Zur Kenntnis des Kohlenstoffringes. 49. Mitteilung. Vielgliedrige Cyclanole und Cyclanol‐acetate

Kobelt, Margrit; Barman, Pranjit; Prelog, V.; Růžička, L.

doi:10.1002/hlca.19490320136

Cited by 44 publications

(8 citation statements)

References 12 publications

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“…Interestingly, the odd–even effect has been previously observed for cyclic alkanes and their derivatives, and it has manifested itself in many properties such as melting points, heats of fusion, refraction, and even 1 H and 13 C NMR chemical shifts . It has been explained in terms of how well molecules can pack with one another depending on the most thermodynamically stable ring conformation.…”

Section: Resultsmentioning

confidence: 94%

Influence of the Carboxylic Acid Additive Structure on the Properties of Poly(3-hexylthiophene) Prepared via Direct Arylation Polymerization (DArP)

2015

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Carboxylic acids are known to have a profound effect on the rate of direct arylation. Despite this, little attention has been paid to them as additives for direct arylation polymerization (DArP). Here we report the influence of the carboxylic acid chemical structure on the properties of poly(3-hexylthiophene) (P3HT) prepared via DArP. We study the effect that acid pK a, steric bulk, and backbone cyclization have on the reactivity of the DArP catalytic system. We found that pK a values do not correlate with DArP reactivity in the pK a range of 4.76–5.05. The increase of acid size in the classes of linear, secondary, and tertiary acids leads to a continuous increase in polymer yield and molecular weight, whereas for the case of cyclic secondary acids the trend is reversed and a decrease of acid size leads to an increase in polymer yield and molecular weight in an alternating (zigzag) fashion depending on whether the acid contains an even or odd number of carbons. A profound enhancement of reactivity was found for the case of the smallest cyclopropanecarboxylic acid, which yields P3HT with remarkably high molecular weights (M n 33.4 kDa and M w 207.1 kDa), which is expected to benefit the development of direct arylation protocols for inherently less reactive substrates.

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Section: Resultsmentioning

confidence: 94%

Influence of the Carboxylic Acid Additive Structure on the Properties of Poly(3-hexylthiophene) Prepared via Direct Arylation Polymerization (DArP)

2015

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“…The values of the permittivity ε ∞ , necessary for use of eq , were estimated by a simple method on the basis of the literature data on the refraction index (Merck data) and the density of cyclooctanone. , The value of the dipole moment of single cyclooctanone molecules were taken as μ 1 = 2.9 D…”

Section: Resultsmentioning

confidence: 99%

Phase Transition from Liquid to Disordered Solid Phase of Cyclooctanone Studied with Dielectric Methods

Świergiel

Jadżyn

2012

J. Phys. Chem. B

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The dielectric studies performed for cyclooctanone in its static dielectric regime have shown that at the phase transition from liquid to disordered (plastic) solid phase of the compound, the following singular phenomena occur: (a) the static permittivity (ε(s)) exhibits a small increase at the transition, instead of that usually observed for polar liquids, a strong decrease of the permittivity at the transition to the crystalline solid phase; (b) temperature dependence of the permittivity, ε(s)(T), is practically the same in both phases, reflecting the same dipolar orientational entropy increment induced by the probing electric field; (c) a distinct jump occurs in the slope of the frequency dependence (in log-log scale) of the dielectric losses due to an ionic current, from the "ohmic" value -1 in the liquid phase to about -0.9 just after the transition to the plastic phase; (d) a similar jump is observed in the shape of the electric modulus spectra of cyclooctanone. The results clearly show the liquid-like freedom in the molecular dynamics in the plastic phase as well as similar intermolecular interactions in both phases of cyclooctanone. The differences in the dielectric losses frequency behavior may reflect the change in the ions dynamics: from the normal translational Brownian diffusion in the liquid phase to the subdiffusional dynamics in the plastic phase.

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“…Preparation of Starting Materials. Dodecyl acetate (4),9 cyclododecyl acetate (7),10 1 -methylcyclohexyl acetate (10),11 and 1adamantyl acetate (17a)12 were preparéd by standard procedures.…”

Section: Methodsmentioning

confidence: 99%

Reductive deoxygenation of esters with trichlorosilane

Baldwin¹,

Haut²

1975

J. Org. Chem.

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Zur Kenntnis des Kohlenstoffringes. 49. Mitteilung. Vielgliedrige Cyclanole und Cyclanol‐acetate

Cited by 44 publications

References 12 publications

Influence of the Carboxylic Acid Additive Structure on the Properties of Poly(3-hexylthiophene) Prepared via Direct Arylation Polymerization (DArP)

Influence of the Carboxylic Acid Additive Structure on the Properties of Poly(3-hexylthiophene) Prepared via Direct Arylation Polymerization (DArP)

Phase Transition from Liquid to Disordered Solid Phase of Cyclooctanone Studied with Dielectric Methods

Reductive deoxygenation of esters with trichlorosilane

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