246141-52-6

Upstream product

• 75867-39-9 4-trimethylsilylethynyl aniline 
• 935-14-8 1,4-diethynylbenzene 
• 540-37-4 p-aminoiodobenzene 
• 624-38-4 para-diiodobenzene 
• 14235-81-5 4-Ethynylaniline 

Downstream Products

• 552299-26-0 1,4-bis[(4'-azidophenyl)ethynyl]benzene 
• 1443445-87-1 Et₂H₂tpeba 

Relevant academic research and scientific papers

Synthesis of Structurally Diverse Emissive Molecular Rotors with Four-Component Ugi Stators

The use of the multicomponent Ugi reaction to rapidly prepare a library of dumbbell-like molecular rotors is highlighted here. The synthetic strategy consisted of the atom-economic access to 15 bulky and structurally diverse iodinated stators, which were cross-coupled to the 1,4-diethynylphenylene rotator. From those experiments, up to six rotors 1a-c and 1l-n were obtained, with yields ranging from 35 to 69% per coupled C-C bond. In addition to the framework diversity, five of these compounds showed aggregate-enhanced emission properties thanks to their conjugated 1,4-bis(phenylethynyl)benzene cores, a property that rises by increasing the water fraction (fw) in their THF solutions. The results highlight the significance of the diversity-oriented synthesis of rapid access to new molecular fluorescent rotors.

Palladium(II) complex for catalyzing sonogashira coupling reactions and a method thereof

A palladium(II) complex which catalyzes the Sonogashira coupling reaction efficiently under aerobic condition and a method of employing the palladium(II) complex to synthesize internal alkynes. The palladium(II) complex is an effective catalyst for the co

Synthesis of functionalized alkynes via palladium-catalyzed Sonogashira reactions

A highly efficient protocol for the copper and phosphine free Sonogashira cross-coupling reactions of aryl iodides with terminal alkynes under aerobic conditions has been developed. Using 1 mol % of the palladium-bis(oxazoline) complex, Pd-BOX A, in the p

Simplifying the conductance profiles of molecular junctions: The use of the trimethylsilylethynyl moiety as a molecule-gold contact

Conductance across a metal|molecule|metal junction is strongly influenced by the molecule-substrate contacts, and for a given molecular structure, multiple conductance values are frequently observed and ascribed to distinct binding modes of the contact at each of the molecular termini. Conjugated molecules containing a trimethylsilylethynyl terminus, -C≡CSiMe 3 give exclusively a single conductance value in I(s) measurements on gold substrates, the value of which is similar to that observed for the same molecular backbone with thiol and amine based contacting groups when bound to under-coordinated surface sites.

Dicopper(II) metallacyclophanes with oligo(p-phenylene-ethynylene) spacers: Experimental foundations and theoretical predictions on potential molecular magnetic wires

Two novel double-stranded dicopper(II) metallacyclophanes of formula (nBu4N)4[Cu2(dpeba)2] ·4MeOH·2Et2O (1) and (nBu4N) 4[Cu2(tpeba)2]·12H2O (2)

Secondary face-to-face 2-2' β-cyclodextrin dimers linked with fluorescent rigid spacer arms: A cyclodextrin-based ratiometric sensor for bile salts

The synthesis of a series of β-cyclodextrin (CD) dimers in which the two macrocycle units are linked by rigid-rod phenylene-ethynylene tethers of different length and shape through the cyclodextrin secondary sides is reported. The synthesis involves Sonog

A study on the electro-oxidation and electropolymerization of a new OPE linear molecule by EQCM and in situ FTIR spectroelectrochemistry

A novel symmetric conjugated oligo(phenylene-ethynylene) (OPE) linear molecule (1,4-bis(4-aminophenylethynyl)benzene); BAB) was synthesized by Sonogashira cross-coupling reactions. The structure and purity of the compound were confirmed by 1H N

Limits of delocalization in through-conjugated dinitrenes: Aromatization or bond formation?

(Matrix presented) Dinitrenes 4 and 5 both can form quinonoidal structures by conjugative bond formation. However, ESR spectroscopy detects a thermally populated, excited-state, triplet quinonoidal structure only for 4, with a zero-field splitting of |D/hc| = 0.0822 cm-1, |E/hc| ? 0.0 cm-1. The tendency to maintain aromaticity in the additional ring of 5 favors a dinitrene structure (with one less formal π-bond) over a quinonoidal structure. The thermally populated quintet state of 5 has a zero-field splitting of |D/hc| = 0.287 cm-1, |E/hc| ≤ 0.002 c m-1.

Linking metal centres with diimido ligands: Synthesis, electronic and molecular structure and electrochemistry of organometallic ditungsten complexes [{WCl2(Ph2PMe)2(CO)}2(N-X-N)] (X = π-conjugated organic)

Tungsten(IV) diimido-bridged complexes [{WCl2(Ph2PMe)2(CO)}(μ-N-X-N)] have been prepared via oxidative addition of diisocyanates to two equivalents of [WCl2(Ph2PMe)4]. para-Substituted monoimido complexes [WCl2(Ph2PMe)2(CO)(NC6H 4X-p)] (X = I, Br or C≡CPh) have also been prepared but attempts to couple the X = I complex as a route to diimido-bridged complexes were unsuccessful. All complexes are air-stable crystalline solids and five diimido (N-X-N = p-NC6H4N, p-N-o-MeC6H3N, p-N(o-MeOC6H3C6H3OMe-o)N, 1,5-NC10H6N or m-NC6H4N) and one monoimido complex (X = I) have been characterised crystallographically. All show the same gross structural features, namely a trans arrangement of phosphines and cis chlorides. The central aryl ring generally lies approximately in the Cl2(CO) plane (torsional angles 4.1-26.1°) except for one complex in which the ring lies almost perpendicular to this (torsional angle 80.2°). A series of density functional calculations conducted on model mono- and di-imido tungsten-(VI) and -(V) compounds indicated that the most stable aryl ring orientation is perpendicular to the plane containing the trans phosphines, i.e. as found in all cases except one (N-X-N = p-NC6H4N). The anomaly in the latter may be due to cocrystallisation with chlorobenzene. In order to assess the degree of communication between the tungsten(IV) centres through the highly π-conjugated diimido linkages, electrochemical studies have been carried out. All diimido-bridged complexes show two closely spaced oxidative processes at low temperature indicative of weak electronic communication. The reductive chemistry of the para-phenylene bridged complexes is different from other diimido complexes, displaying two closely spaced reductive processes. Spectro-electrochemical studies have also been carried out on N-X-N = p-NC6H4N, oxidation at +1.2 V leading to CO loss. In order to gain further insight into the nature of the electronic communication between metal centres density functional calculations were carried out and were generally in agreement with the electrochemical results, suggesting that there is at best a weak interaction between the metal centres in these π-conjugated diimido-bridged complexes.