Azobenzene derivatives due to their photo- and electroactive properties are an important group of compounds finding applications in diverse fields. Due to the possibility of controlling the trans–cis isomerization, azo-bearing structures are ideal building blocks for development of e.g. nanomaterials, smart polymers, molecular containers, photoswitches, and sensors. Important role play also macrocyclic compounds well known for their interesting binding properties. In this article selected macrocyclic compounds bearing azo group(s) are comprehensively described. Here, the relationship between compounds’ structure and their properties (as e.g. ability to guest complexation, supramolecular structure formation, switching and motion) is reviewed.
The preparation and characterization of products of the chemical and photochemical rearrangements of a 19-membered o,o'-azoxybenzocrown are presented. In photochemical rearrangement, besides the expected product i. e. 19-membered o-hydroxy-o,o'-azobenzocrown (19-o-OH) obtained under defined conditions with 75 % yield, also other macrocyclic products were isolated and identified, namely: 19-membered phydroxy-o,o'-azobenzocrown (19-p-OH), 21-membered o'hydroxy-o,p'-azobenzocrown (21-o'-OH) and 19-membered macrocycle containing a 5-membered ring bearing an aldehyde group (19-al). The structures of two atypical products of the photochemical rearrangement-21-o'-OH and 19-al-were determined in the solid state by X-ray analysis and in solution using NMR spectroscopy. Tautomeric equilibrium of the formed hydroxyazobenzocrowns and its change depending on acidity/ basicity of the environment and alkali and alkaline earth metal cations complexation were studied using UV-Vis spectrophotometry, spectrofluorimetry and 1 H NMR spectroscopy.
Novel biscrowns 1 and 2 were synthesized from 13-membered azobenzocrown ethers containing bromoalkylenoxy chains in para position relative to the azo group. The synthesized diester molecules are dodecylmethylmalonic acid derivatives differing by the linker length. The synthesized compounds have the potential of being used as sodium ionophores in ion-selective electrodes. They were characterized and used as ionophores in classic and miniature, solid contact (screen-printed and glassy carbon) membrane ion-selective electrodes. Compound 3, a similar monoester derivative of 13-membered azobenzocrown, was synthesized and used in membrane electrodes for comparison. Lipophilicity of new ionophores was determined by TLC. Lipophilicity of bis(azobenzocrown)s was found to be within the range of logPTLC = 12–13. It was observed that the particularly important selectivity coefficients logK
Na,K determined for new electrodes, being logK
Na,K = −2.5 and −2.6 (SSM, 0.1 M), are better than those of the electrodes featuring seven out of the nine commercially available sodium ionophores. It was concluded that the ionophore 1 creates, in acetone, with sodium iodide, complex of 1:1 stoichiometry (sandwich complex) with stability constant (logK) ca. 3.0.
Depleting fossil fuel resources and anthropogenic climate changes are the reasons for the intensive development of new, sustainable technologies based on renewable energy sources. One of the most promising strategies is the utilization of hydrogen as an energy vector. However, the limiting issue for large-scale commercialization of hydrogen technologies is a safe, efficient, and economical method of gas storage. In industrial practice, hydrogen compression and liquefaction are currently applied; however, due to the required high pressure (30–70 MPa) and low temperature (−253 °C), both these methods are intensively energy consuming. Chemical hydrogen storage is a promising alternative as it offers safe storage of hydrogen-rich compounds under ambient conditions. Although many compounds serving as hydrogen carriers are considered, some of them do not have realistic perspectives for large-scale commercialization. In this review, the three most technologically advanced hydrogen carriers—dimethyl ether, methanol, and dibenzyltoluene—are discussed and compared. Their potential for industrial application in relation to the energy storage, transport, and mobility sectors is analyzed, taking into account technological and environmental aspects.
Hydrogen-based technologies are among the most promising solutions to fulfill the zero-emission scenario and ensure the energy independence of many countries. Hydrogen is considered a green energy carrier, which can be utilized in the energy, transport, and chemical sectors. However, efficient and safe large-scale hydrogen storage is still challenging. The most frequently used hydrogen storage solutions in industry, i.e., compression and liquefaction, are highly energy-consuming. Underground hydrogen storage is considered the most economical and safe option for large-scale utilization at various time scales. Among underground geological formations, salt caverns are the most promising for hydrogen storage, due to their suitable physicochemical and mechanical properties that ensure safe and efficient storage even at high pressures. In this paper, recent advances in underground storage with a particular emphasis on salt cavern utilization in Europe are presented. The initial experience in hydrogen storage in underground reservoirs was discussed, and the potential for worldwide commercialization of this technology was analyzed. In Poland, salt deposits from the north-west and central regions (e.g., Rogóźno, Damasławek, Łeba) are considered possible formations for hydrogen storage. The Gubin area is also promising, where 25 salt caverns with a total capacity of 1600 million Nm3 can be constructed.
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