The synthesis of bromo and iodo trifunctionalised tribenzosilatranes

Alvarez, R; Mehl, Georg H.

doi:10.1016/j.tetlet.2004.11.034

Cited by 6 publications

(7 citation statements)

References 12 publications

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“…Tris(4-bromo-2-methoxyphenyl)amine was obtained as described in ref. 27. 2-[5 0 -(2-methyl-1,3-dioxolan-2-yl)-2,2 0bithien-5-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (2) was obtained as described previously.…”

Section: Methodsmentioning

confidence: 99%

A star-shaped D–π–A small molecule based on a tris(2-methoxyphenyl)amine core for highly efficient solution-processed organic solar cells

et al. 2014

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Section: Methodsmentioning

confidence: 99%

A star-shaped D–π–A small molecule based on a tris(2-methoxyphenyl)amine core for highly efficient solution-processed organic solar cells

et al. 2014

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“…Because the high electron-donating ability of the methoxy group should strongly perturb the electrophilic bromination, conversion of 1 to the moderately activated arene 2 was performed, which enabled easy and regioselective access to 3 by trisbromination. 33,35 Iodination was revealed to be more problematic: TPA 2 in the presence of the widely used reagents Ag 2 SO 4 /I 2 , 36 I 2 /In(OTf), 37 AgOTf/I 2 , 38 or R 4 N + , ICl 2salt 39 either reacts extremely slowly or leads to intractable mixtures. Finally a HgO/iodine mixture 40 leads to clean conversion of 2 into 4 within 3 days.…”

Section: Resultsmentioning

confidence: 99%

Synthetic Strategies to Derivatizable Triphenylamines Displaying High Two-Photon Absorption

et al. 2008

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A versatile synthetic strategy to access a set of highly fluorescent pi-conjugated triphenylamines bearing a functional linker at various positions on one phenyl ring is described. These compounds were designed for large two-photon absorption (2PA) and in particular for labeling of biomolecules. The monoderivatized trisformylated or trisiodinated intermediates described herein allow introduction of a large variety of electron-withdrawing groups required for large 2PA as well as a panel of chemical functions suitable for coupling to biomolecules. The monoderivatized three-branched compounds and in particular the benzothiazole (TP-3Bz) series show remarkable linear (high extinction coefficients and high quantum yield) and nonlinear (high 2-photon cross sections) optical properties. Interestingly the presence of functional side chains does not disturb the two-photon absorption. Finally, monoderivatized two-branched derivatives also appear to be valuable candidates. Altogether the good optical properties of the new derivatizable pi-conjugated TPA combined with their small size and their compatibility with bioconjugation protocols suggest that they represent a new chemical class of labels potentially applicable for the tracking of biomolecules using two-photon scanning microscopy.

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“…Tris(4-bromo-2-methoxyphenyl)amine was obtained as described in ref. 40. All reactions, unless stated otherwise, were carried out under an inert atmosphere.…”

Section: Methodsmentioning

confidence: 99%

Star-shaped D–π–A oligothiophenes with a tris(2-methoxyphenyl)amine core and alkyldicyanovinyl groups: synthesis and physical and photovoltaic properties

et al. 2016

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Synthesis of a series of star-shaped oligomers having a novel electron donating tris(2-methoxyphenyl)-amine (m-TPA) core, which is linked through a bithiophene or terthiophene p-bridge with electrondeficient alkyldicyanovinyl (alkyl-DCV) groups, is described. A comprehensive study of the oligomers revealed significant dependence of their physical properties, including absorption, molecular frontier energy levels, crystal packing, and melting and glass transition temperatures, upon the chemical structure. A comparison of their photophysical properties to the nearest analog having the common dicyanovinyl (DCV) groups demonstrated a number of benefits to use alkyl-DCV units for the design of donor-acceptor small molecules: higher solubility, increased electrochemical stability, better photovoltaic performance, and possibility to control the relative physical and photovoltaic properties by a simple adjustment of alkyl and p-bridge lengths. Modification of the well-known triphenylamine (TPA) core in the star-shaped oligomers by methoxy groups increases not only solubility, but also crystallinity of the oligomers, whereas their photovoltaic performance stays on a similar level as their analogs with a TPA core. The study demonstrates that these design strategies represent interesting and simple tools for the effective modulation of properties of star-shaped molecules.

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The synthesis of bromo and iodo trifunctionalised tribenzosilatranes

Cited by 6 publications

References 12 publications

A star-shaped D–π–A small molecule based on a tris(2-methoxyphenyl)amine core for highly efficient solution-processed organic solar cells

A star-shaped D–π–A small molecule based on a tris(2-methoxyphenyl)amine core for highly efficient solution-processed organic solar cells

Synthetic Strategies to Derivatizable Triphenylamines Displaying High Two-Photon Absorption

Star-shaped D–π–A oligothiophenes with a tris(2-methoxyphenyl)amine core and alkyldicyanovinyl groups: synthesis and physical and photovoltaic properties

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