Synthesis of a Linear Assembly Consisting of a Central Ru(Phen)32+ Derivative and Two Peripheral Porphyrins

Salom‐Roig, Xavier J.; Chambron, Jean‐Claude; Goze, Christine; Heitz, Valérie; Sauvage, Jean‐Pierre

doi:10.1002/1099-0690(200210)2002:19<3276::aid-ejoc3276>3.0.co;2-r

Cited by 12 publications

(7 citation statements)

References 9 publications

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“…Compound 4 22 was first alkylated to produce aldehyde 5, which then reacted with 6 23 and pyrrole in refluxing propionic acid to afford porphyrin 8. 24 The latter was then hydrolyzed with sodium hydroxide and further converted to acyl chloride 10 with thionyl chloride. Treatment of 10 with 11 25 and (HR) mass spectroscopy or microanalysis and are of good solubility in organic solvents such as chloroform and toluene.…”

Section: Resultsmentioning

confidence: 99%

“…The emission of the porphyrin units of Zn 3 3 could not be quenched completely even in the presence of excessive 24, 19l which may be rationalized by considering that the complexation is a dynamic process and there is always a small amount of free Zn 3 3 in the solution. On the basis of the change of the emission strength at 606 nm with [24], the K a of complex Zn 3 3‚24 was evaluated to be 3.4 ((0.4) × 10 8 M -1 . 39 For the sake of comparison, the K a of complex Zn 2 1‚25 in Given the strong complexing feature between the foldamerbased porphyrin tweezers and the fullerene guests, the possibility of supramolecular chiral induction through complexation of the foldamer receptors toward chiral C 60 derivative 29 was explored.…”

Section: Resultsmentioning

confidence: 99%

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Hydrogen-Bonding-Driven Preorganized Zinc Porphyrin Receptors for Efficient Complexation of C₆₀, C₇₀, and C₆₀Derivatives

Shao

et al. 2005

J. Am. Chem. Soc.

148

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This paper describes the self-assembly of a new class of foldamer-based molecular tweezers, whose rigid folded conformations are stabilized by intramolecular hydrogen bonding. Two zinc porphyrin units are introduced to the ends of molecular tweezers Zn(2)1 and Zn(2)2, while three zinc porphyrin units are incorporated to the S-shaped bi-tweezers Zn(3)3, which may be regarded as a combination of two Zn(2)1 molecules. Due to the preorganized U-shaped feature, Zn(2)1 and Zn(2)2 are able to strongly complex C60, C70, and C60 derivative 25 in chloroform or toluene in a 1:1 binding stoichiometry, whereas Zn(3)3, which possesses two tweezer units, complexes the guests in a 1:2 stoichiometry. More stable complex Zn(3)3.24 is formed between Zn(3)3 and 24, a linear molecule bearing two C60 moieties at the ends, as a result of the cooperative interaction of two binding sites. Chiral induction is observed for all the three receptors upon complexation with C60-incoporated chiral phenylalanine derivative 29, although the complexation of 29 by the folding receptors is pronouncedly weaker than that of C60 and 25 due to increased steric hindrance. The driving force for the formation of the complexes is the well established pi-pi stacking between the zinc porphyrin and fullerene units. The 1H and 13C NMR, UV-vis, fluorescent, and circular dichroism spectroscopy have been used to investigate the complexing behavior of the folding receptors and the fullerene guests. The association constants of the corresponding complexes in toluene and chloroform (if possible) have been evaluated with the UV-vis and fluorescent titration experiments.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Hydrogen-Bonding-Driven Preorganized Zinc Porphyrin Receptors for Efficient Complexation of C₆₀, C₇₀, and C₆₀Derivatives

Shao

et al. 2005

J. Am. Chem. Soc.

148

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“…14 Similar isostructural trans-RuCl 2 (L) 4 complexes were obtained with L ) 4-formylpyridine, 105 pyrazine, 106 and mono-pyridylporphyrin. 107 Finally, refluxing 8 in acetonitrile yielded RuCl 2 (CH 3 CN) 4 of undisclosed (but probably trans) geometry, [108][109][110] which was then used as Ru precursor.…”

