A Click Chemistry Approach to 5,5′-Disubstituted-3,3′-Bisisoxazoles from Dichloroglyoxime and Alkynes: Luminescent Organometallic Iridium and Rhenium Bisisoxazole Complexes

Peet, Phillip L. van der; Connell, Timothy U.; Gunawan, Christian; White, Jonathan M.; Donnelly, Paul S.; Williams, Spencer J.

doi:10.1021/jo4008755

Cited by 32 publications

(16 citation statements)

References 35 publications

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“…However, other polyazaheterocycles have also been developed, such as 1-R-4-(2-pyridyl)-1,2,3-triazole (pyta) and its derivatives [46][47][48]. More recently, Re(I) tricarbonyl complexes incorporating 5,5'-disubstituted 3,3'-bisisoxazole have also been described [49]. Modifications of the X ligand may also alter the luminescence properties of the complex.…”

Section: Spectroscopic Properties Of Luminescent Re(i) Tricarbonyl Comentioning

confidence: 99%

Re(I) carbonyl complexes: Multimodal platforms for inorganic chemical biology

Hostachy

Policar

Delsuc

2017

Coordination Chemistry Reviews

113

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Bio-imaging, by enabling the visualization of biomolecules of interest, has proved to be highly informative in the study of biological processes. Although fluorescence microscopy is probably one of the most used techniques, alternative methods of imaging, providing complementary information, are emerging. In this context, metal complexes represent valuable platforms for multimodal imaging, since they may combine interesting spectroscopic features and biologically relevant functionalization on a single molecular core. In particular, d6 low-spin rhenium tri-carbonyl complexes display unique luminescence and vibrational properties, and can be readily functionalized. Here we review their applications and potential as probes or drugs relying on their photophysical properties, before focusing on their use as multimodal probes for the labelling and imaging of peptides and proteins.

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Section: Spectroscopic Properties Of Luminescent Re(i) Tricarbonyl Comentioning

confidence: 99%

Re(I) carbonyl complexes: Multimodal platforms for inorganic chemical biology

Hostachy

Policar

Delsuc

2017

Coordination Chemistry Reviews

113

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“…[9] Ac ommon intermediate containing the hydroximoyl chloride moiety that is found in energetic syntheses is dichloroglyoxime (2). [10] Recent reports have identified ac hlorine-gas-free approach to this material [11] and furtherp rocess improvements that reliably providem aterial of ah igh purity under safer conditions. [12] We chose this latter method, detailedinScheme 1, toward making our isoxazole-based energetic material.…”

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confidence: 99%

Synthesis of bis‐Isoxazole‐bis‐Methylene Dinitrate: A Potential Nitrate Plasticizer and Melt‐Castable Energetic Material

et al. 2016

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The efficient and scalable synthesis of 3,3'-bis-isoxazole-5,5'bis-methylene dinitrate and its energetic properties are described. The material has favorable sensitivity properties;e nergetic properties point toward its potentiala sb oth am elt-castable secondary explosive and as ap ropellant plasticizer.The development of high-energy-density materials (HEDMs) [1] with good performance and low sensitivity is ac ommon goal amongstt hose with an interest in the field of energetic materials. HEDMs are divided into two main groups:e xplosives and propellants. Explosive materials contain as ignificant amount of potentiale nergy that produces as ignificant amount of light, heat, sound,a nd pressure when this energy is released suddenly.W hen this phenomenon occurs,i ti sk nown as an explosion. Ap ropellant is an energetic substance that is used to project av ehicle, bullet, or other object, typically through the formationo fhot, low-molecular-weight gases.Twor espective subareaso fe xplosives and propellants are melt-castable materials and energetic plasticizers.A ccording to the review by Ravi and co-workers, [2] an ideal melt-cast material is defined as having al ow vapor pressure (inhalation toxicity), am elting point between 70 and 120 8C, as ignificant difference between the melting temperature and the temperature of decomposition, ah igh density,l ow sensitivity,a nd a" greener" synthesis. Traditional melt-cast materials are based on trinitrotoluene (TNT), but environmental concerns have led to its replacement with dinitroanisole (DNAN)-based melt-castable eutecticf ormulations. [3] However,D NAN, with ad ensity of 1.52 gcm À3 ,a nd ad etonation velocity of 5670 ms À1 ,i saless powerful explosive than TNT. [4] Thus, there is an interest in de-

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“…The isoxazole ring has a nonbonded electron lone pair, and the carbon atoms that make up its molecular structure allow for the introduction of alkyl nitrate pendant chains to a greater extent than tetrazoles or triazoles. Although terminal alkynes and electron-deficient internal alkynes react readily under mild conditions with hydroximoyl chlorides to give disubstituted and trisubstituted isoxazoles, [16,17] electron-rich internal alkynes are more difficult substrates. [16] In light of this, it was believed that the tetrakis(methyl nitrate) derivative would be a worthwhile target due to its higher projected performance, because the number of alkyl nitrate pendant chains would be maximized ( Figure 1).…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Biisoxazoletetrakis(methyl nitrate): A Potential Nitrate Plasticizer and Highly Explosive Material

et al. 2017

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The efficient and scalable synthesis of 3,3′‐biisoxazole‐4,4′,5,5′‐tetrakis(methyl nitrate) and its energetic properties are described. The synthesis features a metal‐free [3+2] cycloaddition of an electron‐rich internal alkyne and a nitrile oxide by simple heating, without using halogenated solvents. The material has favorable sensitivity properties, and its energetic properties point toward its potential as a nitrate plasticizer and highly explosive material.

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A Click Chemistry Approach to 5,5′-Disubstituted-3,3′-Bisisoxazoles from Dichloroglyoxime and Alkynes: Luminescent Organometallic Iridium and Rhenium Bisisoxazole Complexes

Cited by 32 publications

References 35 publications

Re(I) carbonyl complexes: Multimodal platforms for inorganic chemical biology

Re(I) carbonyl complexes: Multimodal platforms for inorganic chemical biology

Synthesis of bis‐Isoxazole‐bis‐Methylene Dinitrate: A Potential Nitrate Plasticizer and Melt‐Castable Energetic Material

Synthesis of Biisoxazoletetrakis(methyl nitrate): A Potential Nitrate Plasticizer and Highly Explosive Material

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