Eugene LeGoff

Oxidation of furans II. Use of furans as masked dienophiles in the intramolecular diels-alder reaction

Abstract Chemoselective oxidation of alkadienylfurans using m -chloroperoxy-benzoic acid gave trienes which underwent intramolecular Diels-Alder cycloaddition to hydrindenones.

A Facile Synthesis of 1,4-Diketones from Organolithium Reagents and N,N,N′,N′-Tetramethylsuccinamide

Abstract The reaction of organolithium reagents (alkyl, aryl, heteroaryl) with N,N,N′,N′-tetramethylsuccinamide at 0 °C gives good yields of the corresponding 1,4-diketones.

Intercalation of polyfuran in FeOCl.

Abstract The intercalation of polyfuran, by in-situ intercalative oxidative polymerization of terfuran in FeOCl is reported. The intercalation reaction proceeds to completion in methanol in a sealed tube at 100 °C. The resulting compound, polyfuran/FeOCl (I), is crystalline. An interlayer expansion of ≈7.7 A is observed upon intercalation. The formation of polyfuran in the interlayer space of the host material was confirmed by FTIR spectroscopy and by isolation of the polymers from the host. Tetrafuran could not be intercalated completely under the conditions employed. Electrical conductivity and thermoelectric power data from pressed pellets of (I) are reported and the results are compared with other FeOCl intercalated polymers. X-ray diffraction, magnetic, infrared spectroscopic and scanning and transmission electron microscopic characterization of (I) are reported.

Synthesis of Octasubstituted Porphyrins

Abstract The synthesis of porphyrins having high solubility in organic solvents requires the presence of long chain aliphatic substituents. Such substituted porphyrins are readily prepared in good yields by extension of our general procedure1 which involves the synthesis of α,β-unsaturated ketones, conversion of these to 3,4-disubstituted pyrroles followed by acid catalyzed condensations of these pyrroles with formaldehyde in the presence of air.

Electrochemical synthesis and electronic properties of poly(3,4-dibutyl-α-terthiophene)

Abstract Electrochemically prepared poly(3,4-dibutyl-α-terthiophene) has been investigated and the relationship between the electronic properties, the chemical structure of the monomer and the electrolyte used during the electropolymerization was studied. Doping studies were carried out with various electrolytes. We have electrochemically oxidized (p-doping) and reduced (n-doping) thin films of this polymer on platinum electrode under the same electrochemical conditions. We find that the films show a reversible oxidation wave yielding an electrically conducting polymer and a reversible reduction wave which is sensitive to the nature of the electrolyte. A value for the band gap derived electrochemically compares well with that obtained by optical absorption measurements and X-ray photoelectron spectroscopy. The electrical conductivity varies by 10 12 S cm −1 between the doped and undoped states of the polymer. The temperature-independent magnetic susceptibility above 100 K is consistent with the conducting properties of this polymer. The electrochemically prepared material is compared with the chemically prepared one using the same monomer.

Poly (3',4'-dibutyl-α-terthiophene-phenylene-vinylene) : a new soluble and dopable phenylene-vinylene-based conjugated polymer

Abstract A new soluble and dopable copolymer consisting of 3′,4′-dibutyl-2,2′:5′,2″-terthiophene and phenylene-vinylene units has been designed and prepared via a Wittig reaction. This title copolymer is soluble in common organic solvents such as THF and CHCl 3 , and can be doped with iodine achieving an electrical conductivity of about 3.2 × 10 −2 S/cm at room temperature. Films of this copolymer are electroactive and turn reversibly and rapidly from red to green-blue upon doping and undoping electrochemically.

Condensation of o-phenylenediamine with trans-dibenzoylethylene synthesis of 2, 5-diphenyl-1, 6-dihydro-1, 6-benzodiazocine

Beim Erhitzen von o-Phenylendiamin (I) mit Dibenzoylathylen (II) in siedender Essigsaure bildet sich ein Gemisch der Verbindungen (III)-(VII), wahrend in siedendem Athanol in Gegenwart von 5% Essigsaure nur das Phenylchinoxalin (VI) in 90%iger Ausbeute erhalten wird.

Conjugated Polymers in Layered Hosts: Formation of Emeraldine Salt and Polyfuran in FeOCl

Electrically conducting polymers have received a great deal of attention due to their promising electrical properties and potential applications1, 2. Our understanding of the structure of these systems is still fragmentary due to their quasi-crystalline nature and insolubility in common organic solvents. Important structural problems associated with single chain and their macromolecular aggregation remain to be solved. The systematic control and modification of their physical, structural and electronic properties is an active area of research. Goals include the optimization of the charge transport properties and the better understanding of the relationship between electronic and lattice structure.