Supramolecular Detection of Metal Ion Binding: Ligand Conformational Control of Cholesteric Induction in Nematic Liquid Crystalline Phases

Zahn, Steffen; Proni, Gloria; Spada, Gian Piero; Canary, James W.

doi:10.1002/1521-3765(20010105)7:1<88::aid-chem88>3.0.co;2-0

Cited by 31 publications

(5 citation statements)

References 31 publications

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“…Namely, the redox active moiety should be located in close proximity to the chiral center, so that the HTP value of the dopant changes responsively to the redox events. Note that the circular dichroism (CD) spectral profile of Fc D (Figure S4b) was insensitive to its oxidation, suggesting that the redox events are not accompanied by a conformational change of the binaphthyl unit. , This possibility was supported computationally (Figure S23). Hence, the decrease in the HTP value upon oxidation of Fc D described above is most likely due to the disturbance of the helical ordering of 5OCB through an ion–dipole interaction with the ferrocenium ion. , …”

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confidence: 83%

Redox-Responsive Chiral Dopant for Quick Electrochemical Color Modulation of Cholesteric Liquid Crystal

et al. 2018

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Here, we report the first redox-active chiral dopant D, which electrically alters its helical twisting power (HTP) for a cholesteric liquid crystalline (LC) medium and quickly changes the reflection color.D is composed of an axially chiral binaphthyl unit in conjunction with a redox-active ferrocene unit. A cholesteric LC phase of 4'-pentyloxy-4-cyanobiphenyl, doped with D (3.0 mol %), developed a blue reflection color. When nitrosyl tetrafluoroborate, a one-electron oxidant, was added to this cholesteric LC phase,D was oxidized to decrease its original HTP value by 13%, so that a green reflection color was developed. In the presence of a supporting electrolyte, the reflection color was electrochemically modulated using a sandwich-type glass cell with indium tin oxide electrodes. In quick response to the applied voltage of +1.5 V, the reflection color changed from blue to green within 0.4 s. When 0 V was applied, the reflection color returned to its original blue color. The D-doped cholesteric LC is characterized by its fastest electrochemical response and lowest operating voltage among those reported for electrically driven cholesteric LC devices.

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confidence: 83%

Redox-Responsive Chiral Dopant for Quick Electrochemical Color Modulation of Cholesteric Liquid Crystal

et al. 2018

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“…Redox changes (Cu(I)/Cu(II)) also gave large changes in twisting power of these complexes to torque a nematic into a cholesteric liquid crystalline phase [ 81 ]. The handedness of the induced cholesteric phase was related to the stereochemistry of the complex.…”

Section: Chemically Triggered Chiroptical Switchesmentioning

confidence: 99%

Chiroptical Switches: Applications in Sensing and Catalysis

2012

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Chiroptical switches have found application in the detection of a multitude of different analytes with a high level of sensitivity and in asymmetric catalysis to offer switchable stereoselectivity. A wide range of scaffolds have been employed that respond to metals, small molecules, anions and other analytes. Not only have chiroptical systems been used to detect the presence of analytes, but also other properties such as oxidation state and other physical phenomena that influence helicity and conformation of molecules and materials. Moreover, the tunable responses of many such chiroptical switches enable them to be used in the controlled production of either enantiomer or diastereomer at will in many important organic reactions from a single chiral catalyst through selective use of a low-cost inducer: Co-catalysts (guests), metal ions, counter ions or anions, redox agents or electrochemical potential, solvents, mechanical forces, temperature or electromagnetic radiation.

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“…Such tripodal ligands were found to act as chemosensor molecules; their ability to torque a nematic into a cholesteric liquid crystalline phase increased upon complexation with copper ion [70]. Changes in overall shape of the complexes induced by different metals and counter ions were transferred sensitively to the supramolecular level, observed by proportionate changes in the degree of twisting.…”

Section: Chiroptical Tripodal Ligandsmentioning

confidence: 99%

Transition metal-based chiroptical switches for nanoscale electronics and sensors

Canary

Mortezaei

Liang

2010

Coordination Chemistry Reviews

127

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Supramolecular Detection of Metal Ion Binding: Ligand Conformational Control of Cholesteric Induction in Nematic Liquid Crystalline Phases

Cited by 31 publications

References 31 publications

Redox-Responsive Chiral Dopant for Quick Electrochemical Color Modulation of Cholesteric Liquid Crystal

Redox-Responsive Chiral Dopant for Quick Electrochemical Color Modulation of Cholesteric Liquid Crystal

Chiroptical Switches: Applications in Sensing and Catalysis

Transition metal-based chiroptical switches for nanoscale electronics and sensors

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