“Clickable” Metal−Organic Framework

Goto, Yuta; Sato, Hiroki; Shinkai, Seiji; Sada, Kazuki

doi:10.1021/ja7114053

Cited by 275 publications

(166 citation statements)

References 21 publications

(11 reference statements)

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“…In 2008, Sada s group [21] demonstrated that a MOF composed of a strut with two benzyl azides could be chemically modified with the CuAAC reaction by using a variety of small molecule alkynes. Subsequently, in 2009, Hupp and co-workers [22] went on to show that a MOF with pendant alkyne functionalities in its struts could be functionalized in a selective manner.…”

Section: 3-dipolar Cycloadditions Of Azides With Alkynesmentioning

confidence: 99%

Reactions under the Click Chemistry Philosophy Employed in Supramolecular and Mechanostereochemical Systems

Fahrenbach

Stoddart

2011

Chemistry An Asian Journal

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On the occasion of the 10th anniversary of click chemistry FOCUS REVIEWSAbstract: Supramolecular chemistry and mechanostereochemistry have been major beneficiaries of the concepts and reactions pioneered under the "click chemistry" philosophy. The success of the copper(I) 1,3-dipolar cycloaddition between azides and alkynes, resulting in the triazole ring has inspired the application of other emerging click reactions, for example, Diels-Alder cycloadditions, thiolene/yne chemistry, and nitrile N-oxide cycloadditions, towards the creation of advanced functional supramolecular and mechanostereochemical systems. In this Focus Review, recent advances in the use of click chemistry in these fields are highlighted.

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Section: 3-dipolar Cycloadditions Of Azides With Alkynesmentioning

confidence: 99%

Reactions under the Click Chemistry Philosophy Employed in Supramolecular and Mechanostereochemical Systems

Fahrenbach

Stoddart

2011

Chemistry An Asian Journal

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“…Nowadays, there are some predominant methods that are in use to chemically modify surfaces, due to the smooth chemically conditions needed and the wide range of functional groups that can be introduced: the click chemistry [142][143] and the peptide coupling. [119] More recently, some new techniques were proposed to enhance and diversify the number of method that can be used to chemically modify surfaces.…”

Section: The Sonogashira Reactionmentioning

confidence: 99%

“…[143] Often, the first step is the introduction of a functional group via a suitable organic molecule as self assembled monolayer (SAM) on a noble metal substrate, [230][231] silicon or silicon oxide surfaces [125] [127] or as coating ligand for nanoparicles. [152] After the introduction of a chemically addressable surface layer, efficient chemical conditions such as click chemistry [142][228] [232] or peptide coupling [119] have been applied to further diversify the exposed surface functionality.…”

Section: Platinum Electrode Modificationmentioning

confidence: 99%

Shape‐Switchable Azo‐Macrocycles

et al. 2009

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The synthesis of four shape‐switchable macrocycles comprising different peripheral substituents is described. The macrocycles 1–4 consist of m‐terphenyl semicircles interlinked by two azo joints. These macrocycles were assembled from nitro‐functionalized m‐terphenyl moieties through reductive dimerization. The semicircles were assembled through Suzuki cross‐coupling reactions. The molecular weights of the macrocycles were determined by vapour pressure osmometry, because mass spectrometry failed in the cases of 2 and 3. The E → Z photoisomerization reactions were analysed by UV/Vis spectroscopy complemented by 1H NMR studies. A very slow thermal back‐reaction indicated considerable stabilization of the Z isomer. The reduced efficiency of the thermal back‐reaction probably arises from the reduced degree of freedom due to the mechanical interlinking of the two azo groups. The photostationary state consisted of all‐Z (85 %) and all‐E isomers (15 %). The E → Z transformation induced by irradiation displayed simple exponential kinetics, which indicates pairwise switching of the two azo groups in a macrocycle, at least on the timescale under investigation. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

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“…An azide-appended MOF exhibits pore surface decoration upon reaction with small alkynes 35 , whereas an MOF bearing trimethylsilane-protected acetylene units allows a selective deprotection and a selective decoration of the exterior and interior surfaces with ethidium bromide and phenyl groups, respectively, by reaction with the corresponding azide compounds 36 . Despite these achievements, density control of the functional surface groups in MOFs has not been obtained.…”

mentioning

confidence: 99%

Pore surface engineering in covalent organic frameworks

et al. 2011

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Covalent organic frameworks (CoFs) are a class of important porous materials that allow atomically precise integration of building blocks to achieve pre-designable pore size and geometry; however, pore surface engineering in CoFs remains challenging. Here we introduce pore surface engineering to CoF chemistry, which allows the controlled functionalization of CoF pore walls with organic groups. This functionalization is made possible by the use of azideappended building blocks for the synthesis of CoFs with walls to which a designable content of azide units is anchored. The azide units can then undergo a quantitative click reaction with alkynes to produce pore surfaces with desired groups and preferred densities. The diversity of click reactions performed shows that the protocol is compatible with the development of various specific surfaces in CoFs. Therefore, this methodology constitutes a step in the pore surface engineering of CoFs to realize pre-designed compositions, components and functions.

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“Clickable” Metal−Organic Framework

Cited by 275 publications

References 21 publications

Reactions under the Click Chemistry Philosophy Employed in Supramolecular and Mechanostereochemical Systems

Reactions under the Click Chemistry Philosophy Employed in Supramolecular and Mechanostereochemical Systems

Shape‐Switchable Azo‐Macrocycles

Pore surface engineering in covalent organic frameworks

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