Section: Chartmentioning

confidence: 99%

Synthesis and Reactivity of Ru-, Os-, Rh-, and Ir-Halide−Sulfoxide Complexes

2004

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“…A mixed-aldehyde condensation of α-bromo- p -tolualdehyde ( 6 ), mesitaldehyde, and pyrrole afforded the desired A 3 B-porphyrin 7 bearing one bromomethylphenyl group in 16% yield. This valuable porphyrin building block, as with other bromomethylporphyrins, can be functionalized with a wide variety of nucleophiles. For example, treatment of 7 with triethyl phosphite in an Arbuzov reaction or sodium diethyl phosphite in THF gave porphyrin 4 in 80% or 73% yield, respectively.…”

Section: Resultsmentioning

confidence: 99%

Porphyrins Bearing Mono or Tripodal Benzylphosphonic Acid Tethers for Attachment to Oxide Surfaces

et al. 2003

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The ability to attach redox-active molecules to oxide surfaces in controlled architectures (distance, orientation, packing density) is essential for the design of a variety of molecular-based information storage devices. We describe the synthesis of a series of redox-active molecules wherein each molecule bears a benzylphosphonic acid tether. The redox-active molecules include zinc porphyrins, a cobalt porphyrin, and a ferrocene-zinc porphyrin. An analogous tripodal tether has been prepared that is based on a tris[4-(dihydroxyphosphorylmethyl)phenyl]-derivatized methane. A zinc porphyrin is linked to the methane vertex by a 1,4-phenylene unit. The tripodal systems are designed to improve monolayer stability and ensure vertical orientation of the redox-active porphyrin on the electroactive surface. For comparison purposes, a zinc porphyrin bearing a hexylphosphonic acid tether also has been prepared. The synthetic approaches for introduction of the phosphonic acid group include derivatization of a bromoalkyl porphyrin or use of a dimethyl or diethyl phosphonate substituted precursor in a porphyrin-forming reaction. The latter approach makes use of dipyrromethane building blocks bearing mono or tripodal dialkyl phosphonate groups. The zinc porphyrin-tripodal compound bearing benzylphosphonic acid legs tethered to a SiO(2) surface (grown on doped Si) was electrically well-behaved and exhibited characteristic porphyrin oxidation/reduction waves. Collectively, a variety of porphyrinic molecules can now be prepared with tethers of different length, composition, and structure (mono or tripodal) for studies of molecular-based information storage on oxide surfaces.

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Synthesis of a Linear Assembly Consisting of a Central Ru(Phen)32+ Derivative and Two Peripheral Porphyrins

Cited by 12 publications

References 9 publications

Hydrogen-Bonding-Driven Preorganized Zinc Porphyrin Receptors for Efficient Complexation of C₆₀, C₇₀, and C₆₀Derivatives

Hydrogen-Bonding-Driven Preorganized Zinc Porphyrin Receptors for Efficient Complexation of C₆₀, C₇₀, and C₆₀Derivatives

Synthesis and Reactivity of Ru-, Os-, Rh-, and Ir-Halide−Sulfoxide Complexes

Porphyrins Bearing Mono or Tripodal Benzylphosphonic Acid Tethers for Attachment to Oxide Surfaces

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Synthesis of a Linear Assembly Consisting of a Central Ru(Phen)32+ Derivative and Two Peripheral Porphyrins

Cited by 12 publications

References 9 publications

Hydrogen-Bonding-Driven Preorganized Zinc Porphyrin Receptors for Efficient Complexation of C60, C70, and C60Derivatives

Hydrogen-Bonding-Driven Preorganized Zinc Porphyrin Receptors for Efficient Complexation of C60, C70, and C60Derivatives

Synthesis and Reactivity of Ru-, Os-, Rh-, and Ir-Halide−Sulfoxide Complexes

Porphyrins Bearing Mono or Tripodal Benzylphosphonic Acid Tethers for Attachment to Oxide Surfaces

Contact Info

Product

Resources

About

Hydrogen-Bonding-Driven Preorganized Zinc Porphyrin Receptors for Efficient Complexation of C₆₀, C₇₀, and C₆₀Derivatives

Hydrogen-Bonding-Driven Preorganized Zinc Porphyrin Receptors for Efficient Complexation of C₆₀, C₇₀, and C₆₀Derivatives