223799-09-5

Upstream product

• 6311-60-0 3,5-dibromonitrobenzene 
• 13154-24-0 triisopropylsilyl chloride 
• 7567-63-7 1,3,5-Triethynylbenzene 
• 144001-09-2 (5-bromo-1,3-phenylene)bis(ethyne-2,1-diyl)bis(trimethylsilane) 
• 149428-64-8 1-bromo-3,5-diiodobenzene 
• 626-39-1 1,3,5-trisbromobenzene 
• 1275593-71-9 C₂₇H₃₈O₂Si 
• 144000-99-7 1-bromo-3,5-bis(3'-hydroxy-3'-methylbut-1'-ynyl)benzene 
• 827-94-1 2,6-dibromo-4-nitroaniline 
• 626-40-4 3,5-dibromoaniline 
• 223799-07-3 1,3-dibromo-5-(triisopropylsilylethynyl)benzene 
• 89343-06-6 tris-iso-propylsilyl acetylene 
• 19752-57-9 1,3-dibromo-5-iodobenzene 
• 223799-08-4 1-(triisopropylsilylethynyl)-3,5-bis(trimethylsilylethynyl)benzene 

Downstream Products

• 346671-37-2 1,3-[Cl(Et₃P)2PdCC]2-5-[(i-Pr)3SiC₂]C₆H₃ 
• 223799-10-8 [(C₃H₇)3SiCCC₆H₃(CCPt(P(C₂H₅)3)2CCC₆H₄OCH₃)2] 
• 1275593-73-1 C₄₉H₆₈N₆Si 
• 1275593-68-4 4,4'-(5-ethynyl-1,3-phenylene)bis(1-(3,5-di-tert-butylphenyl)-1H-1,2,3-triazole) 
• 1275593-61-7 2-(1-(4-(4-(3,5-bis(1-(3,5-di-tert-butylphenyl)-1H-1,2,3-triazol-4-yl)phenyl)-1H-1,2,3-triazol-1-yl)phenyl)-1H-1,2,3-triazol-4-yl)-5-((triisopropylsilyl)ethynyl)pyridine 
• 1404213-47-3 C₇₇H₈₂O₂Si 
• 1442467-01-7 1,3-bis(4',5',8'-triphenylocta-3',5'-diene-1′-ynyl-7′-yne)-5-ethynylbenzene 
• 1442467-00-6 C₇₃H₆₆Si₃ 
• 1403834-95-6 C₅₃H₆₆Si₅ 
• 1403834-94-5 C₈₁H₁₁₆N₂O₁₆Si 

Relevant academic research and scientific papers

New conjugated molecules with two and three dithienyldiketopyrrolopyrrole (DPP) moieties substituted at meta positions of benzene toward p- and n-type organic photovoltaic materials

Two conjugated molecules, TADPP3 and TADPP2-TT, are reported, in which three and two dithienyldiketopyrrolopyrrole (DPP) moieties, respectively, are substituted at the meta positions of benzene. Based on cyclic voltammetry and absorption data, TADPP3 and TADPP2-TT possess similar HOMO and LUMO energies of about -5.2 and -3.4 eV, respectively. Thin films of TADPP3 and TADPP2-TT exhibit p-type semiconducting behavior with hole mobilities of 2.36×10 -3 and 3.76×10-4 cm2 V-1 s-1 after thermal annealing. Molecules TADPP3 and TADPP2-TT were utilized as p-type photovoltaic materials to fabricate organic solar cells after blending with phenyl C71 butyric acid methyl ester (PC 71BM) and phenyl C61 butyric acid methyl ester (PC 61BM). The relatively low JSC and fill factor values can be attributed to poor film morphologies based on AFM and XRD studies. A solar cell with a thin film of TADPP3 with PC71BM in a weight ratio of 1:2 exhibits a high open-circuit voltage (VOC) of 0.99 V and a power conversion efficiency (PCE) of 2.47 %. Interestingly, TADPP3 can also be employed as an n-type photovoltaic material. The blended thin film of TADPP3 with P3HT in a weight ratio of 1:2 gave a high VOC of 1.11 V and a PCE of 1.08 % after thermal annealing. Star-shaped small molecules: Two conjugated molecules, TADPP3 and TADPP2-TT, have been developed and applied in solution-processed organic solar cells. Molecule TADPP3 can be applied as both a donor and an acceptor. The resulting solar cells have a high open-circuit voltage (>0.9 V) and the power conversion efficiency reaches 2.47 %.

Modular syntheses of star-shaped pyridine, bipyridine, and terpyridine derivatives by employing sonogashira reactions

A simple and flexible synthesis for a series of star-shaped pyridine, bipyridine, and terpyridine derivatives is reported by using a modular approach that combines the use of a ligand, spacer, and core unit. A fairly efficient method to prepare 4′-nonafloxy-functionalized terpyridine derivatives is described. The building blocks that contain the functionalized pyridine, bipyridine, or terpyridine derivatives were linked to different C3-symmetrical core units. In most cases, Sonogashira reactions were employed in the crucial final steps of the synthesis. A star-shaped dodecafluorinated compound was also prepared in a straightforward fashion. A simple procedure for the preparation of partially silylated 1,3,5-triethynylbenzene derivatives is presented, which provides an approach to C2-symmetrical star-shaped compounds that have only one terpyridine and two terphenyl units as "dummy" ligands. The absorption and emission spectra of the fully conjugated C3-symmetrical pyridine derivatives were systematically investigated, and fairly large Stokes shifts were observed.

