Electron transfer properties of non-alternant, substituted compounds related to fluoranthene. Experimental determination and theoretical modeling of electrochemical oxidation and reduction potentials in non-aqueous solution

Steffen, L. Kraig; Plummer, Benjamin F.; Braley, Tala L.; Reese, W. Greg; Zych, Kathryn; Dyke, Gregory Van; Gill, Michael

doi:10.1002/(sici)1099-1395(199708)10:8<623::aid-poc929>3.0.co;2-c

Cited by 7 publications

(3 citation statements)

References 22 publications

(19 reference statements)

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“…7a–d,7h–k,9 The study of these CPHs has resulted not only in functional materials, but also provided insight into fundamental chemical principles, such as the nature of the carbon-carbon bond, singlet-biradical character, and aromaticity and antiaromaticity, knowledge that in turn can be applied to designing better performing materials. 7a–d,7h–k,9a,9e,9f,10 …”

Section: Introductionmentioning

confidence: 99%

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Indacenodibenzothiophenes: synthesis, optoelectronic properties and materials applications of molecules with strong antiaromatic character

et al. 2016

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Indeno[1,2-b]fluorenes (IFs), while containing 4n π-electrons, are best described as two aromatic benzene rings fused to a weakly paratropic s-indacene core. In this study, we find that replacement of the outer benzene rings of an IF with benzothiophenes allows the antiaromaticity of the central s-indacene to strongly reassert itself. Herein we report a combined synthetic, computational, structural, and materials study of anti- and syn-indacenodibenzothiophenes (IDBTs). We have developed an efficient and scalable synthesis for preparation of a series of aryl- and ethynyl-substituted IDBTs. NICS-XY scans and ACID calculations reveal an increasingly antiaromatic core from [1,2-b]IF to anti-IDBT, with syn-IDBT being nearly as antiaromatic as the parent s-indacene. As an initial evaluation, the intermolecular electronic couplings and electronic band structure of a diethynyl anti-IDBT derivative reveal the potential for hole and / or electron transport. OFETs constructed using this molecule show the highest hole mobilities yet achieved for a fully conjugated IF derivative.

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Section: Introductionmentioning

confidence: 99%

“…Since 2010, our group 14 and others 10g,10i,13b,15 have investigated compounds based on the indenofluorene (IF) scaffold (IFs 1–7 Fig. 1).…”

Section: Introductionmentioning

confidence: 99%

Indacenodibenzothiophenes: synthesis, optoelectronic properties and materials applications of molecules with strong antiaromatic character

et al. 2016

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“…The molecule used in the QSAR analysis were set up with molecular builder and the geometry was firstly optimized with molecular dynamics, then molecular mechanics using the CVFF force field, and finally fully optimized by energy minimization using the PM3 Hamiltonian contained in the molecular package MOPAC ver.2000. The conductor-like screening model (COSMO) method was used to approximate the effect of solvation effect, which obtains reasonable free energies of solvation [13,14]. The dielectric constant values of water used in the COSMO-PM3 method were taken from Haar et al [15].…”

Section: Introductionmentioning

confidence: 99%

Calculation of Aqueous Solubility of Organic Compounds from Molecular Structural Properties

Tomida¹,

Nishino²,

Yokoyama³

2007

Jpn. J. Thermophys. Prop.

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The quantitative structure-activity relationships (QSAR) correlations were developed for the aqueous solubility of organic compounds at 298.15, 473.15, and 573.15 K. To elucidate the molecular structural variables to control the solvation phenomena, we firstly developed the QSAR correlation of solubility of 108 organic molecules in water at 298.15 K with the use of experimentally and theoretically derivable variables. The experimental variable used was the octanol-water partition coefficient and melting point, while the theoretical variables were LUMO energy and total molecular surface area, which were determined with the COSMO-PM3 method. Based on the results at 298.15 K, the QSAR correlations for aqueous solubility at 473.15 K and 573.15 K were determined with the use of the literature solubility data for 21 compounds at these two high temperatures. It was found that the QSAR correlation with COSMO-PM3 method is able to predict the aqueous solubility of organic compounds at 473.15 and 573.15 K from the molecular structural properties and the melting temperature, since the octanol-water partition coefficient can be predicted from atom/fragment contribution method.

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Higher, Stronger, Better…︁ A Review of 5 Volt Cathode Materials for Advanced Lithium‐Ion Batteries

Kraytsberg

Ein‐Eli

2012

Advanced Energy Materials

654

455

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The ever-increasing demand for high-performing, economical, and safe power storage for portable electronics and electric vehicles stimulates R&D in the fi eld of chemical power sources. In the past two decades, lithium-ion technology has proven itself a most robust technology, which delivers high energy and power capabilities. At the same time, current technology requires that the energy and power capabilities of Li-ion batteries be 'beefed up' beyond the existing state of the art. Increasing the battery voltage is one of the ways to improve battery energy density; in Li-ion cells, the objective of current research is to develop a 5-volt cell, and at the same time to maintain high specifi c charge capacity, excellent cycling, and safety. Since current anode materials possess working potentials fairly close to the potential of a lithium metal, the focus is on the development of cathode materials. This work reviews and analyzes the current state of the art, achievements, and challenges in the fi eld of high-voltage cathode materials for Li-ion cells. Some suggestions regarding possible approaches for future development in the fi eld are also presented. REVIEW compromised). Since the carbonaceous anode potential (vs. Li/Li + ) V anode Li Li + ∼ 0, the cell potential, V cell , is dictated by the cathode potential V cathode Li Li + , i.e., by the type of cathode material employed. Electrolyte RequirementsCell potential, V cell is not governed by cell electrolyte, but the employment of inadequate electrolyte compromises cell performance: the electrolyte should not experience oxidation/ reduction at the electrode surface in the course of operation. If the electrolyte solution comprises solvent, S, and ion species S{A + }{B} − , the thermodynamic conditions of electrolyte stability are that the potentials of the electrolyte redox reactions should be in the cell voltage window, as shown in Figure 2 . The necessary conditions for these potentials are given by Equation 2 : the Li-ion material cost and their environmental compatibility now receive much attention.

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Electron transfer properties of non-alternant, substituted compounds related to fluoranthene. Experimental determination and theoretical modeling of electrochemical oxidation and reduction potentials in non-aqueous solution

Cited by 7 publications

References 22 publications

Indacenodibenzothiophenes: synthesis, optoelectronic properties and materials applications of molecules with strong antiaromatic character

Indacenodibenzothiophenes: synthesis, optoelectronic properties and materials applications of molecules with strong antiaromatic character

Calculation of Aqueous Solubility of Organic Compounds from Molecular Structural Properties

Higher, Stronger, Better…︁ A Review of 5 Volt Cathode Materials for Advanced Lithium‐Ion Batteries

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