A β-amino-cyclodextrin monolayer-modified Au electrode: a command surface for the amperometric and microgravimetric transduction of optical signals recorded by a photoisomerizable bipyridinium–azobenzene diad

Lahav, Michal; Koodali, Ranjit T.; Katz, Eugenii; Willner, Itamar

doi:10.1039/a606189c

Cited by 63 publications

(32 citation statements)

References 16 publications

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“…The light‐switched dispersion of SWNTs in water is ascribed to the polymer with light‐responsive azobenzene group and its host–guest interaction with CD absorbed onto surface of SWNTs. As illustrated in Scheme 2b, without UV irradiation, the azobenzene group exhibits trans form, and then SWNTs were dispersed because of the association constant ( K a ) of β‐CD for trans azobenzene is as high as 1700 M −1 . However, after being treated with UV irradiation, the azobenzene group is isomerized from trans to cis form, leading to the disassembly of host–guest interaction and aggregation of SWNTs, as the K a of β‐CD for cis azobenzene is only 180 M −1 .…”

Section: Resultsmentioning

confidence: 99%

Light‐Switchable Single‐Walled Carbon Nanotubes Based on Host–Guest Chemistry

Guo

Feng

Zhu

et al. 2013

Adv Funct Materials

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A new type of light-switchable "smart" single-walled carbon nanotube (SWNTs) is developed by the reversible host-guest interaction between azobenzene-terminal PEO (AzoPEO) and pyrene-labeled host attached on the sidewalls of nanotubes via ππ stacking. The SWNTs hybrids not only are well dispersed in pure water, but also exhibit switchable dispersion/aggregation states upon the alternate irradiation of UV and visible light. Moreover, the SWNTs hybrids dispersion is preliminarily used as coating fl uid to form transparent conductive fi lms. The dispersant AzoPEO is removed by the contamination-free UV treatment, decreasing the resistance of the fi lms. This kind of light-switchable SWNTs hybrids, possessing a ''green'' trigger and intact structure of the nanotube, may fi nd potential applications in sensor of biomedicines, device fabrication, etc. Additionally, such a reversible hostguest interaction system may open up the possibility to control the dispersion state of SWNTs by other common polymers. Scheme 1 . The synthesis strategies for a) azobenzene-containing PEO (AzoPEO), and b) pyrene-labelled β -cyclodextrin (p-CD).

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Section: Resultsmentioning

confidence: 99%

Light‐Switchable Single‐Walled Carbon Nanotubes Based on Host–Guest Chemistry

Guo

Feng

Zhu

et al. 2013

Adv Funct Materials

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“…The molecular size/shape‐controlled processes discussed above have been extended to the study of the complex formation between azobenzene‐functionalized viologen with surface‐immobilized cyclodextrin receptors , Figure . The β‐aminocyclodextrin receptor units were covalently immobilized on a Au electrode surface by reacting their amino groups with dithiobis‐(succinimidyl propionate) self‐assembled on the electrode surface .…”

Section: Azobenzene‐based Photoelectrochemical Switchesmentioning

confidence: 94%

“…As expected, the complex formation was controlled by the size/shape of the azobenzene‐viologen ligand. The photo‐induced isomerization of the azobenzene units resulted in the change of their size/shape, thus affecting the complex formation and demonstrating different association constants, K a , 3000 and 7000 M −1 for the cis ‐ and trans ‐isomeric states, respectively , Figure . The complex formation was analyzed by cyclic voltammetry following the redox response of the viologen units associated with cyclodextrin, Figure A, or measuring mass of the associated ligands using quartz crystal microbalance (QCM), Figure B.…”

Section: Azobenzene‐based Photoelectrochemical Switchesmentioning

confidence: 99%

Modified Electrodes and Electrochemical Systems Switchable by Light Signals

Katz¹

2018

Electroanalysis

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This article is an overview of extensive research efforts in many laboratories in the last two decades in the area of light‐switchable electrochemical systems and modified electrodes. Electrochemical reactions, including electrocatalytic and bioelectrocatalytic processes, have been reversibly activated and inhibited upon irradiation with light at different wavelengths. In order to realize these light activated or inhibited processes, the electrodes or/and reacting molecules were functionalized with photoisomerizable molecules including various derivatives of diarylethene, phenoxynaphthacenequinone, azobenzene and spiropyran/merocyanine. Photochemical reactions of these species resulted in change of their redox activity, conformation and electrical charge. All these changes affected electrode surfaces or (bio)molecules resulting in switching ON‐OFF corresponding (bio)electrochemical processes. Various systems based on different light‐controlled reactions are reviewed and discussed with specific examples and with many illustrating figures. Possible extensions of the research area and future applications are briefly overviewed in the conclusion section. The present comprehensive review is addressed to a broad scientific community, including newcomers to the area.

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“…Im Unterschied zum vorherigen Beispiel, bei dem die elektrostatischen Wechselwirkungen zwischen den Komponenten photochemisch moduliert wurden, nutzten Willner et al die photochemisch induzierte Isomerisierung der Azobenzoleinheit von 23 , um das Auffädeln und Abfädeln eines immobilisierten Pseudorotaxans zu steuern (Abbildung 12 a). Sie entwickelten Oberflächen, in denen die Bindung zwischen einer β‐Cyclodextrin(CD)‐modifizierten Goldelektrode 24 und dem photoisomerisierbaren, elektroaktiven Azobenzolderivat 23 photochemisch gesteuert werden kann 25. Die als Wirt fungierende, nicht elektroaktive Cyclodextrineinheit von 24 hat einen Hohlraum, in den die trans ‐Form des Azobenzolderivats ( 23 trans ) unter Bildung eines Pseudorotaxans effektiv einfädeln kann (Abildung 12 b).…”

Section: Photochemische Steuerung Von Wirt‐gast‐wechselwirkungenunclassified

Elektrochemische und photochemische Steuerung der Wirt‐Gast‐Komplexierung an Oberflächen

Cooke¹

2003

Angewandte Chemie

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Der Einsatz von Elektro‐ und Photochemie zur Modulation supramolekularer Wechselwirkungen zwischen Wirt‐Gast‐Systemen in Lösung ist ein aktuelles Forschungsgebiet. Die Geschwindigkeit und Reversibilität elektrochemisch oder photochemisch ausgelöster Wechselwirkungen ermöglichten Aufbau und Modulation neuartiger molekularer Maschinen in Lösung. In den letzten Jahren wurden große Fortschritte bei der Übertragung dieser Systeme auf die Festphase erzielt. Dadurch wurde die Entwicklung von Bausteinen erleichtert, die auf einen Reiz als elektronische Einheit reagieren. So können Oberflächen aufgebaut werden, die auf äußere Signale reagieren. Diese Systeme können in hoch entwickelten Materialien für die Nanotechnologie eingesetzt werden.

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A β-amino-cyclodextrin monolayer-modified Au electrode: a command surface for the amperometric and microgravimetric transduction of optical signals recorded by a photoisomerizable bipyridinium–azobenzene diad

Cited by 63 publications

References 16 publications

Light‐Switchable Single‐Walled Carbon Nanotubes Based on Host–Guest Chemistry

Light‐Switchable Single‐Walled Carbon Nanotubes Based on Host–Guest Chemistry

Modified Electrodes and Electrochemical Systems Switchable by Light Signals

Elektrochemische und photochemische Steuerung der Wirt‐Gast‐Komplexierung an Oberflächen

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