Synthesis of conjugated aryleneethynylenesiloles dendron

Three routes were designed to synthesize a π-conjugated aryleneethynylenesiloles dendron. With the desilylation of the disilole mono(silylethynyl) derivative in the presence of potassium carbonate (K 2CO3), the silole-containing oligomer has been successfully synthesized without impact on the Si-(CH3)2 group. The disilole mono(silylethynyl) derivative was prepared by means of the Sonogashira heterocoupling reaction between the diacetylene compound and asymmetrical silole, catalyzed by the dichloro bis(triphenylphosphine)palladium, in a divergent synthesis. Due to their steric effect and triethynylbenzene self-coupling Glaser reaction, the endeavour to prepare the dendron by controlling the molar ratio of asymmetrical silole and 1,3,5-triethynylbenzene was failed. The another attempt to prepare the dendron by different desilylation condition of triisopropylsilyl group and trimethylsilyl group was also failed, the desilylation of Si-(CH3)2 group in silacyclopentadiene unit was also easily accomplished in the presence of tetrabutylammonium fluoride(Bu4NF), whereas no reaction occurred when K 2CO3 was used instead of Bu4NF. Copyright

Studies toward the synthesis of phenylacetylene macrocycle based rotaxane precursors as building blocks for organic nanotubes

Synthetic efforts toward the preparation of rotaxane precursors based on phenylacetylene macrocycles (PAM) are described. The aim of this study was to determine the optimal structural parameters to prepare high-molecular-weight rotaxane precursors through a strategy involving two Sonogashira couplings to attach bulky blockers on the PAM core. PAMs with different sizes and functions were prepared and coupled to different blockers to assess whether or not the resulting structure adopts a rotaxane-like conformation in which the rigid rod forms after the Sonogashira coupling threads through the PAM. Copyright

Conjugated polyelectrolyte dendrimers: Aggregation, photophysics, and amplified quenching

Conjugated polyelectrolyte dendrimers (CPDs) are monodisperse macromolecules that feature a fully π-conjugated dendrimer core surrounded on the periphery by ionic solubilizing groups. CPDs are soluble in water and polar organic solvents, and they exhibit photophysics characteristic of the π-conjugated chromophores comprising the dendrimer core. Here we describe the synthesis and photophysical characterization of series of three generations of CPDs based on a phenylene ethynylene repeat unit structure that is surrounded by an array of anionic sodium carboxylate groups. Molecular dynamics simulations indicate that the first-generation CPD is flat while the second- and third-generation CPDs adopt oblate structures. Photophysical studies, including absorption, fluorescence spectroscopy, and lifetimes, show that the ester protected precursor dendrimers exhibit highly efficient blue fluorescence in THF solution emanating from the phenylene ethynylene chromophore that is in the dendrimer core. By contrast, the water-soluble CPDs have much lower fluorescence quantum yields and the absorption and fluorescence spectra exhibit features of strong chromophore-chromophore interactions. The results are interpreted as suggesting that the CPDs exist as dimer or multimer aggregates, even in very dilute solution. Fluorescence quenching of the anionic CPDs with the dication electron acceptor N,N′-dimethylviologen (MV2+) is very efficient, with Stern-Volmer quenching constants (KSV) increasing with generation number. The third-generation CPD exhibits highly efficient amplified quenching, with KSV ～ 5 × 106 M -1.

Triazole-pyridine ligands: A novel approach to chromophoric iridium arrays

We describe a novel modular approach to a series of luminescent iridium complexes bearing triazole-pyridine-derived ligands that were conveniently prepared by using "click" chemistry. One, two or three triazole-pyridine units were effectively built into the heteroaromatic macromolecule using versatile acetylene- and azide-functionalised precursors. Using this approach, a series of iridium-derived molecules, that differ in the number of iridium centres, the structural characteristics of the cyclometalating ligand and the backbone, were synthesised. The preliminary photophysical properties of the prepared complexes indicate that there is only limited interaction (through space or through the backbone) between the iridium centres within one molecule and that each iridium centre retains its individual properties. The results show that our approach can be generally applied towards covalently linked multichromophoric systems with potential application, for instance, in the design and preparation of tunable light emitters. As a demonstration of this concept, a single molecule white-light emitter, constructed from two iridium centres (yellow emission) and a fluorene unit (blue emission), is presented. The Royal Society of Chemistry.

Convergent synthesis of platinum-acetylide dendrimers

An efficient convergent route to the main chain type of organometallic dendrimers, in which platinum moieties are linked by 1,3,5-triethynylbenzene, has been developed. The synthesis of platinum-acetylide dendrons involved the use of two types of trialkylsilyl groups for protection of the terminal acetylene. The platinum-acetylide dendrimers were prepared up to the third generation by reacting dendrons with a triplatinum core and a tetraplatinum core. Spectroscopic characterization and trace experiments by gel permeation chromatography indicated that the dendrimer molecules have no structural defects. Although a π-conjugated system was used as the bridging ligand, electronic and fluorescence spectra suggested that the interaction among the platinum-acetylide moieties in the dendrimers was small.

Synthesis of hyperbranched platinum-poly(yne) polymers by self polycondensation

A hyperbranched polymer constructed by platinum-acetylide units has been synthezied by self polycondensation of a dinuclear platinum complex having one terminal acetylene and two platinum-chloride groups as an AB2 monomer in the presence of a c

Convergent route to organometallic dendrimers composed of platinum- acetylide units

The third-generation dendrimer with 45 platinum atoms (shown schematically) was synthesized efficiently by a convergent methodology in which two different trialkylsilyl groups (symbolized by the nodal points) are used to protect the bridging triethynylben