Synthesis of Isoxazolopyridobicyclooxacalix[4]arenes: A New Family of Heteracalixarene Systems

Ferrini, Serena; Fusi, Stefania; Giorgi, Gianluca; Ponticelli, Fabio

doi:10.1002/ejoc.200800714

Cited by 20 publications

(4 citation statements)

References 45 publications

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“…In 2005, Katz reported the synthesis of D 3 h ‐symmetric bicyclic oxacalixarenes, a type of small cage molecule, from the reaction of phloroglucinol with activated 1,3‐difluorobenzenes or 2,5‐dichloropyridines 21. The use of 4,6‐dichloro‐3‐methylisoxazolo[4,5‐ c ]pyridine instead of activated 2,5‐dichloropyridines leads to the formation of similar small cage molecules 22. We have reported the synthesis of oxygen‐bridged bicyclcocalixaromatics from phloroglucinol and cyanuric chloride 14a.…”

Section: Introductionmentioning

confidence: 99%

Electric Double‐Layer Capacitors Based on Highly Graphitized Nanoporous Carbons Derived from ZIF‐67

Torad

Salunkhe

et al. 2014

Chemistry A European J

443

187

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Nanoporous carbons (NPCs) have large specific surface areas, good electrical and thermal conductivity, and both chemical and mechanical stability, which facilitate their use in energy storage device applications. In the present study, highly graphitized NPCs are synthesized by one-step direct carbonization of cobalt-containing zeolitic imidazolate framework-67 (ZIF-67). After chemical etching, the deposited Co content can be completely removed to prepare pure NPCs with high specific surface area, large pore volume, and intrinsic electrical conductivity (high content of sp(2) -bonded carbons). A detailed electrochemical study is performed using cyclic voltammetry and galvanostatic charge-discharge measurements. Our NPC is very promising for efficient electrodes for high-performance supercapacitor applications. A maximum specific capacitance of 238 F g(-1) is observed at a scan rate of 20 mV s(-1) . This value is very high compared to previous works on carbon-based electric double layer capacitors.

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Section: Introductionmentioning

confidence: 99%

Electric Double‐Layer Capacitors Based on Highly Graphitized Nanoporous Carbons Derived from ZIF‐67

Torad

Salunkhe

et al. 2014

Chemistry A European J

443

187

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“…For example, a few heteracalixazacrowns and bis-heteracalixaromatics of a large and tunable cavity have been prepared efficiently from the aromatic nucleophilic substitution reactions of parent oxacalix[2]arene[2]triazine and -[2]pyrimidine derivatives with the appropriate diamines. Recently, we and other groups have reported the synthesis of oxygen-bridged bicyclcocalixaromatics starting from phloroglucinol and cyanuric chloride or 2,6-dihalopyridine derivatives. , The molecules, however, have a very small cavity and therefore have very limited applications . Our interest in molecular cages ,, has led us to undertake the current study.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Functionalization of Heteroatom-Bridged Bicyclocalixaromatics, Large Molecular Triangular Prisms with Electron-Rich and -Deficient Aromatic Interiors

et al. 2011

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The synthesis and functionalization of oxygen and nitrogen atom bridged bicyclocalixaromatics of triangular prism structures are reported. By means of a fragment coupling approach, molecular triangular prisms of electron-rich and electron-deficient aromatic interiors were prepared using 1,3,5-tri(p-hydroxyphenyl)benzene and 2,4,6-tri(p-aminophenyl)triazine as base units and chlorotriazines as pillars. Aromatic nucleophilic substitution reaction of chlorotriazine moieties with functionalized amines led to triangular prisms with functionalizations on the peripheral edge positions, while functionalized triangular prisms on the vertex nitrogen positions were obtained using 2,4,6-tri[(p-allylamino)phenyl]triazine derivative as a starting material. Symmetrical and distorted molecular triangular prisms in the solid state were revealed by X-ray crystallography. As evidenced by NMR spectroscopic data, however, all cage molecules synthesized most probably adopted highly symmetric triangular prism structures in solution phase. The functionalized shape-persistent triangular prism structures might find applications in molecular recognition and in the construction of higher and more sophisticated molecular architectures in supramolecular chemistry.

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“…On the basis of previous work by Ponticelli and co‐workers, in which DFT calculations were used to confirm that the orientation of an isoxazolopyridine building block has only a minor effect on the stability of bicyclooxacalix[4]arene regioisomers,8r it may be presumed that both oxacalix[2]arene[2]quinazoline isomers will have almost the same energy. From the performed reactions so far (Table 1, Entries 1–7), it can be seen that the anti ‐cyclotetramer is generally obtained in slight excess and the isomeric ratio is undergoing rather small fluctuations.…”

Section: Resultsmentioning

confidence: 99%

Synthetic Exploration of Oxacalix[2]arene[2]quinazolines

et al. 2010

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Synthesis of Isoxazolopyridobicyclooxacalix[4]arenes: A New Family of Heteracalixarene Systems

Cited by 20 publications

References 45 publications

Electric Double‐Layer Capacitors Based on Highly Graphitized Nanoporous Carbons Derived from ZIF‐67

Electric Double‐Layer Capacitors Based on Highly Graphitized Nanoporous Carbons Derived from ZIF‐67

Synthesis and Functionalization of Heteroatom-Bridged Bicyclocalixaromatics, Large Molecular Triangular Prisms with Electron-Rich and -Deficient Aromatic Interiors

Synthetic Exploration of Oxacalix[2]arene[2]quinazolines

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