Anion-tunable control of thermal Z→E isomerisation in basic azobenzene receptors

Dąbrowa, Kajetan; Niedbała, Patryk; Jurczak, Janusz

doi:10.1039/c4cc07798a

Cited by 55 publications

(55 citation statements)

References 41 publications

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“…The electronic effects would seem to be the dominant factor for all guests except Succ = . The suggestion that electron density donation from the bound anions to the azobenzene unit of cis ‐ 2 could be responsible for the observed enhanced rate of cis / trans isomerizations is consistent with a recent study on the effects of anion binding in azobenzene derivatives containing urea units 30. Further studies are in progress in our laboratory, including molecular modeling and variable temperature experiments, to verify the way in which the different bis‐anions affect the isomerization kinetics of the azobenzene unit of receptor 2 .…”

Section: Methodssupporting

confidence: 89%

Host–Guest Chemistry of a Bis‐Calix[4]pyrrole Derivative Containing a trans/cis‐Switchable Azobenzene Unit with Several Aliphatic Bis‐Carboxylates

Cafeo

Kohnke

Mezzatesta

et al. 2015

Chemistry A European J

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The azobenzene unit used as a photochemically and thermally switchable linker in the assembly of a bis-calix[4]pyrrole receptor provides a means to modulate the binding of bis-carboxylates of significant biological importance in cancer research. Conversely, the complexation of different bis-anionic guests has significant kinetic effects on both the photochemical and thermal trans/cis isomerization of the azobenzene unit.

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Section: Methodssupporting

confidence: 89%

Host–Guest Chemistry of a Bis‐Calix[4]pyrrole Derivative Containing a trans/cis‐Switchable Azobenzene Unit with Several Aliphatic Bis‐Carboxylates

Cafeo

Kohnke

Mezzatesta

et al. 2015

Chemistry A European J

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“…In 2014 the group of Jurczak reported the synthesis of receptor 15 (Figure ), featuring an azobenzene moiety bearing either one ( 15 a ) or two ( 15 b ) urea recognition sites in the para position . Building on the idea for which it would be desirable to trigger the switching using a different stimulus than light and heat, in this work, the scientists focused their studies on gaining kinetic control of the thermal Z → E isomerization through the use of chemical triggers.…”

Section: Configurational Selection Following Anion Complexationmentioning

confidence: 99%

Configurational Selection in Azobenzene‐Based Supramolecular Systems Through Dual‐Stimuli Processes

Tecilla

Bonifazi

2020

ChemistryOpen

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Azobenzene is one of the most studied light-controlled molecular switches and it has been incorporated in a large variety of supramolecular systems to control their structural and functional properties. Given the peculiar isomeric distribution at the photoexcited state (PSS), azobenzene derivatives have been used as photoactive framework to build metastable supramolecular systems that are out of the thermodynamic equilibrium. This could be achieved exploiting the peculiar E/Z photoisomerization process that can lead to isomeric ratios that are unreachable in thermal equilibrium conditions. The challenge in the field is to find molecular architectures that, under given external circumstances, lead to a given isomeric ratio in a reversible and predictable manner, ensuring an ultimate control of the configurational distribution and system composition. By reviewing early and recent works in the field, this review aims at describing photoswitchable systems that, containing an azobenzene dye, display a controlled configurational equilibrium by means of a molecular recognition event. Specifically, examples include programmed photoactive molecular architectures binding cations, anions and H-bonded neutral guests. In these systems the non-covalent molecular recognition adds onto the thermal and light stimuli, equipping the supramolecular architecture with an additional external trigger to select the desired configuration composition.[a] Prof. P. Tecilla

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“…The cis – trans isomerization reaction is one of the most studied reactions with regard to chemical control and chemical switching, for example by light8 or mechanical force 9. Very recently it has been shown that the cis – trans isomerization rate can be tuned by the presence of a nearby anion 10…”

mentioning

confidence: 99%

Barrierless Single‐Electron‐Induced cis–trans Isomerization

Klaiman

Cederbaum

2015

Angew Chem Int Ed

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Lowering the activation energy of a chemical reaction is an essential part in controlling chemical reactions. By attaching a single electron, a barrierless path for the cis-trans isomerization of maleonitrile on the anionic surface is formed. The anionic activation can be applied in both reaction directions, yielding the desired isomer. We identify the microscopic mechanism that leads to the formation of the barrierless route for the electron-induced isomerization. The generalization to other chemical reactions is discussed.

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Anion-tunable control of thermal Z→E isomerisation in basic azobenzene receptors

Cited by 55 publications

References 41 publications

Host–Guest Chemistry of a Bis‐Calix[4]pyrrole Derivative Containing a trans/cis‐Switchable Azobenzene Unit with Several Aliphatic Bis‐Carboxylates

Host–Guest Chemistry of a Bis‐Calix[4]pyrrole Derivative Containing a trans/cis‐Switchable Azobenzene Unit with Several Aliphatic Bis‐Carboxylates

Configurational Selection in Azobenzene‐Based Supramolecular Systems Through Dual‐Stimuli Processes

Barrierless Single‐Electron‐Induced cis–trans Isomerization

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