335378-29-5

Upstream product

• 188003-93-2 triisopropyl((2-((trimethylsilyl)ethynyl) phenyl)ethynyl)silane 
• 583-55-1 1-Bromo-2-iodobenzene 
• 38274-16-7 2-bromo-1-(trimethylsilylethynyl)benzene 
• 89343-06-6 tris-iso-propylsilyl acetylene 
• 1067905-73-0 (2-(2-(2,2-dibromovinyl)phenyl)ethynyl)triisopropylsilane 

Downstream Products

• 214628-10-1 2-(triisopropylsilylethynyl)-1-(6-trimethylsilyl-1,3,5-hexatriynyl)benzene 
• 214628-16-7 1-(triisopropylsilyl)ethynyl-2-[(E)-6-(trimethylsilyl)hex-3-ene-1,5-diynyl]benzene 
• 351389-19-0 C₂₉H₃₉N₃Si 
• 335378-20-6 cis-1,6-bis(2'-(triisopropylsilylethynyl)phenyl)hex-3-en-1,5-diyne 
• 381173-13-3 1-[(Triisopropylsilanyl)-ethynyl]-2-((Z)-6-trimethylsilanyl-hex-3-ene-1,5-diynyl)-benzene 
• 1026510-52-0 8,9-bis-(2-ethynyl-phenylethynyl)-2,3-dihydro-1H-3a,7a-etheno-indene 
• 439588-87-1 C₂₀H₁₀S 
• 760975-27-7 1-butylsulfanylethynyl-2-ethynyl-benzene 
• 482294-20-2 1-((3Z,7Z)-Deca-3,7-diene-1,5,9-triynyl)-2-ethynyl-benzene 
• 482294-19-9 [((Z)-2-Hex-3-ene-1,5-diynyl)-phenylethynyl]-triisopropyl-silane 
• 381173-15-5 1-[(Triisopropylsilanyl)-ethynyl]-2-((3Z,7Z)-10-trimethylsilanyl-deca-3,7-diene-1,5,9-triynyl)-benzene 
• 214628-17-8 C₅₀H₅₆Si₂ 
• 214628-18-9 C₅₂H₅₆Si₂ 
• 383404-38-4 C₅₂H₅₈Si₂ 

Relevant academic research and scientific papers

Dimeric Indenofluorene-Extended Tetrathiafulvalene Motif for Enhanced Intramolecular Complexation

Tetrathiafulvalene (TTF) is a redox-active compound, which reversibly undergoes two one-electron oxidations to give stable species. Several features of TTF, such as redox and optical properties as well as geometry and self-associating nature, can be tuned by extension of the conjugated system with an aromatic linker such as an indenofluorene (IF) moiety. In this work we present the synthesis of a novel dimeric scaffold of IF-extended TTF (IF-TTF) in which the units are linked by a rigid 1,4-bis(2-ethynylphenyl)buta-1,3-diyne moiety. 1H-NMR spectroscopic studies reveal that the scaffold is highly prone to form intramolecular IF-TTF dimer complexes even in the neutral form, and stable radical cation species were formed in solution upon chemical oxidation with tris(4-bromophenyl)ammoniumyl hexachloroantimonate (‘magic blue’). Electrocrystallization of the rigid scaffold yielded a semi-conducting material, which proved to be stable at ambient temperature and air.

Radiaannulenes: Synthesis, electrochemistry, and solid-state structure

Two new carbon-rich macrocycles (radiaannulenes) have been synthesized, and they possess an unsaturated carbon framework that is intermediate between that of linearly-conjugated dehydrobenzannulenes and cross-conjugated expanded radialenes. The Royal Soci

Photochemical C2-C6 cyclization of enyne-allenes: Detection of a fulvene triplet diradical in the laser flash photolysis

