220280-76-2

Upstream product

• 22588-73-4 1,4-dihexylbenzene 
• 1253907-24-2 C₃₃H₅₄OSi 
• 220280-67-1 1,4-dihexyl-2-(3-hydroxyprop-1-ynyl)-5-iodobenzene 
• 162715-91-5 1,4-dihexyl-2,5-diiodobenzene 
• 220280-70-6 3-{2,5-Dihexyl-4-[(triisopropylsilanyl)-ethynyl]-phenyl}-prop-2-yn-1-ol 

Downstream Products

• 220280-80-8 3-(4-{2,5-Dihexyl-4-[(triisopropylsilanyl)-ethynyl]-phenylethynyl}-2,5-dihexyl-phenyl)-prop-2-yn-1-ol 
• 312624-88-7 {2,5-dihexyl-4-[4-(tetrahydro-pyran-2-yloxy)-phenylethynyl]-phenylethynyl}-triisopropyl-silane 
• 437985-40-5 4-{2,5-dihexyl-4-[(triisopropylsilanyl)-ethynyl]-phenylethynyl}-benzoic acid methyl ester 
• 437985-46-1 4-(4-ethynyl-2,5-dihexyl-phenylethynyl)-benzoic acid methyl ester 
• 437985-54-1 C₃₈H₄₂O₄ 
• 312624-90-1 2-[4-(4-ethynyl-2,5-dihexyl-phenylethynyl)-phenoxy]-tetrahydro-pyran 
• 312624-95-6 C₅₆H₆₆O₂ 
• 312624-93-4 C₆₆H₈₂O₄ 
• 220280-82-0 [4-(4-Ethynyl-2,5-dihexyl-phenylethynyl)-2,5-dihexyl-phenylethynyl]-triisopropyl-silane 
• 1236050-69-3 C₅₁H₆₈N₂O₂Si 
• 1236050-57-9 C₂₆H₂₆O₄ 
• 1236050-89-7 C₄₄H₆₂O₂Si 
• 1027306-61-1 C₄₆H₆₂O₂ 
• 1236050-94-4 C₅₄H₈₀OSi 

Relevant academic research and scientific papers

Polar tagging in the synthesis of monodisperse oligo(p-phenyleneethynylene) s and an update on the synthesis of oligoPPEs

One important access to monodisperse (functionalized) oligoPPEs is based on the orthogonality of the alkyne protecting groups triisopropylsilyl and hydroxymethyl (HOM) and on the polar tagging with the hydroxymethyl moiety for an easy chromatographic separation of the products. This paper provides an update of this synthetic route. For the deprotection of HOM protected alkynes, γ-MnO2 proved to be better than (highly) activated MnO 2. The use of HOM as an alkyne protecting group is accompanied by carbometalation as a side reaction in the alkynyl-aryl coupling. The extent of carbometalation can be distinctly reduced through substitution of HOM for 1-hydroxyethyl. The strategy of polar tagging is extended by embedding ether linkages within the solubilising side chains. With building blocks such as 1,4-diiodo-2,5-bis(6-methoxyhexyl) less steps are needed to assemble oligoPPEs with functional end groups and the isolation of pure compounds becomes simple. For the preparation of 1,4-dialkyl-2,5-diiodobenzene a better procedure is presented together with the finding that 1,4-dialkyl-2,3-diiodobenzene, a constitutional isomer of 1,4- dialkyl-2,5-diiodobenzene, is one of the byproducts.

EPR probes with well-defined, long distances between two or three unpaired electrons

The synthesis of rod- and star-shaped compounds carrying two or three spin labels as end groups is described. The unpaired electrons are 2.8-5.1 nm apart from each other. The shape-persistent scaffolds were obtained through Pd-Cu-catalyzed alkynyl-aryl coupling and Pd-Cu-catalyzed, alkyne dimerization in the presence of oxygen using p-phenyleneethynylene as the basic shape-persistent building block. The spin label 1-oxyl-2,2,5,5-tetramethylpyrroline-3-carboxylic acid (4) was attached through esterification of the terminal phenolic OH groups of the scaffold.

Synthesis of monodisperse oligo(para-phenyleneethynylene)s using orthogonal protecting groups with different polarity for terminal acetylene units

Monodisperse oligo(para-phenyleneethynylene)s (oligo-PPEs) were synthesized by a divergent-convergent synthesis starting from 1,4-dihexyl-2- (3-hydroxyprop-1-ynyl)-5-[2(triisopropylsilyl)ethynyl]benzene and using the Pd/Cu-catalyzed alkyne-aryl coupling.