To mechanochemical dimerization of anthracene. Crystalline phenanthrene under high pressure and shear conditions

Politov, A. A.; Чупахин, А. П.; Tapilin, V. M.; Bulgakov, N. N.; Druganov, A. G.

doi:10.1007/s10947-010-0163-3

Cited by 10 publications

(9 citation statements)

References 6 publications

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“…A mixture of glycerine and water (volume 3:2) was used as a hydrostatic liquid. No shear stress was imposed (Politov et al, 2010;Tapilin et al, 2010). The sample in the DAC was aligned on a diffractometer using the gasket-shadow centring procedure (Budzianowski & Katrusiak, 2004).…”

Section: Methodsmentioning

confidence: 99%

The role of free space in photochemical reactions in crystals at high pressure – the case of 9-methylanthracene

Bąkowicz¹,

Turowska‐Tyrk²

2022

Acta Crystallogr Sect B

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The influence of pressure on the course of [4+4] photodimerization in crystals of 9-methylanthracene is presented. The studies were performed at 0.1 and 0.4 GPa. As a result of the reaction at high pressure, crystals of the pure product were obtained, which allowed for monitoring of the reaction until its completion. The initial increase in the unit-cell volume caused by the reaction under ambient conditions was reduced at high pressure due to the decrease in the void volume. Despite the smaller size of the void volume at high pressure, dimer molecules formed during the reaction changed the orientation of the monomer molecules in the crystal structure. The size of the voids above the terminal rings of the monomers correlates with the position of the terminal rings in the dimer. The reaction rate increased at high pressure, indicating that the decrease in the distance between adjacent monomers caused by pressure dominates over the decrease in the void volume. This distance is statistically constant as the reaction progresses, contrary to the reaction at ambient pressure.

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Section: Methodsmentioning

confidence: 99%

The role of free space in photochemical reactions in crystals at high pressure – the case of 9-methylanthracene

Bąkowicz¹,

Turowska‐Tyrk²

2022

Acta Crystallogr Sect B

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“…Where a new product forms, for example in a multi-phase reaction, this can often take the form of exothermic nucleation. Although proving whether a reaction is thermo or mechanochemical can be challenging, a number of clear examples can be given, including the dark dimerization of aromatic compounds at high pressures ( Engelke and Blais, 1994 ; Politov et al, 2010 ; Friedrich et al, 2020 ), the classic examples of the decomposition of metal halides by Carey Lea ( Carey-Lea, 1892 ; Carey-Lea, 1894 ), the decomposition of alkali metal nitrates, bromates, and chlorates, which give different products and follows inverted trends upon heating and mechanical action ( Boldyrev, 1972 ; Boldyrev et al, 1972 ; Urakaev et al, 1977 ; Boldyrev and Heinicke, 1979 ), or oxidation of gold by carbon dioxide ( Thiessen et al, 1970 ). The relations between mechanochemical and thermochemical nature of the reactions can be compared with a situation when light and temperature act on a sample simultaneously.…”

Section: What Is In a Name?mentioning

confidence: 99%

Tribochemistry, Mechanical Alloying, Mechanochemistry: What is in a Name?

Michalchuk

Болдырева²,

Belenguer³

et al. 2021

Front. Chem.

151

108

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Over the decades, the application of mechanical force to influence chemical reactions has been called by various names: mechanochemistry, tribochemistry, mechanical alloying, to name but a few. The evolution of these terms has largely mirrored the understanding of the field. But what is meant by these terms, why have they evolved, and does it really matter how a process is called? Which parameters should be defined to describe unambiguously the experimental conditions such that others can reproduce the results, or to allow a meaningful comparison between processes explored under different conditions? Can the information on the process be encoded in a clear, concise, and self-explanatory way? We address these questions in this Opinion contribution, which we hope will spark timely and constructive discussion across the international mechanochemical community.

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“…It is familiar that anthracene has the ability to dimerize with photoirradiation. , In the present case, however, it can be ruled out because the photodimerization requires UV light at 365 nm. It is possible that the origin of dimerization is the compressive strain energy accumulated in the anthracene monolayer of Ant-C11-SAM, given that there have been reports on the mechanochemical dimerization of anthracene under very high pressure. − As described above, the lattice constant of the rectangular phase in Ant-C11-SAM is ∼13% smaller than that of the bulk anthracene crystal in ambient conditions and corresponds to the bulk ones under high pressure, i.e., above 5 GPa . A highly compressed anthracene monolayer was achieved in the Ant-C11-SAM because the alkanethiolate moiety prefers the (√3 × √3)R30° superstructure on Au(111) and has a packing density of 0.215 nm 2 /molecule.…”

Section: Resultsmentioning

confidence: 96%

Formation of Highly Ordered Semiconducting Anthracene Monolayer Rigidly Connected to Insulating Alkanethiolate Thin Film

et al. 2018

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The formation and molecular structure of a self-assembled monolayer (SAM) of anthracene-substituted alkanethiol on Au(111) have been investigated by scanning tunneling microscopy and infrared reflection absorption spectroscopy. A clean and well-ordered SAM composed of densely packed "standing-up" molecules is formed by a wetchemical process in air, followed by thermal annealing in vacuum. In the SAM, anthracene moieties are arranged in a bulklike in-plane herringbone structure and keep their crystalline ordering above room temperature, which is in contrast to the less ordering in Au nanoclusters ligated by the anthracene-alkanethiolates. In addition, hexagonal arrangement of anthracene dimer is found on the surface of the SAM. These structures remain after annealing at 400 K. Scanning tunneling spectroscopy performed on the surface shows an energy gap of ∼3.6 eV, similar to the band gap of bulk anthracene. The above results demonstrate that the highly ordered semiconducting anthracene monolayer is successfully formed on the insulating alkanethiolate thin film and has high thermal stability due to a strong chemical bonding across the interface.

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To mechanochemical dimerization of anthracene. Crystalline phenanthrene under high pressure and shear conditions

Cited by 10 publications

References 6 publications

The role of free space in photochemical reactions in crystals at high pressure – the case of 9-methylanthracene

The role of free space in photochemical reactions in crystals at high pressure – the case of 9-methylanthracene

Tribochemistry, Mechanical Alloying, Mechanochemistry: What is in a Name?

Formation of Highly Ordered Semiconducting Anthracene Monolayer Rigidly Connected to Insulating Alkanethiolate Thin Film

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