Synthese und struktur von [2.2](2,7)pyrenophan

Irngartinger, Hermann; Kirrstetter, R. G. H.; Krieger, Claus; Rodewald, H.; Staab, Heinz A.

doi:10.1016/s0040-4039(01)93063-1

Cited by 40 publications

(17 citation statements)

References 8 publications

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“…The molecular structure of (I) has been reported by Irngartinger, Kirrstetter, Krieger, Rodenwald & Staab (1977) in the course of our X-ray studies on (I). A comparison of the molecular structures of (I) and (II) is made in this paper.…”

Section: Introductionmentioning

confidence: 76%

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Structural chemistry of layered cyclophanes. III. Molecular structures of [2.2](2,7)pyrenophane-1,1'-diene and pyrene (redetermined) at –160°C

Yan¹,

Hama²,

Yasuoka³

et al. 1978

Acta Crystallogr B Struct Sci

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The molecular structure of [2.2](2,7)pyrenophane-l,l'-diene was determined from X-ray diffraction data collected on a four-circle diffractometer at -160 o C. Crystals belong to the monoclinic space group P2 ffc with two molecules per unit cell; a = 9.829 (2), b = 12.631 (2), c = 10.001 (2) A and fl = 113.82 (1) °. The structure was solved by the direct method and refined by block-diagonal least squares to an R of 0.064 for 2917 observed reflexions. The pyrene moieties have shallow-boat conformations connected by ethylenic bridges of length 1.344 (3) A and with angles of 118.5 (2) and 119.3 (2) °. The molecular structure ofpyrene was redetermined to compare its structure with that of [2.2](2,7)pyrenophane-l,l'-diene. The X-ray data were measured at -160 °C to obtain standard data of high accuracy for the condensed aromatic compounds. The final R value was 0-063 for 2361 observed reflexions. Good agreement was observed between the chemically equivalent parts of the molecule.

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Section: Introductionmentioning

confidence: 76%

“…which the other pyrene moiety overlaps and two longer ones lie out of the range of its overlapping. The mean structure of (I) (Irngartinger et al, 1977) is also listed in Table 13. A remarkable feature is that in contrast to the present work a shortfbond is observed.…”

Section: F X-ray Neutron Mo A(n-x)*mentioning

confidence: 99%

Structural chemistry of layered cyclophanes. III. Molecular structures of [2.2](2,7)pyrenophane-1,1'-diene and pyrene (redetermined) at –160°C

Yan¹,

Hama²,

Yasuoka³

et al. 1978

Acta Crystallogr B Struct Sci

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“…57 The pyrenophanes 30, 68 and 70 form an interesting series, in which the two pyrene systems are increasingly bent, albeit not over a particularly large range (θ = 0°, 19.0° and 37.9° for 70, 68 and 30, respectively). 52,56,58,59 In the absorption spectra of these three compounds, the shortening of the bridges is accompanied by a red shift and loss of vibronic fine structure of the lowest energy bands, which was explained as being due to increasing interactions between the two pi systems as they are forced closer to one another. All three pyrenophanes exhibit pure excimer fluorescence (λ max = 556, 515, 469 nm for 30, 68 and 70, respectively) with Stokes shifts close to that of pyrene (5050 cm -1 ).…”

Section: Figurementioning

confidence: 99%

“…two-decade period starting in the mid 1970s, feature a pyrene system that is held in a face-to-face orientation with respect to either a second pyrene system or a different aromatic system of similar size. 33,35,[52][53][54][55][56][57] The only notable departure from the standard Type I cyclophane chemistry was with the synthesis of 71 and 72. 57 The pyrenophanes 30, 68 and 70 form an interesting series, in which the two pyrene systems are increasingly bent, albeit not over a particularly large range (θ = 0°, 19.0° and 37.9° for 70, 68 and 30, respectively).…”

Section: Figurementioning

confidence: 99%

Cyclophanes containing large polycyclic aromatic hydrocarbons

2015

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Cyclophanes have been firmly entrenched as a distinct class of compounds for well over half a century. The two main factors that have kept this field of chemistry going so strongly for such a long time are tremendous structural diversity and the interesting behaviour that is often observed. Although a very large number cyclophanes has been reported, only a very small proportion of them contain polycyclic aromatic systems that can be thought of as "large", i.e. with ≥4 rings. This Review puts the spotlight on such cyclophanes, illuminating both the chemistry that was used to synthesize them and what was learned from studying them. Context for the main body is provided by the careful consideration of the anatomy of a cyclophane and the classification of general synthetic approaches. The subsequent sections cover eleven different PAHs and are organized primarily according to increasing size of the aromatic system, starting with pyrene (C16, the only large polycyclic aromatic system to have been incorporated into numerous cyclophanes) and ending with hexabenzo[bc,ef,hi,kl,no,qr]coronene (C42).

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“…Single-crystal X-ray crystallographic analysis of this compound provides the most precise measure to date of the vdW distance between two undistorted AA-stacked graphene fragments. Previously described bilayer molecules with shorter or contorted spacers have aromatic planes that are bent or rotated with respect to each other, [28][29][30][31][32][33][34] and structures with longer spacers relax into ABstacked arrangements that are typical for intermolecular contacts between PAHs. 29,30,[35][36][37][38] We deposited a cyclophane onto a ferromagnetic metal surface, nanoscale Co(111) islands, and onto non-magnetic Cu(111).…”

Section: Introductionmentioning

confidence: 99%