The role of high pressure methods in organic chemistry

Isaacs, Neil S.

doi:10.1016/s0040-4020(01)82392-9

Cited by 119 publications

(27 citation statements)

References 59 publications

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“…Activation volumes as large as À70 cm 3 mol À1 are known. [9] Following on the heels of these studies, Grieco attempted to connect reaction promotion by high external static pressures to the high internal pressure in solvents like water. [10] He reported significant rate accelerations for Diels-Alder reactions in 5 m LiClO 4 /diethyl ether, initially implying that such solutions compress reactants in a manner analogous to external pressure.…”

mentioning

confidence: 99%

Acceleration of Organic Reactions through Aqueous Solvent Effects

Pirrung

2006

Chemistry A European J

342

119

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mentioning

confidence: 99%

Acceleration of Organic Reactions through Aqueous Solvent Effects

Pirrung

2006

Chemistry A European J

342

119

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“…The monofunctionalized [2]catenanes 9‚4PF 6 and 10‚-4PF 6 , incorporating a carboxylic acid function and a hydroxymethyl group, respectively, on the tetracationic cyclophane component were self-assembled using ultrahigh pressure conditions, 18 9‚4PF 6 or 10‚4PF 6 , respectively, in yields of 15% in both instances.…”

Section: Resultsmentioning

confidence: 99%

Self-Assembly of Functionalized [2]Catenanes Bearing a Reactive Functional Group on either One or Both Macrocyclic ComponentsFrom Monomeric [2]Catenanes to Polycatenanes

Menzer¹,

White²,

Williams³

et al. 1998

Macromolecules

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A series of mono-and difunctionalized [2]catenanes, incorporating a bipyridinium-based cyclophane component interlocked with a dioxyarene-based macrocyclic polyether, have been selfassembled. The methodology relies upon the complementarity between the π-electron-deficient and the π-electron-rich macrocyclic components. Hydrogen-bonding interactions between the acidic hydrogen atoms on the bipyridinium units and the polyether oxygen atoms, as well as π-π stacking and edge-toface T-type interactions between the complementary aromatic units, are responsible for these self-assembly processes. These [2]catenanes have been designed in order to locate one reactive functional groupseither a hydroxyl group or a carboxylic acid functionsonto one or both macrocyclic components. In principle, polymerization or copolymerization of these monomeric [2]catenanes can be realized by condensations at the reactive functional groups to generate main-chain, side-chain, and dendritic polycatenanes. Indeed, the versatility of this design logic has been demonstrated by some preliminary experiments. A mainchain oligo[2]catenane incorporating 17 repeating units connected by urethane linkages was synthesized by the condensation of a monomeric difunctionalized [2]catenane bearing one hydroxymethyl group on each of its two macrocyclic components with a diisocyanate derivative. The geometries adopted in the solid state by some of the monomeric [2]catenanes were examined by single-crystal X-ray analyses. Interestingly, in the case of a monofunctionalized [2]catenane bearing one carboxylic acid group on its π-electron-rich macrocyclic component, pseudobis [2]catenanes are observed in the solid state as a result of the formation of hydrogen-bonded dimers between the carboxylic acid groups of adjacent molecules. IntroductionThe interest of many investigators is now being focused on the synthesis of a new class of polymeric materials composed of macrocyclic components linked by mechanical bondssnamely, polycatenanes. 1 The main-chain polycatenane (a), schematically represented in Figure 1, is the equivalent of a chain at the molecular level. However, its synthesis is not easily achievable and the highest homolog of this class of compounds selfassembled so far is the so-called Olympiadane 2 snamely, a [5]catenane incorporating five interlocked rings in a linear array. The main-chain polycatenanes (b) and (c) feature the alternation of covalent and mechanical bondssthe latter embellished with noncovalent bonding interactionssalong their main axes. These compounds can be synthesized, in principle, by polymerization or copolymerization, respectively, of [2]catenane 3 monomers possessing one reactive functional group on each of the two macrocyclic components. Similarly, monofunctionalized [2]catenane monomers can be grafted on to a polymeric backbone or attached to a highly branched core to afford side-chain (d) or dendritic polycatenanes.Recently, we have developed 4 a synthetic methodology to self-assemble 5 [n]catenanes incorporating π-electron-

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“…[2,15] A few studies involving the phase transitions of organic crystals at high pressure have been reported in recent years. [16,17] Unlike phase transitions occurring in inorganic crystals at high pressure, however, most of the phase transitions occurring in organic compounds are reversible when the pressure is released.…”

Section: High Pressure Effects On the Emission Properties And Crystalmentioning

confidence: 99%

High Pressure Effects on the Emission Properties and Crystal Structure of Coumarin 120

Zhong

et al. 2004

ChemPhysChem

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The role of high pressure methods in organic chemistry

Cited by 119 publications

References 59 publications

Acceleration of Organic Reactions through Aqueous Solvent Effects

Acceleration of Organic Reactions through Aqueous Solvent Effects

Self-Assembly of Functionalized [2]Catenanes Bearing a Reactive Functional Group on either One or Both Macrocyclic ComponentsFrom Monomeric [2]Catenanes to Polycatenanes

High Pressure Effects on the Emission Properties and Crystal Structure of Coumarin 120

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