Inclusion of Cavitands and Calix[4]arenes into a Metallobridged <i>para</i>‐(1<i>H</i>‐Imidazo[4,5‐f][3,8]phenanthrolin‐2‐yl)‐Expanded Calix[4]arene

Botana, Enrique; Silva, Eric Da; Benet‐Buchholz, Jordi; Ballester, Pedro J.; Mendoza, Javier de

doi:10.1002/ange.200603180

Cited by 22 publications

(4 citation statements)

References 23 publications

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“…The IE and EA for the eight organic compounds have been calculated and are listed in Table . To validate the calculated results and show the phase state of the organic materials, available experimental data − of IE, EA and melting points are also included in Table . We can find in Table that the B3LYP-D scheme predicts very accurate IE whereas it substantially underestimates the EA.…”

Section: Resultsmentioning

confidence: 99%

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Binding Energy and Work Function of Organic Electrode Materials Phenanthraquinone, Pyromellitic Dianhydride and Their Derivatives Adsorbed on Graphene

2014

ACS Appl. Mater. Interfaces

102

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Electroactive organic compounds are a novel group of green cathode materials for rechargeable metal-ion batteries. However, the organic battery life is short because the organic compounds can be dissolved by nonaqueous electrolytes. Here a comparative investigation of phenanthraquinone (PQ), pyromellitic dianhydride (PMDA) and their derivatives, i.e., benzo[1,2-b:4,3-b']difuran-4,5-dione (BDFD), benzo[1,2-b:4,3-b']dithiophene-4,5-quinone (BDTQ), 3,8-phenanthroline-5,6-dione (PAD), pyromellitic dithioanhydride (PMDT), pyromellitic diimide (PMDI) and 1,4,5,8-anthracenetetrone (ATO), adsorbed on graphene is performed using a density functional theory (DFT) with a van der Waals (vdW) dispersion-correction. The computed results show a strong physisorption with the binding energies between 1.10 and 1.56 eV. A sequence of the calculated binding energies from weak to strong is found to be BDFD < BDTQ < PMDA ≤ PMDI < PMDT < PQ < PAD < ATO. The formation of stable organic molecule-graphene nanocomposites can prevent the dissolution of the eight organic compounds in nonaqueous electrolyte and hence improve cycling performance of batteries. In addition, the work functions for the nanocomposites are found to be strongly affected by the work function of each organic compound. To understand the DFT results, a novel simple expression is proposed to predict the work function of the nanocomposites from the interfacial dipole and the work functions of the isolated graphene nanosheet and organic molecules. The predicted work functions for the nanocomposites from the new equation agree quite well with the values calculated from the vdW dispersion-corrected DFT.

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Section: Resultsmentioning

confidence: 99%

“… d Experimental data from Potapov and Sorokin e Experimental data from Botana et al f Experimental data from Sakai g Experimental data from Lawton and McRitche …”

Section: Resultsmentioning

confidence: 99%

Binding Energy and Work Function of Organic Electrode Materials Phenanthraquinone, Pyromellitic Dianhydride and Their Derivatives Adsorbed on Graphene

2014

ACS Appl. Mater. Interfaces

102

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“…It is of continuing interest to design and synthesize novel macrocyclic host molecules because of their important roles in supramolecular chemistry. The successful examples include crown ethers, − cyclodextrins, cucurbiturils, calixarenes, − and their structurally similar scaffolds. − Currently a new class of [1 n ]paracyclophanes , is growing with similar composition but different structural features compared with calixarenes. This new class of macrocyclic molecules are made up of hydroquinone units linked by methylene bridges at para positions.…”

Section: Introductionmentioning

confidence: 99%

Pillararenes, A New Class of Macrocycles for Supramolecular Chemistry

et al. 2012

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Because of the importance of novel macrocycles in supramolecular science, interest in the preparation of these substances has grown considerably. However, the discovery of a new class of macrocycles presents challenges because of the need for routes to further functionalization of these molecules and good host-guest complexation. Furthermore, useful macrocylic hosts must be easily synthesized in large quantities. With these issues in mind, the recently discovered pillararenes attracted our attention. These macrocycles contain hydroquinone units linked by methylene bridges at para positions. Although the composition of pillararenes is similar to that of calixarenes, they have different structural characteristics. One conformationally stable member of this family is pillar[5]arene, which consists of five hydroquinone units. The symmetrical pillar architecture and electron-donating cavities of these macrocycles are particularly intriguing and afford them with some special and interesting physical, chemical, and host-guest properties. Due to these features and their easy accessibility, pillararenes, especially pillar[5]arenes, have been actively studied and rapidly developed within the last 4 years. In this Account, we provide a comprehensive overview of pillararene chemistry, summarizing our results along with related studies from other researchers. We describe strategies for the synthesis, isomerization, and functionalization of pillararenes. We also discuss their macrocyclic cavity sizes, their host-guest properties, and their self-assembly into supramolecular polymers. The hydroxyl groups of the pillararenes can be modified at all positions or selectively on one or two positions. Through a variety of functionalizations, researchers have developed many pillararene derivatives that exhibit very interesting host-guest properties both in organic solvents and in aqueous media. Guest molecules include electron acceptors such as viologen derivatives and (bis)imidazolium cations and alkyl chain derivatives such as n-hexane, alkanediamines, n-octyltrimethyl ammonium, and neutral bis(imidazole) derivatives. These host-guest studies have led to the fabrication of (pseudo)rotaxanes or poly(pseudo)rotaxanes, supramolecular dimers or polymers, artificial transmembrane proton channels, fluorescent sensors, and other functional materials.

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“…The reaction of 28 and [Re(CO) 5 Br] gives rise to a metallocavitand 28 ·Re 4 complex [94] which has been characterized by ESI-MS, IR and NMR spectroscopies. This metallocavitand exhibits a deep, square pyramidal cavity which can fit for molecules of complementary size and shape.…”

Section: Molecular Recognition Based Upon Extended Calix[4]arenesmentioning

confidence: 99%

Extended Calix[4]arene-Based Receptors for Molecular Recognition and Sensing

Wong

2008

Sensors

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Recent advances in the area of recognition and sensing have shown that artificial receptors derived from extended calix[4]arenes bearing multiple π-conjugated fluorophoric or chromophoric systems have found useful to enhance binding affinity, selectivity and sensitivity for recognition and sensing of a targeted ion or molecule. A comprehensive review of various π-conjugation-extended calix[4]arene-based receptors with the highlight on the design and binding characterization for recognition and sensing is presented.

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Inclusion of Cavitands and Calix[4]arenes into a Metallobridged para‐(1H‐Imidazo[4,5‐f][3,8]phenanthrolin‐2‐yl)‐Expanded Calix[4]arene

Cited by 22 publications

References 23 publications

Binding Energy and Work Function of Organic Electrode Materials Phenanthraquinone, Pyromellitic Dianhydride and Their Derivatives Adsorbed on Graphene

Binding Energy and Work Function of Organic Electrode Materials Phenanthraquinone, Pyromellitic Dianhydride and Their Derivatives Adsorbed on Graphene

Pillararenes, A New Class of Macrocycles for Supramolecular Chemistry

Extended Calix[4]arene-Based Receptors for Molecular Recognition and Sensing

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