Silver(I) complex of 5,6,11,12-tetradehydrodibenzo[a,e]cyclooctene

Hellbach, Björn; Röminger, Frank; Gleiter, Rolf

doi:10.1016/j.jorganchem.2005.12.068

Journal of Organometallic Chemistry

2006

DOI: 10.1016/j.jorganchem.2005.12.068

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Silver(I) complex of 5,6,11,12-tetradehydrodibenzo[a,e]cyclooctene

Björn Hellbach¹,

Frank Röminger²,

Rolf Gleiter³

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Cited by 3 publications

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“…The Sondheimer diyne (5,6,11,12-tetradehydrodibenzo[a,e]cyclooctene) (2) (Scheme 1) is a strained diyne which is straightforward to synthesise. It has been used as a monomer in Mo-catalysed ring-opening alkyne metathesis polymerization reactions 29 and to couple together Ag(I) species 30 and biomolecules. 31 For our purposes, it enables the union of twopotentially different -Pt IV azido complexes under catalyst-free conditions, without interaction of either Pt IV centre with any other functional groups on the newly formed 1,2,3-triazole ligands -something which has complicated our earlier studies.…”

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A visible-light photoactivatable di-nuclear Pt^IV triazolato azido complex

et al. 2019

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A visible-light photoactivatable di-nuclear Pt^IV triazolato azido complex

et al. 2019

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Substituted 5,6,11,12-Tetradehydrodibenzo[a,e]cyclooctenes: Syntheses, Properties, and DFT Studies of Substituted Sondheimer–Wong Diynes

Peng

Shinohara

et al. 2014

J. Org. Chem.

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Highly strained cyclic acetylenes 5,6,11,12-tetradehydrodibenzo[a,e]cyclooctenes (Sondheimer-Wong diynes) having various substituents on their benzene rings were synthesized successfully by one-pot treatment of the corresponding formyl sulfones with diethyl chlorophosphate/lithium hexamethyldisilazide (LiHMDS) and then lithium diisopropylamide (LDA). When mixtures of two types of formyl sulfones bearing different substituents were subjected to this protocol, the unsymmetrically substituted Sondheimer-Wong diynes could be synthesized in a stepwise manner by isolation of the heterocoupled vinyl sulfone intermediates followed by their treatment with LDA. The UV-vis absorption spectra and cyclic voltammograms of the substituted Sondheimer-Wong diynes were recorded. The electronic effect of substituents on the diynes was investigated in their click reactions and nucleophilic and electrophilic additions.

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Synthesis and Properties of Oligo[n]cruciforms: Nanosized Sterically Encumbered Tetraethynylphenyl-Homologated Fluorophores

et al. 2009

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A series of nanosized phenyleneethynylenes have been prepared which are sterically insulated from the surrounding environment by multiple functionalization with triisopropylsilyl (TIPS) substituents. The phenyleneethynylenes comprise oligo[n]cruciforms 1-4 (n = 3-5) and a dehydrotribenzo[12]annulene 5, the former of which possess para-acyclic and the latter ortho-cyclic electronic conjugation pathways. All compounds were characterized by (1)H and (13)C NMR, IR, and mass spectroscopic techniques. The X-ray crystal structure of 1 confirmed the sterically isolating properties of the TIPS substituents. A comparison of the physical properties of these electronically differing systems revealed that they were all luminescent upon UV irradiation displayed negligible aggregation in dilute solution and that particular members of the series studied were electrochemically active, undergoing facile reversible reductions. The phenyleneethynylenes also exhibited significantly enhanced thermal stability by virtue of the presence of the TIPS substituents. The properties of 1-5 suggest that they are promising building blocks for the construction of materials for novel molecular electronics applications.

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Silver(I) complex of 5,6,11,12-tetradehydrodibenzo[a,e]cyclooctene

Cited by 3 publications

References 13 publications

A visible-light photoactivatable di-nuclear Pt^IV triazolato azido complex

A visible-light photoactivatable di-nuclear Pt^IV triazolato azido complex

Substituted 5,6,11,12-Tetradehydrodibenzo[a,e]cyclooctenes: Syntheses, Properties, and DFT Studies of Substituted Sondheimer–Wong Diynes

Synthesis and Properties of Oligo[n]cruciforms: Nanosized Sterically Encumbered Tetraethynylphenyl-Homologated Fluorophores

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Silver(I) complex of 5,6,11,12-tetradehydrodibenzo[a,e]cyclooctene

Cited by 3 publications

References 13 publications

A visible-light photoactivatable di-nuclear PtIV triazolato azido complex

A visible-light photoactivatable di-nuclear PtIV triazolato azido complex

Substituted 5,6,11,12-Tetradehydrodibenzo[a,e]cyclooctenes: Syntheses, Properties, and DFT Studies of Substituted Sondheimer–Wong Diynes

Synthesis and Properties of Oligo[n]cruciforms: Nanosized Sterically Encumbered Tetraethynylphenyl-Homologated Fluorophores

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Product

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A visible-light photoactivatable di-nuclear Pt^IV triazolato azido complex

A visible-light photoactivatable di-nuclear Pt^IV triazolato azido complex