Phane nomenclature. Part II. Modification of the degree of hydrogenation and substitution derivatives of phane parent hydrides (IUPAC Recommendations 2002)

Favre, H.; Hellwinkel, Dieter; Powell, W. H.; Smith, Homer A.; Tsay, S. S.-C.

doi:10.1351/pac200274050809

Cited by 42 publications

(13 citation statements)

References 8 publications

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“…Systematic names were generated with ACD/Name [6] according to the IUPAC recommendations and were also checked manually to ensure the correct use of nomenclature within this publication [7]. The alternative name for compound 4 is according to phane nomenclature [8,9]. Product yields were not optimized.…”

Section: Methodsmentioning

confidence: 99%

“…1 H NMR spectrum (300 MHz), δ, ppm (J, Hz): 9.50 (1H, s, H-10); 9.01 (1H, s, H-4); 8.36 (1H, d, 3 J 5,6 = 9.1, H-5); 7.98 (1H, d, 3 J 6,5 = 9.1, H-6). 13 2,8-Dichloro-1,7-phenanthroline-3,9-dicarbonyl Dichloride (9). A suspension of diacid 8 (1.69 g, 5 mmol), cyclohexane (5 ml), DMF (1 drop), and SOCl 2 (10 ml) was heated at reflux for 6 h. Then excess SOCl 2 was removed under reduced pressure and the reaction mixture was stored in the refrigerator overnight.…”

Section: Methodsmentioning

confidence: 99%

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Synthesis of novel polycyclic ring systems containing two pyrano[2,3-c]pyrazol-4-(1H)one moieties

Eller

Wimmer

Hölzer

2007

Chem Heterocycl Comp

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Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Synthesis of novel polycyclic ring systems containing two pyrano[2,3-c]pyrazol-4-(1H)one moieties

Eller

Wimmer

Hölzer

2007

Chem Heterocycl Comp

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“…This section only includes the synthesis and characterization of the molecular baskets 1 and 2 and their side products, tubelike dimeric 11 and 13; all other syntheses are reported in the Supporting Information. The naming of the compounds by the "phane nomenclature" [37] is also included in the Supporting Information.…”

Section: Methodsmentioning

confidence: 99%

Cycloalkane and Alicyclic Heterocycle Complexation by New Switchable Resorcin[4]arene‐Based Container Molecules: NMR and ITC Binding Studies

Hornung

Fankhauser

Shirtcliff

et al. 2011

Chemistry A European J

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The synthesis and structural characterization of novel, "molecular basket"-type bridged cavitands is reported. The resorcin[4]arene-based container molecules feature well-defined cavities that bind a wide variety of cycloalkanes and alicyclic heterocycles. Association constants (K(a)) of the 1:1 inclusion complexes were determined by both (1)H NMR and isothermal titration calorimetry (ITC). The obtained K(a) values in mesitylene ranged from 1.7×10(2) M(-1) for cycloheptane up to 1.7×10(7) M(-1) for morpholine. Host-guest complexation by the molecular baskets is generally driven by dispersion interactions, C-H···π interactions of the guests with the aromatic walls of the cavity, and optimal cavity filling. Correlations between NMR-based structural data and binding affinities support that the complexed heterocyclic guests undergo additional polar C-O···C=O, N-H···π, and S···π interactions. The first crystal structure of a cavitand-based molecular basket is reported, providing precise information on the geometry and volume of the inner cavity in the solid state. Molecular dynamic (MD) simulations provided information on the size and conformational preorganization of the cavity in the presence of encapsulated guests. The strongest binding of heterocyclic guests, engaging in polar interactions with the host, was observed at a cavity filling volume of 63 ± 9%.

