Perchlorbutatrien und Perchlor‐[4]radialen

Heinrich, Burkhard; Roedig, Alfred

doi:10.1002/ange.19680800918

Cited by 27 publications

(4 citation statements)

References 9 publications

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“…(2) A 'puckered' structure which has the CCI, groups alternately above and below the equatorial plane (D,,). If one were starting with no prior knowledge of the structure, the following possibilities would have to be considered: (1) a planar symmetrical structure ( D 4 J .…”

Section: Discussionmentioning

confidence: 99%

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The infrared and Raman spectra of perchloro‐[4] ‐ radialene

Finseth

Miller

1976

J Raman Spectroscopy

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Infrared and Raman spectra are reported for polycrystalline perchloro-[4]-radialene and for solutions in cc1.1 and CSz. An earlier X-ray structure determination by van Remoortere and Boer has shown that in the crystal the molecular symmetry is almost Dzd (puckered ring), but is slightly distorted to CZ. This distortion was attributed to crystal packing forces. The vibrational spectrum does not show the distortion. The spectra are essentially the same for polycrystalline solid as for solution, and are completely compatible with D z~ in both states. Assignments are made for a few of the modes where evidence warrants it. Some observations are also made about the mass spectrum, which has a rich structure because of the many isotopic species.

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Section: Discussionmentioning

confidence: 99%

“…The sample was graciously provided by Prof. Dr A. Roedig of the Institut fur Organische Chemie der Universitat Wurzburg, who reported the original preparation [ 2 ] . It was in the form of coarse, needle-like white crystals which melted at 162-3 "C, and was used without further purification.…”

Section: Methodsmentioning

confidence: 99%

The infrared and Raman spectra of perchloro‐[4] ‐ radialene

Finseth

Miller

1976

J Raman Spectroscopy

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“…Tetraiodobutatriene is extremely unstable in solution, 66 tetrafluorobutatriene ((5), chart 1.3), the only gas in this series, is known to explode violently when exposed to air or warmed above its boiling point of -5°C. 67 Tetrabromobutatriene and tetrachlorobutatriene 68 While the chemistry of tetrafluoroallene has been studied extensively 69,70 and its longer homologue 5 has been synthesized and characterized by IR-and 19 F-NMRspectroscopy by Martin and Sharkey as early as 1959, the chemistry of 5 remained almost unexplored due to the compound´s extreme instability. 67 It even polymerizes at -85°C within a short time.…”

Section: The Capability Of Cumulenes For Different Binding Modes To Mmentioning

confidence: 99%

“…Attempts to prevent this undirected polymerization (as shown in scheme 2. 68,104,105 and the all-phenyl triene 106 a head-to-head type dimer. 107 For the latter the radialene type dimer is also known but not from dimerization, but from an unusual cyclization of an ate-type complex of a copper carbenoid derived from 1,1-dibromo-2,2-diphenylethylene.…”

Section: Tetrafluorobutatriene -Dimersmentioning

confidence: 99%

Fluorinated butatrienes

Ehm¹,

Akkerman²,

Lentz³

2010

Journal of Fluorine Chemistry

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Highly Functionalized Dimeric Tetraethynylethenes and Expanded Radialenes: Strong Evidence for Macrocyclic Cross-Conjugation

et al. 2001

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A selection of dimeric tetraethynylethenes (TEEs) and perethynylated expanded radialenes, containing different donor/acceptor substitution patterns, have been prepared and fully characterized. The first X-ray crystal structure of an expanded [6]radialene, with twelve peripheral 3,5-di(tert-butyl)phenyl substituents, is presented. This macrocycle, the all-carbon core of which is isomeric with fullerene C60, adopts a non-planar, "chair-like" conformation. Also a TEE dimer, carrying N,N-dimethylaniline donor substituents, has been subjected to an X-ray crystallographic analysis. The electronic properties were studied by UV/Vis spectroscopy and electrochemistry, providing fundamental insight into mechanisms of pi-electron delocalization in the acyclic and macrocyclic chromophores. Donor or donor-acceptor-substituted dimeric TEE derivatives show very strong absorptions extending over the entire UV/Vis region; their longest wavelength absorption bands have high charge-transfer character. Macrocyclic cross-conjugation in the expanded radialenes becomes increasingly efficient with increasing donor-acceptor polarization. A dual, strongly solvent-polarity-dependent fluorescence was observed for a tetrakis(N,N-dimethylaniline)-substituted dimeric TEE; this interesting emission behavior is explained by the twisted intramolecular charge-transfer (TICT) state model. Donor-substituted expanded radialenes display huge resonance-enhanced third-order nonlinear optical coefficients.

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Perchlorbutatrien und Perchlor‐[4]radialen

Cited by 27 publications

References 9 publications

The infrared and Raman spectra of perchloro‐[4] ‐ radialene

The infrared and Raman spectra of perchloro‐[4] ‐ radialene

Fluorinated butatrienes

Highly Functionalized Dimeric Tetraethynylethenes and Expanded Radialenes: Strong Evidence for Macrocyclic Cross-Conjugation

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