Regulating signal enhancement with coordination-coupled deprotonation of a hydrazone switch

Foy, Justin T.; Ray, Debdas; Aprahamian, Ivan

doi:10.1039/c4sc02882a

Cited by 47 publications

(33 citation statements)

References 61 publications

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“…459 − 461 The Aprahamian group has studied the E / Z isomerization of hydrazones using chemical switching inputs such as protons and zinc ions. 462 − 467 …”

Section: Controlling Motion In Covalently Bonded Molecular Systemsmentioning

confidence: 99%

Artificial Molecular Machines

et al. 2015

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“…459 − 461 The Aprahamian group has studied the E / Z isomerization of hydrazones using chemical switching inputs such as protons and zinc ions. 462 − 467 …”

Section: Controlling Motion In Covalently Bonded Molecular Systemsmentioning

confidence: 99%

Artificial Molecular Machines

et al. 2015

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“…In the rotary switches, where the axle is a C=N bond, the proton is transferred between oxygen atoms belonging either to β-dicarbonyl groups ( 2 in Scheme 2 as an example) [ 25 , 26 , 27 , 28 ] or 4-hydroxycoumarin [ 29 , 30 , 31 ], or proton transfer proceeds between oxygen and nitrogen in the switches designed by Aprahamian et al [ 32 , 33 , 34 , 35 ]. The rotary switches operate mainly in ground state through acid/base catalyzed tautomerism [ 32 ].…”

Section: Introductionmentioning

confidence: 99%

8-(Pyridin-2-yl)quinolin-7-ol as a Platform for Conjugated Proton Cranes: A DFT Structural Design

Georgiev

Antonov

2020

Micromachines

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Theoretical design of conjugated proton cranes, based on 7-hydroxyquinoline as a tautomeric sub-unit, has been attempted by using ground and excited state density functional theory (DFT) calculations in various environments. The proton crane action request existence of a single enol tautomer in ground state, which under excitation goes to the excited keto tautomer through a series of consecutive excited-state intramolecular proton transfer (ESIPT) steps with the participation of the crane sub-unit. A series of substituted pyridines was used as crane sub-units and the corresponding donor-acceptor interactions were evaluated. The results suggest that the introduction of strong electron donor substituents in the pyridine ring creates optimal conditions for 8-(pyridin-2-yl)quinolin-7-ols to act as proton cranes.

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“…range of physical processes and chemical triggers to manipulate a variety of intrinsic molecular characteristics. For instance, isomerization reactions [13] driven by changes in pH, [14,15] light [16,12,15] or coordination of metal cations, [17] as well as redox processes [18,19] among others.…”

Section: Introductionmentioning

confidence: 99%

Multiple Reversible Dynamics of Pyrimidine Based Acylhydrazones

et al. 2020

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We employed (Z)‐N'‐[phenyl(pyrimidin‐2‐yl)methylene]nicotinohydrazide (2) and (Z)‐4‐(dimethylamino)‐N'‐[phenyl(pyrimidin‐2‐yl)methylene]benzohydrazide (3) as cores of dynamic chemical systems whose different states are modulated, in a reversible fashion, through specific physical and chemical stimuli. The structure of the compounds was determined by Nuclear Magnetic Resonance (NMR) techniques (1D and 2D) and confirmed by single‐crystal X‐ray diffraction. By Variable temperature (VT) 1H NMR experiments and DFT calculations, the conformational isomerism of 2 was studied and added as an additional input for the dynamic system. Additionally, 2 exhibits configurational E/Z isomerization mediated by pH variations and UV light. On the other hand, configurational isomerism locks an unlocks a tridentate pocket for metal cation coordination in both 2 and 3. All the different dynamic states configurational/conformational isomerism and locked and unlocked coordination constitute a development in the field of systems of multiple dynamics suitable for molecular machines.

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Regulating signal enhancement with coordination-coupled deprotonation of a hydrazone switch

Abstract: Regulating signal amplification using a switchable catalytic cycle.

Cited by 47 publications

References 61 publications

Artificial Molecular Machines

Artificial Molecular Machines

8-(Pyridin-2-yl)quinolin-7-ol as a Platform for Conjugated Proton Cranes: A DFT Structural Design

Multiple Reversible Dynamics of Pyrimidine Based Acylhydrazones

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