162715-91-5

Upstream product

• 22588-73-4 1,4-dihexylbenzene 
• 111-25-1 1-bromo-hexane 
• 624-38-4 para-diiodobenzene 
• 3761-92-0 n-hexylmagnesium bromide 
• 168213-37-4 1,4-di(hex-1-yn-1-yl)benzene 
• 693-02-7 hex-1-yne 
• 106-46-7 para-dichlorobenzene 

Downstream Products

• 188781-60-4 2,5-dihexyl-1,4-diprop-1-ynylbenzene 
• 220280-67-1 1,4-dihexyl-2-(3-hydroxyprop-1-ynyl)-5-iodobenzene 
• 850497-51-7 1,4-dihexyl-2-iodo-5-(phenylethynyl)benzene 
• 712267-53-3 2,5-dihexyl-1,4-dibut-1-ynylbenzene 
• 949079-62-3 C₃₃H₄₆NOI 
• 949079-66-7 C₄₈H₆₄N₂O₂ 
• 949079-63-4 C₅₃H₇₄NOI 
• 949079-68-9 C₈₈H₁₂₀N₂O₂ 
• 949079-71-4 C₂₀H₃₂ION 
• 947395-34-8 C₁₈H₃₀BO₂I 
• 167319-44-0 ((2,5-dihexyl-1,4-phenylene)bis(ethyne-2,1-diyl))bis(trimethylsilane) 
• 1191252-24-0 C₅₉H₇₇ISi 
• 1191252-26-2 C₈₂H₉₈Si₂ 
• 1253907-29-7 C₄₂H₆₁IO 

Relevant academic research and scientific papers

Ferrocene metallopolymers of intrinsic microporosity (MPIMs)

We show here that non-network metallopolymers can possess intrinsic microporosity stemming from contortion introduced by metallocene building blocks. Metallopolymers constructed from ferrocenyl building blocks linked by phenyldiacetylene bridges are synth

Intermolecular On-Surface σ-Bond Metathesis

Silylation and desilylation are important functional group manipulations in solution-phase organic chemistry that are heavily used to protect/deprotect different functionalities. Herein, we disclose the first examples of the σ-bond metathesis of silylated alkynes with aromatic carboxylic acids on the Ag(111) and Au(111) surfaces to give the corresponding terminal alkynes and silyl esters, which is supported by density functional theory calculations and further confirmed by X-ray photoelectron spectroscopy analysis. Such a protecting group strategy applied to on-surface chemistry allows self-assembly structures to be generated from molecules that are inherently unstable in solution and in the solid state. This is shown by the successful formation of self-assembled hexaethynylbenzene at Ag(111). Furthermore, it is also shown that on the Au(111) surface this σ-bond metathesis can be combined with Glaser coupling to fabricate covalent polymers via a cascade process.

On-surface reductive coupling of aldehydes on Au(111)

On-surface synthesis of a polyphenylene vinylene oligomer via reductive coupling of a terephthalaldehyde derivative on Au(111) is reported. Scanning tunneling microscopy and photoelectron spectroscopy experiments confirmed oxygen dissociation and its deso

Glaser coupling at metal surfaces

On-surface synthesis is a promising approach for constructing covalently bound nanostructures. However, the number of reliable chemical reactions suitable for on-surface chemistry is very limited. Arylalkynes can be coupled at various surfaces in a novel

Synthesis and solid-state investigations of oligo-phenylene-ethynylene structures with halide end-groups

In the field of material science functionalization of substrate surfaces (e.g. metal, graphite) with organic molecules is of increasing interest. Desirable targets are molecules with functional groups providing for two-dimensional assembly and three-dimen

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.

Macrocyclic cyclophanes with two and three α,ω-dichalcogena-1, 4-diethynylaryl units: Syntheses and structural properties

(Chemical Equation Presented) By means of four- and six-component cyclization reaction various cyclophanes were synthesized. The components were the di(lithium) salts of 1,4-di(ethynyl)benzene (11), 4,4′-di(ethynyl) biphenyl (13), 1,4-di(ethynyl)-2,5-di(n-hexyl)benzene (18), and 1,4-di(ethynyl)-2,5-di(n-propyl)benzene (19). These building blocks were reacted with α,ω-dithiocyanato-n-alkanes and α,ω- diselenocyanato-n-alkanes with n = 3-6. In the case of 10 also 1,1′-di(2-thiocyanatoethyl)cyclohexane (24) was reacted to afford a cyclophane comprising three subunits of 11. From most of the resulting macrocyclic cyclophanes (4(n) (n = 3, 5), 5, 6, 7(n), 8(n) (n = 3-6), 9(n) (n = 3, 5), and 10), we were able to grow single crystals. The X-ray analysis of 4(3), 7(3), 8(3), 8(4), 6, 7(5), and 8(5) revealed close contacts between the chalcogen atoms. These chalcogen-chalcogen interactions impose a ribbon-shape arrangement of molecules in 4(3) and a mutual crossing of two perdendicular planes built of 8(4) molecules. For 4(3) we found a close contact (3.28 A) between the π planes of two neighboring C6H4 rings of different molecules, whereas in 8(4) such a close contact (3.74 A) was due to an intermolecular interaction. Tubular stacking of the macrocyclic rings was found for 7(5) and 8(5) caused by a ladder-type intermolecular chalcogen-chalcogen interaction.

Synthesis of poly(2,5-thienyleneethynylene)s by alkyne metathesis

The formation of high molecular weight products by the synthesis of poly(2,5-trienylene ethylene) from alkyne metathesis was discussed. Coupling reactions of diethynylated aromatics with dihalogenated arenes was performed in the synthesis process using Sh

Selective cross-coupling of 1-ethynyl-4-iodobenzenes with activated arylacetylenes

Conditions were found for selective cross-coupling of 1-ethynyl-2,5- dihexyl-4-iodobenzene with arylethynyl-activated arylacetylenes. The reaction is not accompanied by homo- condensation of 1-ethynyl-2,5-dihexyl-4-iodobenzene.

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.