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Upstream product

• 589-87-7 1,4-bromoiodobenzene 
• 63697-96-1 4-Ethynylbenzaldehyde 
• 1122-91-4 4-bromo-benzaldehyde 
• 77123-57-0 4-[(trimethylsilyl)ethynyl]bezaldehyde 
• 766-96-1 4-bromo-1-ethynylbenzene 
• 15164-44-0 p-(iodophenyl)carboxaldehyde 

Downstream Products

• 1058737-77-1 C₂₃H₁₇BrN₂ 
• 1108614-17-0 4-((4-((trimethylsilyl)ethynyl)phenyl)ethynyl)benzaldehyde 

Relevant academic research and scientific papers

Synthesis, antibacterial and anticancer activity, and docking study of aminoguanidines containing an alkynyl moiety

Two series of aminoguanidines containing an alkynyl moiety were designed, synthesised, and screened for antibacterial and anticancer activities. Generally, the series 3a–3j with a 1,2-diphenylethyne exhibited better antibacterial activity than the other series (6a–6k) holding 1,4-diphenylbuta-1,3-diyne moiety antibacterial activity. Most compounds in series 3a–3j showed potent growth inhibition against the tested bacterial strains, with minimum inhibitory concentration (MIC) values in the range 0.25–8 μg/mL. Compound 3g demonstrated rapid and persistent bactericidal activity at 2 × MIC. The resistance study revealed that resistance of the tested bacteria towards 3g is not easily developed. Molecular docking studies revealed that compounds 3g and 6e bind strongly to the LpxC and FabH enzymes. Moreover, excellent activity of selected compounds against the growth of cancer cell lines A549 and SGC7901 was also observed, with IC50 values in the range 0.30–4.57 μg/mL. These findings indicate that compounds containing the aminoguanidine moiety are promising candidates for the development of new antibacterial and anticancer agents.

Carbazole-Terpyridine Donor-Acceptor Dyads with Rigid π-Conjugated Bridges

A series of molecules in which 9H-carbazole (electron donor, D) and 2,2′:6′,2′′-terpyridine (electron acceptor, A) are connected through rigid π-conjugated bridges (D-π-A systems) have been synthesized and their photophysical properties examined in detail, with the support of DFT calculations. The bridges are made of different sequences of ethynylene, phenylene, and anthracene groups. The synthetic strategies involve condensation of 2-acetylpyridine with the aromatic aldehyde moiety on different functionalized π-conjugated bridges and couplings with carbazole derivatives. The system incorporating anthracene in the bridge shows the typical absorption and emission fingerprints of this polycyclic hydrocarbon. The other systems have HOMOs and LUMOs centred, respectively, over the carbazole and the bridge and exhibit solvatochromic charge-transfer (CT) luminescence with high photoluminescence yield up to 70 %, except when an ethynylene unit is directly attached to the carbazole ring, due to a trans-bent non-emissive π–σ* excited state.

Influence of a D-π-A system through a linked unit of double and triple bonds in a triarylene bridge for dye-sensitised solar cells

Herein, eight metal-free organic dyes (YH-1-YH-8) containing olefin or acetylene as π-spacer linkages in a triarylene bridge were synthesised. Moreover, two dyes (1N-PPP and 1N-PPS) without olefin and triple bonds as π-spacer linkages were used as references. The photophysical and electrochemical properties of the dyes were characterised, and the dyes were then used to fabricate dye-sensitised solar cells (DSSCs). We demonstrated the use of a D-π-A dipolar system by employing arylamine derivatives as an electron donor, triarylene with iterative olefin or acetylene as a π-bridge, and cyanoacrylic acid as an electron acceptor. YH-1 had olefin as a repeating unit in the triarylene bridge and exhibited broad absorption, favourable short-circuit photocurrent density (Jsc), and favourable open-circuit voltage (Voc) when used in a film morphology with DCA as a coabsorbent. The optimal device exhibited a Jsc of 16.23 mA cm-2, a Voc of 650 mV, and a fill factor of 0.67, corresponding to an overall conversion efficiency of 7.08%. The photophysical properties of the DSSCs were analysed using time-dependent density functional theory with the B3LYP functional.

Systematic investigation of silver-carbon bonding in coordination frameworks with aryl ligands that contain ethynyl and ethenyl substituents

Single-crystal X-ray diffraction of a series of ten crystalline silver(I)-trifluoroacetate complexes that contained designed ligands, each of which was composed of an aromatic system that was functionalized with terminal and internal ethynyl groups and a

Regiospecifically α-13C-labeled porphyrins for studies of ground-state hole transfer in multiporphyrin arrays

(Figure Presented) Insight into the electronic communication between the individual constituents of multicomponent molecular architectures is essential for the rational design of molecular electronic and/or photonic devices. To clock the ground-state hole/electron-transfer process in oxidized multiporphyrin architectures, a p-diphenylethyne-linked zinc porphyrin dyad was prepared wherein one porphyrin bears two 13C atoms and the other porphyrin is unlabeled. The 13C atoms are located at the 1- and 9-positions (α-carbons symmetrically disposed to the position of linker attachment), which are sites of electron/spin density in the a1u HOMO of the porphyrin. The 13C labels were introduced by reaction of KS 13CN with allyl bromide to give the allyl isothiocyanate, which upon Trofimov pyrrole synthesis followed by methylation gave 2-(methyl-thio)pyrrole- 2-13C. Reaction of the latter with paraformaldehyde followed by hydrodesulfurization gave dipyrromethane-1,9-13C, which upon condensation with a dipyrromethane-1,9-dicarbinol bearing three pentafluorophenyl groups gave the tris(pentafluorophenyl)porphyrin bearing 13C labels at the 1,9-positions and an unsubstituted meso (5-) position. Zinc insertion, bromination at the 5-position, and Suzuki coupling with an unlabeled porphyrin bearing a suitably functionalized diphenylethyne linker gave the regiospecifically labeled zinc porphyrin dyad. Examination of the monocation of the isotopically labeled dyad via electron paramagnetic resonance (EPR) spectroscopy (and comparison with the monocations of benchmark monomers, where hole transfer cannot occur) showed that the hole transfer between porphyrin constituents of the dyad is slow (6 s -1) on the EPR time scale at room temperature. The slow rate stems from the a1u HOMO of the electron-deficient porphyrins, which has a node at the site of linker connection. In contrast, analogous dyads of electron-rich porphyrins (wherein the HOMO is a2u and has a lobe at the site of linker connection) studied previously exhibit rates of hole transfer that are fast (>5 × 107 s-1) on the EPR time scale at room temperature.