Effect of an Electric Field on the Growth and Optoelectronic Properties of Quasi-One-Dimensional Organic Single Crystals of 1-(Phenylazo)-2-naphthol

Liu, Chong Yang; Lynch, Vincent M.; Bard, Allen J.

doi:10.1021/cm9605025

Cited by 32 publications

(30 citation statements)

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“…In this case, electrons from the excited state of ZnODEP molecules are injected into the irradiated ITO contact ͑termed an anodic current͒ while positive charges move to the opposite electrode. 1,5,[7][8][9][10][11][12][13] The relation between I sc as a function of time without bias ͑the short-circuit photocurrent͒ from pixel 4D is shown in Fig. 2b.…”

mentioning

confidence: 99%

Addressing of Optoelectronic Memory of Thin Film Zinc Porphyrin with Crossed 5 μm Indium Tin Oxide Arrays

Liu

Bard²

2001

Electrochem. Solid-State Lett.

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We report here the preparation and characterization of an optoelectronic memory device based on a single layer of organic thin film ͑ϳ0.9 m thick͒ of zinc octakis͑␤-decoxyethyl͒porphyrin, sandwiched between two crossed indium tin oxide ͑ITO͒ arrays. The ITO lines in the array were 5 m wide and were separated from each other by a 5 m gap. Data ͑in the form of an electric charge͒ could be independently stored at and retrieved from an intersection of the crossed ITO lines with irradiation. Each intersection defined one memory pixel (5 ϫ 5 m) and there was no cross talk with nearby pixels under the test conditions, clearly demonstrating its potential application as an information storage device using a molecular thin film.Zinc octakis͑␤-decoxyethyl͒porphyrin ͑ZnODEP͒ is a flat molecule with eight long hydrocarbon chains. 1 In the crystal, molecules are regularly stacked to form individual columns and the nonionic alkyl tails serve as an insulating coating, leading to a bundle of electrically insulated one-dimensional molecular ''wires.'' 1 Even within the same molecular column, the intermolecule separation is ϳ4 Å, 1 significantly larger than those in inorganic substances. This produces an intrinsic characteristic of a crystal structure consisting of discrete molecules that can be considered an ''orientated molecular gas.'' 2,3 This structure has an inherent advantage over inorganic materials as a medium for high-density charge trapping and, therefore, information storage, because charge carriers are localized on individual molecules and can be trapped for long times on structural defects or impurity sites. [2][3][4] In principle, the theoretical size of one memory element could be as small as a single molecular column representing the ultimate density in data storage. 5, 6 We have demonstrated previously that an individual pixel could be as small as a few tens of nanometers with a configuration of a sharp scanning tunneling microscopy ͑STM͒ tip/organic film/indium tin oxide ͑ITO͒. 5,7 While this tip-type movable structure is simple and convenient for testing the possibility of ultrahigh density data storage, it is not useful for most memory applications where a fixed rigid device is more desirable. Nor is it useful in examining cross talk among different pixels. This led us to the present study of an alternative configuration as shown in Fig. 1, in which each 5 m wide ITO line served as an independent electrode and was individually externally addressable.When a bias voltage was applied to two of the crossed ITO fingers ͑such as column 3 and row D͒, the organic film was subjected to the electric field at only that particular intersection ͑desig-nated as pixel 3D͒. Thus, Fig. 1 illustrates a total of 25 memory elements. Figure 2a shows the current as a function of bias voltage from pixel 3D with and without irradiation. The dark current is negligible over the potential range of Ϫ1 to ϩ1 V. Essentially the same result was seen with the other pixels. Note that in this and other measurements discussed below, the whole fi...

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confidence: 99%

Addressing of Optoelectronic Memory of Thin Film Zinc Porphyrin with Crossed 5 μm Indium Tin Oxide Arrays

Liu

Bard²

2001

Electrochem. Solid-State Lett.