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“…40, 41 The single crystal X ray diffraction study of 4•DMF was performed on a NONIUS B.V. CAD 4 X ray diffractometer. The crystals, C 52 H 42 N 6 O 5 •2(C 3 H 7 NO), are monoclinic; at 20 °C a = 13.028(5) Å, b = 24.559(5) Å, c = 16.374(4) Å, β = 103.28(2)°, V = 5099(3) Å 3 , d calc = 1.27 g cm -3 , Z = 4, space group P2 1 /n.…”

Section: Methodsmentioning

confidence: 99%

Synthesis, structure, and electrochemical properties of 12,42-dioxo-21,31-diphenyl-7,10,13-trioxa-1,4(3,1)-diquinoxalina-2(2,3),3(3,2)-diindolizinacyclopentadecaphane

et al. 2007

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The oxidative dehydrocyclization of the 3 (indolizin 2´ yl) 2 oxoquinoxaline monopodand performed either electrochemically or under the action of molecular iodine affords new redox active heterocyclophane consisting of the redox switchable biindolizine fragment combined with the polyether bridged π deficient quinoxaline systems. The single crystal X ray diffrac tion study showed that the trioxaundecane chain of heterocyclophane adopts an extended conformation, and one of the phenyl substituents of the molecule closes the pseudocavity formed by the spacer from one of the sides. The cyclic voltammetric study of heterocyclophane in MeCN and DMF showed the three step oxidation of the indolizine fragments accompanied by the single electron transfer in each step. The first and third steps are reversible, and the second step is irreversible. The oxidation at potentials of the first peak gives rise to stable radical cations detected by the ESR method (g = 2.0024, a 2N = 0.26 mT).In recent years, the synthesis of macrocyclic com pounds, which can reversibly respond to external actions (thermal, photochemical, electrochemical, pH, etc.) by changing important properties and characteristics (the cavity size, the surface shape, the electronic structure, the complexing ability, etc.) due to the specially introduced functional groups or fragments, has taken a special place in supramolecular chemistry. 1 Such "sensitive" hetero cyclophanes containing redox active biindolizine systems can serve as molecular switches 2 and membrane carriers 3 and are of great interest in the design of new sensors for modern technologies based on molecular processes. Un like redox active compounds (ferrocenes, 4,5 tetrathia fulvalenes, 6,7 and quaternized 4,4´ bipyridines 8,9 ), bi indolizines have found little use as active regions, which make cyclophanes able to respond to external actions, in spite of the fact that biindolizines are quite stable two step redox systems, whose electrochemical behavior has been studied in sufficient detail. 10-15Indolizines are π rich compounds, which are readily oxidized (~0.2-0.3 V relative to Fc 0/+ ) to form radical cations. 10-14 The stability and subsequent transforma tions of radical cations are determined primarily by the presence of hydrogen atoms in the pyrrole ring of the indolizine system. The radical cations and dications of 3,3´ biindolizines, in which all hydrogen atoms in the five membered ring are replaced by alkyl or aryl groups, are quite stable and can be isolated and characterized as perchlorates. 12 The electrochemical behavior of two dia stereomers of macrocyclic biindolizines, in which both heterofragments are linked at positions 3,3´ and, through a bridge, at positions 1,1´, is different. 13 Thus, the diaste reomer having the anti configuration is oxidized to form stable radical cations and dications, whereas the oxida tion of the diastereomer having the syn configuration is followed by the intramolecular cyclization with the in volvement of the C(5) and C(5´) atoms of the pyridine rings of...

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Phane nomenclature. Part II. Modification of the degree of hydrogenation and substitution derivatives of phane parent hydrides (IUPAC Recommendations 2002)

Cited by 42 publications

References 8 publications

Synthesis of novel polycyclic ring systems containing two pyrano[2,3-c]pyrazol-4-(1H)one moieties

Synthesis of novel polycyclic ring systems containing two pyrano[2,3-c]pyrazol-4-(1H)one moieties

Cycloalkane and Alicyclic Heterocycle Complexation by New Switchable Resorcin[4]arene‐Based Container Molecules: NMR and ITC Binding Studies

Synthesis, structure, and electrochemical properties of 12,42-dioxo-21,31-diphenyl-7,10,13-trioxa-1,4(3,1)-diquinoxalina-2(2,3),3(3,2)-diindolizinacyclopentadecaphane

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