Isolation of a Carborane‐Fused Triazole Radical Anion

Asay, Matthew; Kefalidis, Christos E.; Estrada, Jess; Weinberger, David S.; Wright, James H.; Moore, Curtis E.; Rheingold, Arnold L.; Maron, Laurent; Lavallo, Vincent

doi:10.1002/anie.201306764

Cited by 49 publications

(14 citation statements)

References 87 publications

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“…13 The ratio of monomers incorporated into the PPy backbone of the material was evaluated by UV/vis spectroscopy and turned out to be roughly 1 : 1, indicating that the rate of polymerization of both monomers is practically the same. These synthons (see Chart 5) are as follows: (i) neutral mono-substituted (19), 14 (20), 14 (21), 15 (22); 15 (ii) neutral di-substituted (23), 16 (24) 15 and (iii) anionic mono-substituted compounds (25), 14 (26). This value represents the best performance ever obtained in a heterogeneous phase using a chemical oxidant.…”

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confidence: 99%

Icosahedral boron clusters: a perfect tool for the enhancement of polymer features

et al. 2016

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Boron clusters and organic molecules display manifestly different electronic, physical, chemical and geometrical characteristics. These differences highlight the complementarity of organic synthons and boron clusters, and therefore the feasibility of producing hybrid polymers incorporating both types of fragments. This review focuses on the development of hybrid organic-inorganic π conjugated, silane, siloxane and coordination polymers containing icosahedral boron clusters in the last few decades, which have received considerable academic and technological interest due to the combination of the electronic, optical and thermal properties of traditional inorganic materials with many of the desirable properties of organic plastics, including mechanical flexibility and low production costs.

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confidence: 99%

Icosahedral boron clusters: a perfect tool for the enhancement of polymer features

et al. 2016

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“…In summary, a new class of perfunctionalized, vertex-differentiated boron clusters was developed and fully characterized. While several routes exist to achieve vertex-differentiated perfunctionalization with other boron cluster molecules with inherent asymmetry such as monocarborane, 21–25 significantly fewer synthetic pathways have been developed to form vertex-differentiated perfunctionalized dodecaborate clusters. 20,26 These NO 2 -substituted dodecaborate clusters feature higher redox potentials while retaining key beneficial traits found in their perfunctionalized [B 12 (OR) 12 ] analogues, including three distinct accessible redox states.…”

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Tuning the electrochemical potential of perfunctionalized dodecaborate clusters through vertex differentiation

et al. 2018

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We report a new class of redox-active vertex-differentiated dodecaborate clusters featuring pentafluoroaryl groups. These [B12(OR)11NO2] clusters share several unique photophysical properties with their [B12(OR)12] analogues, while exhibiting significantly higher (+0.5 V) redox potentials. This work describes the synthesis, characterization, and isolation of [B12(O-CH2C6F5)11NO2] clusters in all 3 oxidation states (dianion, radical, and neutral). Reactivity to post-functionalization with thiol species via SNAr on the pentafluoroaryl groups is also demonstrated.

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“…Note that although BÀNf used benzenes and cyclohexenes have been developed, [19] rare examples contain ap olyhedron carboranyl unit with BN fusion. [20] Sterically bulky substituents (methyl, n-/s-butyl, and phenyl) at the 2-quinolyl position afforded slightly decreased yields (7b-e), whereas tert-butyl substitution totally blocked the conversion (7f). 2-tetrahydrofuryl and 1,4-dioxan-2-yl substituents at the 2-quinolyl position were also tolerated, affording two conformational isomers in 80 and 83 % combined yields,r espectively.E ither changing the substituents at the cage-carbon site or replacing the quinolyl with pyridyl moiety afforded comparable outcomes (7i-k).…”

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confidence: 99%

Metal‐Free Oxidative B−N Coupling of nido‐Carborane with N‐Heterocycles

et al. 2019

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Ag eneral method for the oxidative substitution of nido-carborane (7,8-C 2 B 9 H 12 À )w ith N-heterocycles has been developed by using 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) as an oxidant. This metal-free B À Ncoupling strategy, in both inter-a nd intramolecular fashions,g ave rise to aw ide arrayo fc harge-compensated, boron-substituted nido-carboranes in high yields (up to 97 %) with excellent functional-group tolerance under mild reaction conditions.T he reaction mechanism was investigated by density-functional theory (DFT) calculations.Asuccessive single-electron transfer (SET), BÀH hydrogen-atom transfer (HAT), and nucleophilic attackp athway is proposed. This method provides an ew approach to nitrogen-containing carboranes with potential applications in medicine and materials.

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Isolation of a Carborane‐Fused Triazole Radical Anion

Cited by 49 publications

References 87 publications

Icosahedral boron clusters: a perfect tool for the enhancement of polymer features

Icosahedral boron clusters: a perfect tool for the enhancement of polymer features

Tuning the electrochemical potential of perfunctionalized dodecaborate clusters through vertex differentiation

Metal‐Free Oxidative B−N Coupling of nido‐Carborane with N‐Heterocycles

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