Chemical Constitution and Activity of Bipyridylium Herbicides. XII. Diquaternary Salts of 6-Methyl-2,2'-bipyridyl and 2-Methyl-4,4'-bipyridyl

Schmalzl, K. J.; Summers, L. A.

doi:10.1071/ch9770657

Cited by 32 publications

(9 citation statements)

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“…Viologen‐type organic electrochromic (EC) compounds of interest have been widely investigated because of their various application fields, such as herbicides, photonic sensors, electron transfer devices, displays, and antiglare mirrors . EC materials show color changes from clear to three primary colors, red, green, and blue, which is required to realize full color in electronic paperlike imaging devices.…”

Section: Introductionmentioning

confidence: 99%

Organic multiviologen electrochromic cells for a color electronic display application

Chen

Yeh³

2014

J of Applied Polymer Sci

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The electrochromic (EC) and optical properties of three new viologen compounds containing 1,1 0 -di-n-heptyl-4,4 0 -bipyridinum dibromide (DHBPDB; C 24 H 38 Br 2 N 2 ), 1-heptyl-4-(4-pyridyl)pyridinium bromide (HPPB; C 17 H 23 BrN 2 ), and 1,1 0 -dis-(p-cyanophenyl)-4,4 0 -bipyridinium chloride (DCBPC; C 12 H 8 N 2 OBr 2 ) for potential use in electrochromism applications were investigated. The repetitive stability of all of the EC cells could be improved through the addition of ferrocene as an electron donor (a counter redox material) to the electrolyte solution under several redox cycles. The experimental results demonstrate that the EC cell showed a reversible color change from clear (tintless) to three different colors with the application of electrochemical stimuli at specific potentials. The color of the EC cells turned red, green, or blue upon electrochemical reduction for DHBPDB, HPPB, and DCBPC in indium tin oxide sandwich-type cells. Because of the different viologen molecules competing to capture electrons and affecting the EC efficiency and life of the multiviologen cells, they could be improved by the optimization of the working voltage in the multiviologen cells from the modification of an operative potential based on the cyclic voltammetry measurements. In this article, we propose a prototype device of multicolor electrochromic display, which provides potential application for multicolor electronic displays or EC paper.

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Section: Introductionmentioning

confidence: 99%

Organic multiviologen electrochromic cells for a color electronic display application

Chen

Yeh³

2014

J of Applied Polymer Sci

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“…Viologens, which are 1,1′‐disubstituted 4,4′‐bipryidinium dications, are electrochromic materials of interest in various application fields, such as herbicides, photonic sensors, electron transfer devices, and antiglare mirrors 1–5. Viologens naturally stay in a dication state without an applied potential, and this results in transparency.…”

Section: Introductionmentioning

confidence: 99%

Preparation of a multicolored reflective electrochromic display based on monodisperse polymeric microspheres with N‐substituted viologen pendants

Ryu

Lee

Suh

2007

J of Applied Polymer Sci

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This article describes the preparation of multicolored reflective electrochromic displays (R-ECDs) through the control of the substituents on viologen molecules. Cyanophenyl, salicylic, and alkyl groups were introduced onto 4,4 0 -bipyridine. The synthesized viologen moieties were reacted with methyl chloride functional groups on polymeric microspheres, which were prepared by seeded polymerization. Then, R-ECD cells were fabricated by the placement of a mixture of the viologen-modified polymeric microspheres and an electrolyte between sandwiched indium tin oxide glasses. The R-ECDs showed an inherent white background without potential because the micrometer-range particles scattered the light, and the viologen was in a bleached state. From spectrophotometric results and visual appearances, it was confirmed that the devices showed red, green, and blue colors with respect to cyanophenyl-, salicylic-, and alkyl-substituted viologen pendants when 2.7 V was applied to the device.

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“…Preparation of 2-Aryl-3-aminoprop-2-enoic Acids 7a-g. The l,3-oxazin-6-one 6 (0.5 (5) Eiden, F.; Nagar, B. S. Naturwissenschaften 1963, 50, 403. (7) Marx, J. N.; Argyle, J. C.; Norman, L. R. J.…”

Section: Methodsmentioning

confidence: 99%

“…To our knowledge, no optically active title compounds have been reported in the literature so far; even monoalkyl-substituted 2,2/-bipyridines are very seldom described. [4][5][6] In this paper the results obtained in the synthesis of (+)-(S)-2-(2'-pyridyl)-6- (1) and (+)-(S)-2-(2'-pyridyl)-4sec-butylpyridine (2) are presented.…”

Section: Methodsmentioning

confidence: 99%

“…The reaction was cooled to room temperature and 9 equiv of KO-t-Bu was added, and the reaction was refluxed for 1 h. Workup as before gave the olefins. 5-Butyltetradec-5-ene (21). Title compound produced in 19% yield: nD20 1.4495; NMR 5.17 (t, 1 H, J = 7.0 Hz), 2.21-1.70 (m, 6 ), 1.26 (bs, 20 ), 1.05-0.73 (m, 9 H); 13C NMR 139.5, 124.8, 36.8, 32.0, 30.9, 30.6, 30.3, 29.8, 29.6, 29.4, 27.8, 23.0, 22.8, 22.6,14.1; MS, 252 (25), 55 (100).…”

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confidence: 99%

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Oxidation of 4-aryl-substituted isoxazolin-5-ones. A new synthesis of 2,5-diaryl-1,3-oxazin-6-ones

Beccalli¹,

Rosa²,

Marchesini³

1984

J. Org. Chem.

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Chemical Constitution and Activity of Bipyridylium Herbicides. XII. Diquaternary Salts of 6-Methyl-2,2'-bipyridyl and 2-Methyl-4,4'-bipyridyl

Abstract: Die Titelverbindungen (III) (verwandt dem Herbizid Diquat) und (VI) (verwandt dem Herbizid Paraquat) werden dargestellt.

Cited by 32 publications

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Organic multiviologen electrochromic cells for a color electronic display application

Organic multiviologen electrochromic cells for a color electronic display application

Preparation of a multicolored reflective electrochromic display based on monodisperse polymeric microspheres with N‐substituted viologen pendants

Oxidation of 4-aryl-substituted isoxazolin-5-ones. A new synthesis of 2,5-diaryl-1,3-oxazin-6-ones

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