Stability and partial oligomerization of naphthalene under high pressure at room temperature

Shinozaki, Ayako; Mimura, Koichi; Nishida, Tamihito; Inoue, Toru; Nakano, Satoshi; Kagi, Hiroyuki

doi:10.1016/j.cplett.2016.09.042

Cited by 17 publications

(11 citation statements)

References 38 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…One-dimensional sp 3 carbon nanothreads form by the slow, room-temperature compression and decompression of benzene or other small aromatics , (unlike the amorphous products recovered from more rapid applications of pressure , ). Their structural organization with a diamond-like tetrahedral core foreshadows the promise of novel mechanical, thermal, and optical properties. − A nanothread lives at the juncture between crystalline rigidity and polymeric flexibility: its subnanometer width and rigid carbon–carbon cage structure make it one of the narrowest objects capable of sustaining translational and orientational order along its axis.…”

mentioning

confidence: 99%

“…As samples were slowly compressed to 35 GPa over 10–12 h, the liquid froze at ∼0.4 GPa, as expected. , Near 7 GPa, samples start taking on a yellow-orange hue, transforming to brown-amber upon approaching the final pressure of ∼35 GPa (Figure a). Such a color change can only occur when molecules are close to each other (less than ∼3 Å) and indicates a reduction of optical gap. The color change was irreversible upon decompression, providing evidence of a chemical reaction. , Before discussing this reaction product, we briefly describe the behavior of crystalline molecular thiophene prior to polymerization.…”

mentioning

confidence: 99%

See 1 more Smart Citation

Evidence for Orientational Order in Nanothreads Derived from Thiophene

Biswas

Ward

Wang

et al. 2019

J. Phys. Chem. Lett.

View full text Add to dashboard Cite

Nanothreads are one-dimensional sp 3 hydrocarbons that pack within pseudohexagonal crystalline lattices. They are believed to lack long-range order along the thread axis and also lack interthread registry. Here we investigate the phase behavior of thiophene up to 35 GPa and establish a pressure-induced phase transition sequence that mirrors previous observations in low-temperature studies. Slow compression to 35 GPa results in the formation of a recoverable saturated product with a 2D monoclinic diffraction pattern along (0001) that agrees closely with atomistic simulations for single crystals of thiophene-derived nanothreads. Paradoxically, this lower-symmetry packing signals a higher degree of structural order since it must arise from constituents with a consistent azimuthal orientation about their shared axis. The simplicity of thiophene reaction pathways (with only four carbon atoms per ring) apparently yields the first nanothreads with orientational order, a striking outcome considering that a single point defect in a 1D system can disrupt long-range structural order.

show abstract

mentioning

confidence: 99%

mentioning

confidence: 99%

Evidence for Orientational Order in Nanothreads Derived from Thiophene

Biswas

Ward

Wang

et al. 2019

J. Phys. Chem. Lett.

View full text Add to dashboard Cite

show abstract

“…capillary column, with a 0.25 μm layer of HP-5 (Agilent Technology Co.). The GC column temperature was programmed as in our previous studies 12,13 . A GC-flame ionization detector (GC/FID, GC-2014; Shimadzu) equipped with an HP-5 capillary column was used for quantitative analysis of the residual 2,3-naphthyridine and reaction products.…”

Section: Methodsmentioning

confidence: 99%

“…Pressure-induced irreversible chemical reactions with amorphization of solid benzene and polycyclic aromatic hydrocarbons (PAHs) at room temperature have been reported 7–14 . Neighboring molecules in the solid crystal converge with increasing pressure and finally exceed an irreversible reaction threshold to form dimers and trimers 11–13,15 . In addition, a novel nanocarbon material called “carbon nanothread” was formed after the slow compression and decompression of benzene up to 20 GPa and exhibited a one-dimensional structure with sp 3 bonding 16–18 .…”

Section: Introductionmentioning

confidence: 99%

Decomposition and oligomerization of 2,3-naphthyridine under high-pressure and high-temperature conditions

Shinozaki

Mimura

Nishida

2019

Sci Rep

Self Cite

View full text Add to dashboard Cite

The chemical reaction of 2,3-naphthyridine, a nitrogen-containing aromatic compound, was investigated at pressures ranging from 0.5 to 1.5 GPa and temperatures from 473 to 573 K. A distinct decrease in the amount of residual 2,3-naphthyridine was observed in the samples recovered after reaction at ˃523 K at 0.5 and 1.0 GPa, and ˃548 K at 1.5 GPa. The formation of o -xylene and o -tolunitrile accompanied a decreasing N/C ratio of the reaction products, indicating decomposition of the aromatic ring and release of nitrogen. Precise analysis of the reaction products indicated the oligomerization of decomposed products with the residual 2,3-naphthyridine to form larger molecules up to 7mers. Nitrogen in the aromatic ring accelerated reactions to decompose the molecule and to oligomerize at lower temperatures than those typically reported for aromatic hydrocarbon oligomerization. The major reaction mechanism was similar between 0.5 and 1.5 GPa, although larger products preferentially formed in the samples at higher pressure.

show abstract

“…Pressure has a significant effect on the structure and properties of PAHs [8][9][10][11]. For example, naphthalene is partially oligomerized above 15 GPa at room temperature, and this can be promoted by reducing intermolecular distance with the action of pressure [12]; pressure can effectively reduce the bandgap of oligoacenes, which would affect their electron transport performance [13].…”

Section: Introductionmentioning

confidence: 99%

Improved Dielectric Properties and Grain Boundary Effect of Phenanthrene Under High Pressure

et al. 2021

View full text Add to dashboard Cite

In situ impedance measurements, Raman measurements and theoretical calculations were performed to investigate the electrical transport and vibrational properties of polycrystalline phenanthrene. Two phase transitions were observed in the Raman spectra at 2.3 and 5.9 GPa, while phenanthrene transformed into an amorphous phase above 12.1 GPa. Three discontinuous changes in bulk and grain boundary resistance and relaxation frequency with pressure were attributed to the structural phase transitions. Grain boundaries were found to play a dominant role in the carrier transport process of phenanthrene. The dielectric performance of phenanthrene was effectively improved by pressure. A significant mismatch between Z″ and M″ peaks was observed, which was attributed to the localized electronic conduction in phenanthrene. Theoretical calculations showed that the intramolecular interactions were enhanced under compression. This study offers new insight into the electrical properties as well as grain boundary effect in organic semiconductors at high pressure.

show abstract

Stability and partial oligomerization of naphthalene under high pressure at room temperature

Cited by 17 publications

References 38 publications

Evidence for Orientational Order in Nanothreads Derived from Thiophene

Evidence for Orientational Order in Nanothreads Derived from Thiophene

Decomposition and oligomerization of 2,3-naphthyridine under high-pressure and high-temperature conditions

Improved Dielectric Properties and Grain Boundary Effect of Phenanthrene Under High Pressure

Contact Info

Product

Resources

About