) induced face-to-face dimerization with high stability constants (ca. 1015−1019 M−3). 1H NMR analysis showed that the two Zn1 molecules in the face-to-face dimer were packed more closely than in TPP-type ZnII porphyrin bearing four crown ethers (Krishnan et al, J. Am. Chem. Soc. 1982, 104, 3643), but such dimerization was hardly detected for 10,20-diphenylated ZnII porphyrin Zn2, probably due to steric hindrance exerted by the meso phenyl groups. meso-Monoarylated ZnII porphyrin Zn3 exhibited a comparably large stability constant for formation of the face-to-face dimer with the meso-aryl substituents pointing outward. Coordination of 4-dimethylaminopyridine to CoII porphyrin was shown to be stronger than the interaction of K+ with the crown ether, thereby dissociating the face-to-face dimer (Co1)2 into six-coordinated monomeric CoII porphyrin 5. The diporphyrin Zn4 formed extended linear aggregates upon addition of K+ and Rb+, owing to the divergent disposition of the crown ether substituents. (© Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)" @default.
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- W2004197441 date "2002-04-01" @default.
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- W2004197441 title "Control ofFace-to-face and Extended Aggregations of Crown Ether-Appended Metalloporphyrins" @default.
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- W2004197441 doi "https://doi.org/10.1002/1099-0690(200204)2002:7<1197::aid-ejoc1197>3.0.co;2-j" @default.
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