Total control on the synthesis of regio and stereoisomers of vinylic tellurides

Dabdoub, Miguel J.; Cassol, Tânia M.

doi:10.1016/0040-4020(95)00840-5

Cited by 30 publications

(17 citation statements)

References 38 publications

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“…6a was easily prepared by modifying a previously reported procedure (Supplementary Notes 2 , 3 , and 4 and Supplementary Figs. 19 and 20 ) 38 , 39 and copolymerized with methyl acrylate (MA, 500 equivalents (equiv.)) in the presence of organotellurium CTA 9 12 at different [ 6a ]/[ 9 ] ratios of 3, 7, 15, 31, and 63 in the presence of azobisisobutyronitrile (AIBN) (0.2 equiv.)…”

Section: Resultsmentioning

confidence: 99%

Synthesis of structurally controlled hyperbranched polymers using a monomer having hierarchical reactivity

Nemoto

Tosaka

et al. 2017

Nat Commun

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Hyperbranched polymers (HBPs) have attracted significant attention because of their characteristic topological structure associated with their unique physical properties compared with those of the corresponding linear polymers. Dendrimers are the most structurally controlled HBPs, but the necessity of a stepwise synthesis significantly limits their applications in materials science. Several methods have been developed to synthesize HBPs by a one-step procedure, as exemplified by the use of AB2 monomers and AB′ inimers under condensation and self-condensing vinyl polymerization conditions. However, none of these methods provides structurally controlled HBPs over the three-dimensional (3D) structure, i.e., molecular weight, dispersity, number of branching points, branching density, and chain-end functionalities, except under special conditions. Here, we introduce a monomer design concept involving two functional groups with hierarchical reactivity and demonstrate the controlled synthesis of dendritic HBPs over the 3D structure by the copolymerization of the designed monomer and acrylates under living radical polymerization conditions.

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Section: Resultsmentioning

confidence: 99%

Synthesis of structurally controlled hyperbranched polymers using a monomer having hierarchical reactivity

Nemoto

Tosaka

et al. 2017

Nat Commun

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“…The key precursor in the synthesis of 3a is enyne 5a, from which the dibenzobarrelene skeleton is constructed by an intramolecular [4+2] cycloaddition reaction. Enyne 5a was obtained by nucleophilic substitution of 1-lithiobut-1-en-3-yne 6, generated by treatment of (butyltelluro)butenyne 7 with butyllithium in THF at -78°C, [19,20] with 9-(chloromethyl)anthracene (8a). Subsequently, enyne 5a was heated at 60°C in THF to furnish the desired 3a in 40 % yield (Scheme 1).…”

Section: Synthesis and Structure Elucidationmentioning

confidence: 99%

Synthesis and Photophysical Properties of Dibenzobarrelene‐Incorporated 1,4‐Diphenyl‐1,3‐pentadienes and a 5‐Sila Derivative Having High Fluorescence Efficiency

et al. 2018

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Two dibenzobarrelene‐incorporated 1,3‐pentadienes and a 5‐sila derivative have been synthesized by intramolecular cycloaddition reactions between (9‐anthryl)methyl, (9‐anthryl)hydroxymethyl, or (9‐anthryl)dimethylsilyl groups and a phenylethynyl group linked by an ethene moiety with a cis conformation. The three compounds exhibit blue luminescence (λem = 432–445 nm) in CH2Cl2 with high quantum yields (ΦF = 0.83–0.92). In the solid state, the methylene and dimethylsilyl derivatives luminesce (λem = 442 and 438 nm, respectively) with narrow full‐width at half‐maxima (FWHM, 40 and 37 nm, respectively), whereas the hydroxymethylene compound shows a broad and slightly redshifted emission (λem = 488 nm, FWHM = 112 nm) due to intermolecular hydrogen bonding. The fluorescence intensity of the dimethylsilyl compound was decreased by desilylation with Bu4NF. The structures of the compounds were characterized unambiguously by NMR spectroscopy and X‐ray crystallography, and their photophysical properties were elucidated both experimentally as well as by TD‐DFT calculations.

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“…Butyltelluroalkynes are important intermediates in organic synthesis, since they permit the stereospecific synthesis of vinylic tellurium species (Comasseto et al, 1997), which in turn are precursors of other vinyl metal derivatives such as vinyl lithium, copper, zinc, magnesium, sodium and calcium. In previous papers, we reported the synthesis ) and reactions Dabdoub & Cassol, 1995) of these acetylenic tellurium species. Reaction of acetylenic tellurides with Br or I produces organyltellurium trihalides and the corresponding 1,1,2-trihaloethylenes, instead of the expected diorganyl tellurium dihalides (Dabdoub et al, 1990).…”

Section: Commentmentioning

confidence: 99%