Synthese und Redoxeigenschaften von Verbindungen mit mehreren separaten anthracen‐Elektrophoren

Fiedler, Jürgen; Hubery, Walter; Müllen, Kläus

doi:10.1002/ange.19860980509

Angewandte Chemie

1986

DOI: 10.1002/ange.19860980509

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Synthese und Redoxeigenschaften von Verbindungen mit mehreren separaten anthracen‐Elektrophoren

Jürgen Fiedler

Walter Hubery

Kläus Müllen

Abstract: Bei der Konfigurationszuordnung hilft der Anisotropieeffekt der SulfinylgrupperX1: DaB die Methylprotonen von 4a (6=2.51, s) und die ortho-Arylprotonen von 4b (6=7.93, m) bei relativ tiefem Feld absorbieren, zeigt, daI3 der Sauerstoff der SO-Gruppe diesen Substituenten nahe ist. d. h. die C=S-Bindung ist E-konfiguriert. Dagegen scheint bei den Anilinderivaten 4c die Z-Form zu dominieren (siehe Tabelle 1). 9 Abb. 1. ORTEP-Plot der Struktur von 4b im Kristall. Die Schwingungsellipsoide entsprechen einer 50proz. … Show more

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Cited by 23 publications

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“…(3) No contacts smaller than the van der Wads distances are found between lithium ions and carbon centers of the fluorenyl moieties. The shortest distances d(Li-C) are 436 pm in 1 and 442 pm in 2 (4). In the crystal lattice of 2, the Li-Li distances (less than 1000 pm) are 756, 852, and 870 pm, the intramolecular C9-C9 distances 888 and 896 pm, and the intermolecular C9-C9 distances 770 pm.…”

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confidence: 94%

The Structures of 1,n‐Bis(9‐lithio‐9‐fluorenyl)ethane · 8 THF and ‐hexane · 8 THF as Models for Solvent‐Separated Ion Pairs

Becker

Enkelmann

Müllen

1989

Angew. Chem. Int. Ed. Engl.

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increased up to 60%; similar yields are obtained by adding methylltthium to 7. Compound Ic is storable under nitrogen at -20'C. 6 : A 1 . 6~ solution of nBuLi in hexane (310mL) was added to hexyl-(tripheny1)phosphonium chloride (215 g, 0.50 mol, Aldrich) in 1 L of dlethyl ether at 20 'C. The clear, dark red solution was cooled to -65 "C and treated over 2 h with a solution of 5 (65 g. 0.50 mol) in 1 L of ether. The resulting precipitate was filtered off under suction at low temperature, the solvent was removed, and the residue was distilled (b.p. 50"CiO.l Pa: yield 50-60 g. 51 -7: A solution of 6 (48 g, 0.25 mol) and bromoform (80 g, 0.3 mol) in 80 mL of dichloromethane was treated at room temperature with 0.8g of trimethyl(phenyl)ammonium chloride and 0.8 mL of ethanol. A 50% solution of sodium hydroxide (80 mL) was then added dropwise to the stirred solution. After stirring for 3 d, the reaction mixture was subjected to aqueous workup. Vacuum distillation (0.1 Pa. bath at 110'C) afforded reusable starting material and 7 as a colorless liquid (b.p. 95 'C/O.l Pa; yield 42 g. 46%, yield when 6 was reused. 90X). 61 %).

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mentioning

confidence: 94%

The Structures of 1,n‐Bis(9‐lithio‐9‐fluorenyl)ethane · 8 THF and ‐hexane · 8 THF as Models for Solvent‐Separated Ion Pairs

Becker

Enkelmann

Müllen

1989

Angew. Chem. Int. Ed. Engl.

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Polaron migration in doped polysilanes: am i calculations on the radical cation Si₁₇(CH₃)₃₆⁺

1995

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In conclusion, we have prepared Hg-1223 with 60-70% phase purity by a simplified route. The material prepared in this way shows a sharp onset of diamagnetism at a T, of 135 K. In addition, HREM has shown this sample to be of good quality with a lack of observable defects, possibly explaining the sharpness of the superconducting transition. The preparation was carried out in a single-step route from mono-oxides, allowing us the flexibility provided by airstable starting materials. With the difficulty in preparing good quality precursors reported by many, the preparation of Hg-1223 in a single-step reaction is significant in itself, and we have shown here that once this approach is adopted, the synthesis itself becomes relatively simple. E-xperimen talMono-oxides (all > 99% purity) were ground in appropriate molar quantities. Powder mixing was generally carried out in an argon-filled glovebox to minimize moisture, CO, absorption etc. (however, in our experience powder preparation in air can also yield high-quality samples). The resulting mixtures were pressed into pellets (under a pressure of 3 tonnes) which wrere wrapped in silver foil and air-sealed with a bench-torch in quartz tubes (od = 16 mm, id = 13 mm). The sealed tubes were contained in steel bombs, placed in a furnace, and heated at rates between 100 and 700 "C/h to temperatures between 650 and 800 'C. Temperatures were maintained for 5-10h, after which samples were left to cool at the natural rate of the furnace. In order to gain maximum T,s a post-anneal of the pellets was generally carried out in flowing 0, at 300 'C for 15 h.Characterization was performed by powder X-ray diffraction on a Siemens D5000 diffractometer (Cu-K,, radiation). Magnetic measurements were performed on a Cryogenics S100 SQUID and Lake Shore AC susceptibility rig. EDS was carried out on a JEOL 2010cx electron microscope. High-resolution electron microscopic (HREM) images were obtained using a JEOL 200cx electron microscope.

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Poly(anthrylentrimethylene) und 9,10‐überbrückte Anthracene durch reduktive Alkylierung

1986

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Synthese und Redoxeigenschaften von Verbindungen mit mehreren separaten anthracen‐Elektrophoren

Cited by 23 publications

References 12 publications

The Structures of 1,n‐Bis(9‐lithio‐9‐fluorenyl)ethane · 8 THF and ‐hexane · 8 THF as Models for Solvent‐Separated Ion Pairs

The Structures of 1,n‐Bis(9‐lithio‐9‐fluorenyl)ethane · 8 THF and ‐hexane · 8 THF as Models for Solvent‐Separated Ion Pairs

Polaron migration in doped polysilanes: am i calculations on the radical cation Si₁₇(CH₃)₃₆⁺

Poly(anthrylentrimethylene) und 9,10‐überbrückte Anthracene durch reduktive Alkylierung

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Synthese und Redoxeigenschaften von Verbindungen mit mehreren separaten anthracen‐Elektrophoren

Cited by 23 publications

References 12 publications

The Structures of 1,n‐Bis(9‐lithio‐9‐fluorenyl)ethane · 8 THF and ‐hexane · 8 THF as Models for Solvent‐Separated Ion Pairs

The Structures of 1,n‐Bis(9‐lithio‐9‐fluorenyl)ethane · 8 THF and ‐hexane · 8 THF as Models for Solvent‐Separated Ion Pairs

Polaron migration in doped polysilanes: am i calculations on the radical cation Si17(CH3)36+

Poly(anthrylentrimethylene) und 9,10‐überbrückte Anthracene durch reduktive Alkylierung

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Polaron migration in doped polysilanes: am i calculations on the radical cation Si₁₇(CH₃)₃₆⁺