Comparative study of azobenzene and stilbene bridged crown ether p-tert-butylcalix[4]arene

Rojanathanes, Rojrit; Pipoosananakaton, Bongkot; Tuntulani, Thawatchai; Bhanthumnavin, Worawan; Orton, James B.; Cole, S.; Hursthouse, Michael B.; Grossel, Martin C.; Sukwattanasinitt, Mongkol

doi:10.1016/j.tet.2004.11.020

Cited by 20 publications

(8 citation statements)

References 24 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The complete synthesis path is described in Scheme 1 . Calix 1 is proposed to form complexes with Na + and K + [ 56 ]. For the introduction of proton-ionizable groups to improve the complexation behavior, the two remaining free OH groups were modified by alkylation with ethyl bromoacetate to yield calix 2 .…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Ionizable Calix[4]arenes for Chelation of Selected Divalent Cations

et al. 2022

View full text Add to dashboard Cite

Two sets of functionalised calix[4]arenes, either with a 1,3-crown ether bridge or with an open-chain oligo ether moiety in 1,3-position were prepared and further equipped with additional deprotonisable sulfonamide groups to establish chelating systems for selected cations Sr2+, Ba2+, and Pb2+ ions. To improve the complexation behaviour towards these cations, calix[4]arenes with oligo ether groups and modified crowns of different sizes were synthesized. Association constants were determined by UV/Vis titration in acetonitrile using the respective perchlorate salts and logK values between 3.2 and 8.0 were obtained. These findings were supported by the calculation of the binding energies exemplarily for selected complexes with Ba2+.

show abstract

Section: Resultsmentioning

confidence: 99%

Synthesis of Ionizable Calix[4]arenes for Chelation of Selected Divalent Cations

et al. 2022

View full text Add to dashboard Cite

show abstract

“…Trans/cis isomerization in biology can be used to transport ions across membranes if the conformationally versatile molecule permits a reversible and controllable binding of the cations, and if the chromophore can undergo reversible photoreactions. − With respect to antibiotic ion carriers, it is of utmost importance to take into account the membrane phase and the ease of the isomerization process in these environments, since steric hindrances and interactions with charged groups at the edges of the membrane depend on the conformation of the molecule. For biological systems, the azobenzene chromophore has an extra feature as its fluorescence anisotropy depends on the medium, which is found to affect the overall rotation and internal motions of the excited molecular probe. , Recently, we proved that the location and orientation of a cis azobenzene derivative in a liquid disordered membrane phase profoundly differs from the ones in a solid gel phase.…”

Section: Introductionmentioning

confidence: 99%

Push/Pull Effect as Driving Force for Different Optical Responses of Azobenzene in a Biological Environment

Knippenberg

Osella

2020

J. Phys. Chem. C

View full text Add to dashboard Cite

The specific relationship between the alkyl tail lengths of four azobenzene probes embedded in DOPC liquid disorder membrane and their (non) linear optical (NLO) properties have been considered in the current study. Using extensive molecular dynamics calculations, the push/pull effect of the alkyl tails on the position and orientation of the probes in the model membrane are discussed. The simulations indicate that with increasing tail lengths the cis isomers are pushed closer to the membrane surface, while the trans ones are rather pulled toward the membrane center. Throughout hybrid quantum mechanics/molecular mechanics calculations, the linear and nonlinear optical properties of these compounds have been investigated. The pushing effect of the tails for cis azobenzene is translated in strong responses in the (non) linear optical spectroscopies, while the opposite is seen for the trans isomers. The cis isomer can be seen as the active state of the azobenzene compound for membrane recognition. The current work highlights the correlation between the tails of photosensitive membrane probes and their NLO properties, and focuses on unexpected behaviors of azobenzene derivatives in biological environments which can be exploited in distinguishing between soft and stiff cellular compartments that are of utmost importance for ion carrier transport.

show abstract

“…In some cases, photoresponsive groups have been doped into the polymer network as a guest molecule. A number of chromophores have been examined for both functionalized and guest−host approaches to synthesizing photoresponsive polymeric materials including spyropyranes, azobenzenes, , and stilbenes . Regardless of the approach or chromophore used, approximately 1% photogenerated expansive and contractive strains have been realized in conventional polymeric materials.…”

Section: Introductionmentioning

confidence: 99%

Relationship between the Photomechanical Response and the Thermomechanical Properties of Azobenzene Liquid Crystalline Polymer Networks

et al. 2010

View full text Add to dashboard Cite

We report on the influence of cross-link density of azobenzene-containing liquid crystal polymer networks (azo-LCNs) on the thermomechanical properties and the laser-directed bending of cantilevers consisting of these materials. Cross-link density of azo-LCN was increased by adjusting the length of photocuring from 1 to 120 min. The storage modulus (E 0 ), loss modulus (E 00 ), and glass transition temperature (T g ) of the azo-LCNs increase with cross-link density. Increasing the cross-link density of the polydomain azo-LCN reduces the magnitude of the bending angle of the cantilevers. The relationship between the thermomechanical and photomechanical properties of the polydomain azo-LCN reported here is further elucidated in the examination of laser-directed bending over a wide range of temperature. The temperature dependence of the equilibrium photodriven bending angle is shown to be strongly related to the temperature dependence of the storage modulus for a given azo-LCN sample. Normalizing the temperature dependence of the photomechanical response of the azo-LCN cantilevers by the T g provides a master curve that can be used to tailor the photomechanical response.

show abstract

Comparative study of azobenzene and stilbene bridged crown ether p-tert-butylcalix[4]arene

Cited by 20 publications

References 24 publications

Synthesis of Ionizable Calix[4]arenes for Chelation of Selected Divalent Cations

Synthesis of Ionizable Calix[4]arenes for Chelation of Selected Divalent Cations

Push/Pull Effect as Driving Force for Different Optical Responses of Azobenzene in a Biological Environment

Relationship between the Photomechanical Response and the Thermomechanical Properties of Azobenzene Liquid Crystalline Polymer Networks

Contact Info

Product

Resources

About