Design, Synthesis, Selective Recognition Properties and Targeted Drug Delivery Application

Králová, Jarmila; Kejík, Zdeněk; Břı́za, Tomáš; Kaplánek, Robert; Záruba, Кamil; Martásek, Pavel; Král, Vladimír

doi:10.1142/9789814417297_0008

Cited by 3 publications

(1 citation statement)

References 276 publications

(343 reference statements)

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“…Because of the properties outlined above, these materials are either currently found in or proposed for use in a wide range of modern devices and technologies . These include but are not limited to solar cells, − chemical sensors, − medicine, − optoelectronics, − catalysts, − and FETs. − For many of these applications, the preferred form of the compound is as a film. The electronic and mechanical properties of these films can, to a great extent, depend upon the structure of the first layer that forms the foundation for the interface between the support and the film. − Thus, in order to get optimal control over the properties of the desired device, the ability to rationally design the first monolayer of material is essential.…”

Section: Introductionmentioning

confidence: 99%

Kinetic and Thermodynamic Control in Porphyrin and Phthalocyanine Self-Assembled Monolayers

Hipps

Mazur

2017

Langmuir

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Porphyrins and phthalocyanines are ubiquitous in modern science and technology. Their stability, redox properties, and photoresponse make them candidates for numerous applications. Many of these applications rely on thin films, and these are critically dependent on the first monolayer. In this article, we focus on noncovalently bound self-assembled monolayers of porphyrins and phthalocyanines at the solution-solid interface with special emphasis on the kinetic and thermodynamic processes that define the films and their reaction chemistry. We first discuss the difference between film-formation kinetics and desorption kinetics from fully formed films. We then present evidence that many of these monolayers are controlled by adsorption kinetics and are not in thermodynamic equilibrium. Measurement of the solution-solid interface desorption energy by scanning tunneling microscopy is discussed, and data is presented for cobalt, nickel, and free base octaethylporphyrin. The activation energy for the desorption of these compounds into phenyloctane is about half of the computed desorption energy in vacuum, and this is discussed in terms of the role of the solvent. Preexponential factors are very low compared to desorption into vacuum, and this is attributed to a reduction in the entropy of activation due to the participation of solvent in the transition state. An example of the use of relative desorption kinetics to create a new binary surface structure is given. It is suggested that this is a synthesis route that may have been missed because of the large difference in solution concentrations required to drive binary film formation. Attention then turns to the axial reaction chemistry of metalloporphyrins and metallophthalocyanines supported on conducting surfaces. We show several examples of chemistry unique to the supported complexes: cases where the metal binds ligands more readily and cases where the substrate induces ligand loss. Understanding this new axial coordination chemistry is of great importance in catalysis, sensing, and the growth of 3D materials from a self-assembled template.

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Section: Introductionmentioning

confidence: 99%

Kinetic and Thermodynamic Control in Porphyrin and Phthalocyanine Self-Assembled Monolayers

Hipps

Mazur

2017

Langmuir

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Pd-catalyzed Csp 2 −H phosphonation in the meso position of porphyrins

Mikhalitsyna

Pod’yacheva

Averin

et al. 2018

J. Porphyrins Phthalocyanines

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Pd(II)-catalyzed C–H phosphonation with diethyl phosphite in the meso positions of mesityl-substituted porphyrins taken either as free base or Ni(II) and Zn(II) complexes has been investigated and the reaction conditions have been optimized. Ni(II) porphyrinates have been found to be advantageous over free porphyrins and their Zn(II) complexes. The possibility of diphosphonation was shown using 5,15-dimesityl porphyrin.

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Role of the Supporting Surface in the Thermodynamics and Cooperativity of Axial Ligand Binding to Metalloporphyrins at Interfaces

Johnson

Chilukuri

Fisherb

et al. 2022

COC

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: Metalloporphyrins have been shown to bind axial ligands in a variety of environments including the vacuum/solid and solution/solid interfaces. Understanding the dynamics of such interactions is a desideratum for the design and implementation of next generation molecular devices which draw inspiration from biological systems to accomplish diverse tasks such as molecular sensing, electron transport, and catalysis to name a few. In this article, we review the current literature of axial ligand coordination to surface-supported porphyrin receptors. We will focus on the coordination process as monitored by scanning tunneling microscopy (STM) that can yield qualitative and quantitative information on the dynamics and binding affinity at the single molecule level. In particular, we will address the role of the substrate and intermolecular interactions in influencing cooperative effects (positive or negative) in the binding affinity of adjacent molecules based on experimental evidence and theoretical calculations.

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Design, Synthesis, Selective Recognition Properties and Targeted Drug Delivery Application

Cited by 3 publications

References 276 publications

Kinetic and Thermodynamic Control in Porphyrin and Phthalocyanine Self-Assembled Monolayers

Kinetic and Thermodynamic Control in Porphyrin and Phthalocyanine Self-Assembled Monolayers

Pd-catalyzed Csp 2 −H phosphonation in the meso position of porphyrins

Role of the Supporting Surface in the Thermodynamics and Cooperativity of Axial Ligand Binding to Metalloporphyrins at Interfaces

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