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“…Recently we have shown [3] by theoretical calculations and by analysis of the existing crystallographic data of structurally similar compounds [4][5][6][7][8] that the structures of the enol and keto tautomers of 4-((2-hydroxynaphthalen-1-yl)diazenyl)-3,5-dinitrobenzoic acid as previously predicted by Adegoke are incorrect. In the same study [3] the tautomerism of 1-((2nitrophenyl)diazenyl)naphthalen-2-ol (1, Scheme 1) was investigated by using DFT calculations and UV-Vis spectroscopy.…”

Section: Introductionmentioning

confidence: 90%

4-Carboxyl-2,6-dinitrophenylazohydroxynaphthalenes tautomerism NMR re-explained and other methods verified

et al. 2017

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In two consecutive studies the tautomerism in 4-((2-hydroxynaphthalen-1-yl)diazenyl)-3,5dinitrobenzoic acid and the structurally similar 1-((2-nitrophenyl)diazenyl)naphthalen-2-ol has been considered from viewpoint of theoretical chemistry, UV-Vis spectroscopy and NMR.Although the theoretical data (at M062X level) show that both compounds exist only as a keto tautomer, the experiment proves existence of the enol form. The difference in the results obtained by UV-Vis spectroscopy and NMR requires a deeper consideration and verification of the NMR approach, which is based on using model compounds to provide the NMR signal pattern of individual tautomers.

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“…S2 and S3 in the ESI). The phase analysis revealed that Sudan I consists of 82% of the polymorph I (Oliveri et al 1989), 8% of the polymorph II (Liu et al 1997), and 10% of the polymorph III (Ferreira et al 2013), whereas 4-methylumbelliferone exists in the anhydrous form (Panini et al 2014). …”

Section: Powder X-ray Diffractionmentioning

confidence: 99%

“…The resulted diffractograms are presented in Figs (Oliveri et al 1989), the 4-MU hydrate (Panini et al 2014), and Na 2 CO 3 ·NaHCO 3 ·2H 2 O (Candlin 1956) (see Fig. 3), whereas the base-free crystallization indicates the coexistence of crystalline forms of Sudan I, polymorph I (Oliveri et al 1989), Sudan I, polymorph II (Liu et al 1997), and 4-methylumbelliferone (Panini et al 2014). The simulated bands for Sudan I polymorph II are somewhat shifted due to temperature effect (Liu et al 1997).…”

Section: Solid-state Investigationsmentioning

confidence: 99%

“…3), whereas the base-free crystallization indicates the coexistence of crystalline forms of Sudan I, polymorph I (Oliveri et al 1989), Sudan I, polymorph II (Liu et al 1997), and 4-methylumbelliferone (Panini et al 2014). The simulated bands for Sudan I polymorph II are somewhat shifted due to temperature effect (Liu et al 1997). Unfortunately, none of these patterns could be attributed to a phase where direct interactions of 4-MU and Sudan I at molecular scale are observed.…”

Section: Solid-state Investigationsmentioning

confidence: 99%

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Improving Fluorometric Determination of Water Content in Aprotic Solvents

et al. 2017

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A fluorometric method allowing quantification of minute amounts of water in highly lipophilic solvents is proposed. This approach takes advantage of resonance energy transfer between 4-methylumbelliferone and Sudan I. The conditions required to observe effective energy transfer have been elucidated. The emission band of the donor molecule (4-methylumbelliferone) depends strongly on the water content-its position is affected by protolytic reactions occurring between the fluorescent dye and water in lipophilic solvent media. In consequence, the extent of overlap between the emission band of the donor and absorption peak of the acceptor scales with the water concentration. The sensitivity of this optical system can be considerably increased by addition of organic bases. The dependence of the emission band of 4-methylumbelliferone/Sudan I system on minute amount of water present in lipophilic solutions opens up possibility of determination of water content in these media at the unique wavelength, in a turn on mode. The presented system was successfully applied to determine water in model commercial oil samples. It was shown that using herein proposed method the increase of water contents in the sample can be observed as increase of the emission intensity, despite the native fluorescence of the vegetable oil samples. For these samples, a good correlation with golden standard Karl Fischer titration was obtained.

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Effect of an Electric Field on the Growth and Optoelectronic Properties of Quasi-One-Dimensional Organic Single Crystals of 1-(Phenylazo)-2-naphthol

Cited by 32 publications

References 23 publications

Addressing of Optoelectronic Memory of Thin Film Zinc Porphyrin with Crossed 5 μm Indium Tin Oxide Arrays

Addressing of Optoelectronic Memory of Thin Film Zinc Porphyrin with Crossed 5 μm Indium Tin Oxide Arrays

4-Carboxyl-2,6-dinitrophenylazohydroxynaphthalenes tautomerism NMR re-explained and other methods verified

Improving Fluorometric Determination of Water Content in Aprotic Solvents

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