(Chemical Equation Presented) A series of enyne-allenes, with and without benzannulation at the ene moiety and equipped with aromatic and carbonyl groups as internal triplet sensitizer units at the allene terminus, was synthesized. Both sets, the cyclohexenyne-allenes and benzenyne-allenes, underwent thermal C2-C6 cyclization exclusively to formal ene products. In contrast, the photochemical C2-C6 cyclization of enyne-allenes provided formal Diels-Alder and/or ene products, with higher yields for the benzannulated systems. A raise of the temperature in the photochemical cyclization of enyne-allene 1b′ led to increasing amounts of the ene product in relation to that of the formal Diels-Alder product. Laser flash photolysis at 266 and 355 nm as well as triplet quenching studies for 1b,b′ indicated that the C2-C6 cyclization proceeds via the triplet manifold. On the basis of a density functional theory (DFT) study, a short-lived transient (r = 30 ns) was assigned as a triplet allene, while a long-lived transient (τ = 33 μs) insensitive to oxygen was assigned as fulvene triplet diradical. An elucidation of the reaction mechanism using extensive DFT computations allowed rationalization of the experimental product ratio and its temperature dependence.

Structure-property investigations of conjugated thiophenes fused onto a dehydro[14]annulene scaffold

(Chemical Equation Presented) A series of 12 thieno-fused macrocycles based on the dehydro[14]annulene framework have been prepared. Studies have focused on the optical and electronic properties of the dehydrobenzothieno[14]annulenes (DBTAs) and dehydrothieno[14]annulenes (DTAs) utilizing NMR spectroscopy, UV-vis spectrophotometry, electrochemistry, and DFT computations. X-ray crystal structures were also obtained for two of the macrocycles. The structure-property relationships were found to vary significantly based on the relative orientation of the thiophenes. The stability, properties, and reactivity of these macrocycles were found to be more typical of dehydroannulenes rather than oligothiophenes.

A versatile synthetic route to dehydrobenzoannulenes via in situ generation of reactive alkynes

This paper outlines the development of a protocol that allows in situ generation of unstable alkynes under Pd-catalyzed cross-coupling conditions. Cu-mediated intramolecular cyclization of the resultant α,ω-polyynes provides dehydrobenzoannulenes as singular species, in very good overall yields, and in a variety of topologies that are inaccessible by traditional routes or previously available in low yield only. In addition, we will discuss the solid-state structure and reactivity of these macrocycles, as well as the ability of the planar dehydrobenzoannulenes to support weak induced ring currents.

Synthesis and spectroscopic studies of expanded planar dehydrotribenzo[n]annulenes containing one or two isolated alkene units

Dehydrobenzoannulene derivatives 5-7 containing isolated alkene linkages were synthesized by combining an in-situ Pd/Cu-mediated cross-coupling with an intramolecular cyclization strategy. 1H NMR studies of these macrocycles and comparison with

Diatropicity of dehydrobenzo[14]annulenes: Comparative analysis of the bond-fixing ability of benzene on the parent 3,4,7,8,9,10,13,14-octadehydro[14]annulene

(matrix presented) We report the synthesis of 3,4,7,8,9,10,13,14-octadehydro[14]annulene (1) and detail a comparative aromaticity study with its benzannelated derivatives (e.g., 2 and 3).

Bis(enediyne) macrocycles: Synthesis, reactivity, and structural analysis

We describe below the syntheses of five macrocycles possessing two enediyne warheads, along with the structural and thermal analyses of these bis(enediyne) compounds. The solid-state packing of compound 6 suggests the possibility for the molecule to undergo a topochemical diacetylene polymerization. (C) 2000 Elsevier Science Ltd.

Synthesis of expanded planar dehydrobenzoannulenes: Weakly diatropic, weakly paratropic, or atropic?

Use of a Cu/Pd cross-coupling strategy has led to the synthesis of the first dehydrobenzoannulenes containing triacetylenic linkages. NMR studies of these macrocycles and comparison with other known systems indicate that, in spite of their large size and extensive benzannelation, dehydrobenzoannulenes possess weak induced ring currents.