2,3,9,10‐Tetrakis(trimethylsilyl)[5]phenylene. Synthesis via Regiospecific Cobalt‐Catalyzed Cocyclization of 1,6‐Bis(triisopropylsilyl)‐l,3,5‐hexatriyne

Blanco, Luis; Helson, Harold E.; Hirthammer, Michael; Mestdagh, H.; Spyroudis, Spyros; Vollhardt, K. Peter C.

doi:10.1002/anie.198712461

Cited by 52 publications

(21 citation statements)

References 7 publications

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“…900 ns for (1). The influence of temperature on τ F was investigated for angular [3]phenylene (3a) and for triangular [4]phenylene (4). In comparison to those obtained at room temperature, the fluorescence lifetimes in MeTHF at 77 K approximately doubled to τ F = 40 ns and 145 ns for (3a) and (4), repectively.…”

Section: Figmentioning

confidence: 98%

“…Fluorescence excitation and emission spectra of triangular [4]phenylene (4) in MeTHF at 77 K. Inset: logarithmic singlet absorption spectrum at 298 K in THF.…”

Section: Figmentioning

confidence: 99%

“…Triplet absorption spectra of angular [3]phenylene(3a), zig-zag [4]phenylene (3b) and zig-zag [5]phenylene (3c) in THF at 298 K. …”

Section: Figmentioning

confidence: 99%

“…[21][22][23] As to the photophysical behaviour of the two [3]phenylenes, Niemeyer has revealed striking differences (in cyclohexane at room temperature): Whereas linear [3]phenylene (2a) was found to be non-fluorescent (Φ F < 10 -5 ), angular [3] 28 X-ray structure analysis data show also a strong alternance of the C-Cbond length in the central rings of the zig-zag [N]phenylenes. 5,29 In the present work, photophysical investigations of the linear and angular [3]phenylenes (2a), (3a), the zig-zag [4]-and [5]phenylenes (3b), (3c), and the triangular [4]phenylene (4) were performed (Fig. 1).…”

Section: Introductionmentioning

confidence: 98%

“…[N]phenylenes (3), and, e. g., the branched triangular [4]phenylene (4), which has also been named starphenylene (cf. Biphenylene (1), first synthesized in 1941, 6 is a representative alternant, anti-aromatic molecule.…”

Section: Introductionmentioning

confidence: 99%

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Photophysical properties of [N]phenylenes

Dosche

Löhmannsröben

Bieser

et al. 2002

Phys. Chem. Chem. Phys.

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In the present study, photophysical properties of [N]phenylenes were studied by means of stationary and time-resolved absorption and fluorescence spectroscopy (in THF at room temperature). For biphenylene (1) and linear (1) and (2a) as "fast IC compounds", with k IC > 10 9 s -1 , and of (3) and (4) as "slow IC compounds", with k IC ≈ 10 7 s -1 , is suggested. This classification cannot simply be related to Hückel's rule-type concepts of aromaticity, because the group of "fast IC compounds" consists of "antiaromatic" (1) and "aromatic" (2a), and the group of "slow IC compounds" consists of "antiaromatic" (3b), (4) and "aromatic" (3a), (3c). The IC in the[N]phenylenes is discussed within the framework of the so-called energy gap law established for non-radiative processes in benzenoid hydrocarbons.2

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Section: Figmentioning

confidence: 98%

“…Fluorescence excitation and emission spectra of triangular [4]phenylene (4) in MeTHF at 77 K. Inset: logarithmic singlet absorption spectrum at 298 K in THF.…”

Section: Figmentioning

confidence: 99%

“…Triplet absorption spectra of angular [3]phenylene(3a), zig-zag [4]phenylene (3b) and zig-zag [5]phenylene (3c) in THF at 298 K. …”

Section: Figmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 98%

Section: Introductionmentioning

confidence: 99%

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Photophysical properties of [N]phenylenes

Dosche

Löhmannsröben

Bieser

et al. 2002

Phys. Chem. Chem. Phys.

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(2-Bromoethynyl)tris(1-methylethyl)silane

Chatani

2014

Encyclopedia of Reagents for Organic Synthesis

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Cotrimerizations of Acetylenic Compounds

et al. 2007

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The cyclotrimerization of acetylenic compounds is a useful method for the construction of three new bonds in a one‐step process. Although symmetry‐allowed, there is a paucity of examples of purely thermal [2+2+2] cycloadditions. The first example reported was in 1866, which was the cyclization of acetylene to benzene. High temperatures are required for this reaction and a mixture of products is formed. In 1948, Reppe discovered the first transition‐metal catalyzed version of this reaction in which nickel was used and substituted benzenes were formed. Since then catalysts based on transition metals, lanthanides, actinide, and aluminum have been developed for the cycloaddition of substituted alkynes to benzene derivatives. Many compounds can take part in the cyclization reactions to give four‐, five‐,six, or eight membered rings. Many of these reactions have found many applications in organic synthesis This chapter is devoted to early to late transition metal‐mediated cotrimerization of acetylenic compounds directed towards organic synthesis. It addresses the scope and generality of the reaction, as well as the current state of the art, with regard to region‐and stereoselectivities. In the context of selectivity, a mechanistic overview is provided. Inter‐and intramolecular versions of the cyclizations are presented with an emphasis on applications in synthesis. The literature up to mid‐2004 is covered.

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2,3,9,10‐Tetrakis(trimethylsilyl)[5]phenylene. Synthesis via Regiospecific Cobalt‐Catalyzed Cocyclization of 1,6‐Bis(triisopropylsilyl)‐l,3,5‐hexatriyne

Cited by 52 publications

References 7 publications

Photophysical properties of [N]phenylenes

Photophysical properties of [N]phenylenes

(2-Bromoethynyl)tris(1-methylethyl)silane

Cotrimerizations of Acetylenic Compounds

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