Abstract:A novel molecular device (trans-azobenzene embedded N-(11-pyrenyl methyl)aza-21-crown-7) with double functional devices was designed on the basis of theoretical calculations. Pyrenyl methyl covalently bonded to aza-21crown-7 at the nitrogen position interacting with a series of alkaline-earth metal cations (Mg 2+ , Ca 2+ , Sr 2+ , and Ba 2+ ) was investigated. The fully optimized geometries and real frequency calculations were investigated using a computational strategy based on density functional theory at B3… Show more
“…Computational methods were also used by Wang and co-workers [ 145 ] to study trans -azobenzene embedded N -(11-pyrenyl methyl)aza-21-crown-7 27 (Fig. 18 ) as a fluorogenic receptor for alkaline-earth metal cations.…”
Section: Crown Ethers With Azobenzene Moiety(-ies)mentioning
confidence: 99%
“… Fig. 18 Azobenzene embedded N -(11-pyrenyl methyl)aza-21-crown-7, 27 studied by DFT by Wang and co-workers [ 145 ] …”
Section: Crown Ethers With Azobenzene Moiety(-ies)mentioning
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.
“…Computational methods were also used by Wang and co-workers [ 145 ] to study trans -azobenzene embedded N -(11-pyrenyl methyl)aza-21-crown-7 27 (Fig. 18 ) as a fluorogenic receptor for alkaline-earth metal cations.…”
Section: Crown Ethers With Azobenzene Moiety(-ies)mentioning
confidence: 99%
“… Fig. 18 Azobenzene embedded N -(11-pyrenyl methyl)aza-21-crown-7, 27 studied by DFT by Wang and co-workers [ 145 ] …”
Section: Crown Ethers With Azobenzene Moiety(-ies)mentioning
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.
“…Among the photoresponsive units, azobenzene, an easily available and well-known photochromic molecule, rapidly and reversibly switches the E / Z isomer under exposure to UV or visible light, resulting in significant changes in its dipole moment and conformation . Azo-crown ether, consisting of azobenzenes and crown ethers, is one of the most important photoswitchable supramolecules. Shinkai et al developed various elegant azo-crown ethers such as the butterfly crown ether and macrocycle units containing azobenzene and crown ether, which can switch their geometry, extraction, and coordination ability with alkali metals through the photoisomerization of azobenzene units (Figure A).…”
Azo-crown ether-based photoswitching chiral phase transfer catalysts have been developed to control the catalytic activity by photoirradiation. Azobenzene binaphthyl crown ether (ABCE) can switch its reactivity and selectivity through structural transformation of the crown ether moiety induced by E/Z photoisomerization of azobenzene. (Z)-ABCE promoted enantioselective alkylation of the glycine Schiff base to afford chiral amino acid derivatives in good yields with high enantiomer ratios. In contrast, (E)-ABCE hindered the reaction progress under the same conditions.
This study presents recent advances in photoswitchable chiral organocatalysts and their applications in the photomodulation of enantioselective reactions. Under irradiation with an appropriate wavelength of light, the E/Z‐photoisomerization of the photoresponsive units on the catalysts leads to the control of the catalytic activity and/or selectivity of the enantioselective reactions. Additionally, this study elucidates the design, synthesis, and catalytic application of the fabricated azobenzene BINOL‐based photoswitchable chiral phase‐transfer catalysts. This account will provide insights into the appropriate design of a photoswitchable chiral organocatalyst that can achieve both good enantioselectivity and photocontrol.
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