Isolation and properties of hydrocarbon salts

Okamoto, Kunio; Kitagawa, Toshikazu; Takeuchi, Ken′ichi; Komatsu, Kôichi; Kinoshita, Tomomi; Aonuma, Shuji; Nagai, Masao; Miyabo, Atsushi

doi:10.1021/jo00290a034

Cited by 42 publications

(26 citation statements)

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“…4.4b(iii)) [17a]. Furthermore, similar gelation processes were observed in Fmoc-protected amino acid 7c and the mixture of 7b and 7c in the presence of Na 2 CO 3 using an enzymatic reaction that dephosphorylated the PO 4 3− of 7c [17b]. Hydrogels can be constructed by the interaction between anions and designed zwitterionic molecules.…”

Section: Anion-driven Formation Of Supramolecular Gelsmentioning

confidence: 81%

“…Hydrogels can be constructed by the interaction between anions and designed zwitterionic molecules. Mocerino and Ogden et al reported proline-functionalized calix [4]arene 8 ( Fig. 4.4c(i)), which exhibited the formation of anion-triggered hydrogels [18].…”

Section: Anion-driven Formation Of Supramolecular Gelsmentioning

confidence: 99%

“…is significantly challenging since these anions may be susceptible to electrophilic attacks due to their excess electrons [4]. One strategy for the efficient formation of planar anions is the complexation of inorganic anions by -conjugated planar anion-responsive molecules, which afford planar anionic species as receptor-anion complexes.…”

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confidence: 99%

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Anion‐Driven Supramolecular Self‐Assembled Materials

Maeda¹

2013

Intelligent Stimuli‐Responsive Materials

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Recently, soft materials have attracted increased attention as transformable functional materials because of their moderate mobilities and flexibilities, which readily enable them to change their bulk shapes and properties depending on the ambient conditions [1]. In particular, soft materials comprising -conjugated molecules exhibit attractive properties and have the potential for use in the fabrication of electronic and optical devices whose properties can be tuned according to the environment. The introduction of building subunits that are responsive to chemical stimuli would result in supramolecular structures that exhibit stimuli-responsive behaviors and result in the formation of various materials comprising multiple components. Therefore, the combination of building units and additives (chemical stimuli) provides a large number of soft materials possessing potential utility for various applications.The arrangement of appropriately designed charged species using electrostatic and other noncovalent interactions such as the van der Waals interaction would provide functional ion-based soft materials. Just as the electrostatic attraction between opposite charges can control the location of ionic species, the electrostatic repulsion between identical charges can determine the state of ion-based assemblies. Focusing on the geometries of charged components composed of ion-based assemblies, -conjugated planar cations and anions are suitable for the formation of stacking assemblies [2]. In contrast to the synthesis of planar cations, some of which are stable enough for various investigations [3], the synthesis of -conjugated planar anions

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Section: Anion-driven Formation Of Supramolecular Gelsmentioning

confidence: 81%

Section: Anion-driven Formation Of Supramolecular Gelsmentioning

confidence: 99%

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Anion‐Driven Supramolecular Self‐Assembled Materials

Maeda¹

2013

Intelligent Stimuli‐Responsive Materials

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“…This seemingly strange behavior may be understood by interpreting it as reflecting some relief of intermolecular steric congestion in the crystal lattice by ionization. 26,27 Free energies of heterolysis, shown in Table 2, indicate that the dissociation is much more favored in DMSO than in sulfolane, in spite of the magnitude of the dielectric constants (46.68 and 43.3, respectively), which are nearly identical with each other. However, the former has a much greater donor number than the latter (29.8 and 14.8, respectively 35 ).…”

Section: Solvent Effectsmentioning

confidence: 95%

“…26 When dissolved in benzene, chloroform or carbon tetrachloride, this salt, a green solid, is completely converted into the covalent form 14-10, giving a brown solution. In acetonitrile, 1,2-dichloroethane, dichloromethane and THF, the ionic and covalent forms co-exist, in equilibrium.…”

Section: Solvent Effectsmentioning

confidence: 99%

Structural dependence of heterolytic bond dissociation energy of carbon–carbon σ bonds in hydrocarbons

Kitagawa

Takeuchi

1998

J. Phys. Org. Chem.

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The coordination of a resonance-stabilized hydrocarbon cation and anion yielded a series of unprecedented hydrocarbons, which are susceptible to thermal heterolytic cleavage of carbon-carbon s bonds in polar media, generating the original ions under reversible conditions. When the component ions were sufficiently stabilized, some ion pairs were even isolated as solids, thus providing the first examples of hydrocarbon salts. The direct observation of the heterolysis by means of spectroscopy permitted reliable thermodynamic treatments of the observed degree of ionic dissociation. Correlation of the free energy of heterolysis with solvent dielectric constants and parameters of ion stabilities such as pK HA , pK R and redox potentials revealed the importance of the thermodynamic stabilities of ions, the degree of solvation and steric congestion in the starting molecule as major controlling factors in the heterolysis.

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2010

Solvents and Solvent Effects in Organic Chemistry

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Isolation and properties of hydrocarbon salts

Cited by 42 publications

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Anion‐Driven Supramolecular Self‐Assembled Materials

Anion‐Driven Supramolecular Self‐Assembled Materials

Structural dependence of heterolytic bond dissociation energy of carbon–carbon σ bonds in hydrocarbons

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