75867-44-6

Usage

Uses

Used in Organic Synthesis:
2,6-BIS(TRIMETHYLSILYLETHYNYL)PYRIDINE is used as a reagent for its powerful base and nucleophilic properties, facilitating a broad spectrum of chemical reactions in organic synthesis.
Used in Materials Science:
In the field of materials science, 2,6-BIS(TRIMETHYLSILYLETHYNYL)PYRIDINE is utilized for its potential in creating advanced materials, capitalizing on its unique electronic and optical attributes.
Used in Catalysis:
2,6-BIS(TRIMETHYLSILYLETHYNYL)PYRIDINE serves as a catalyst, contributing to the efficiency and selectivity of various chemical processes.
Used in Protection of Sensitive Functional Groups:
2,6-BIS(TRIMETHYLSILYLETHYNYL)PYRIDINE is used as a protecting agent for sensitive functional groups in organic chemistry, thanks to its trimethylsilyl groups.
Used in Development of Electronic Devices:
2,6-BIS(TRIMETHYLSILYLETHYNYL)PYRIDINE is explored for its applications in the development of electronic devices, leveraging its electronic and optical properties for innovative technological advancements.

Upstream product

• 626-05-1 2,6-Dibromopyridine 
• 1066-54-2 trimethylsilylacetylene 
• 250643-77-7 tris(2-(trimethylsilyl)ethynyl)indium 
• 2402-78-0 2,6-dichloropyridine 
• 1945-84-2 2-ethynylpyridine 

Downstream Products

• 75867-46-8 2,6-diethynylpyridine 
• 83965-72-4 2,6-bis(2-phenylethynyl)pyridine 
• 760952-79-2 2,6-bis(1-benzyl-1H-1,2,3-triazol-4-yl)pyridine 

Relevant academic research and scientific papers

Fine-Tuned Visible and Near-Infrared Luminescence on Self-Assembled Lanthanide-Organic Tetrahedral Cages with Triazole-Based Chelates

The construction of well-defined lanthanide complexes emitting in both the visible and near-infrared regions is of great importance due to their widespread applications in phosphors, light-emitting diodes, biosensors/probes, optical communications, etc. I

Synthesis, structural, photophysical and electrochemical studies of various d-metal complexes of btp [2,6-bis(1,2,3-triazol-4-yl)pyridine] ligands that give rise to the formation of metallo-supramolecular gels

2,6-Bis(1,2,3-triazol-4-yl)pyridine (btp) is a terdentate binding motif that is synthesised modularly via the CuAAC reaction. Herein, we present the synthesis of ligands 1 and 2 and the investigation of the coordination chemistry, photophysical behaviour

Rapid and efficient desilylation and deuteration of alkynylpyridines

We describe a rapid and efficient technique for the direct installation of deuterium atoms following the removal of trimethylsilyl groups from alkynylpyridines. Utilizing tetrabutylammonium fluoride in the presence of deuterium oxide, we observe up to 97% deuterium incorporation in as little as one minute of reaction time.

Click-chemistry-based bis-triazolylpyridine diphosphonate ligand for the sensitized luminescence of lanthanides in the solid state within the layers of γ-zirconium phosphate

The synthesis by means of 'click' chemistry of a new ligand bearing the bis-triazolylpyridine motif and pendant phosphonate groups is described. The topotactic phosphate/phosphonate exchange of the ligand into gamma-zirconium phosphate led to an organic-inorganic-layered material which revealed an excellent matrix to achieve the efficient sensitization of emitting lanthanides.

A pyrene-pyridyl nanooligomer as a methoxy-triggered reactive probe for highly specific fluorescence assaying of hypochlorite

A novel pyrene-pyridyl conjugated oligomer (OPP-OMe) was conveniently prepared by one-pot Sonogashira coupling. Intriguingly, it was found that introducing only one methoxy moiety at the 4-pyridyl position can be sufficient for creating an oligomer-based ultrafine reactive fluorescent nanoprobe, i.e., OPP-OMe NPs (ca. 2.5 nm in diameter). Spectral analyses and elucidation of the intermediate structure revealed that the methoxy triggered-oxidation, together with nanoaggregation of OPP-OMe NPs, results in rapid, specific and supersensitive sensing of hypochlorite (LOD, 0.3 nM, S/N = 3).

Macrocyclic: Vs. [2]catenane btp structures: Influence of (aryl) substitution on the self templation of btp ligands in macrocyclic synthesis

The synthesis of four 2,6-bis(1,2,3-triazol-4-yl)pyridine (btp) olefin based ligands 3, 4, 11 and 12 is described and their attempted use to form mechanically interlocked molecules using ring closing metatheses (RCM) reactions. The btp ligands were modified in two ways, in 3 and 4 the aryl substitution pattern was changed from 4th position to 3rd position and in the case of 11 and 12, the arms were replaced with aliphatic chains. Our study demonstrates that for all four ligands, the RCM reactions only result in the formation of macrocyclic structures, which in three of the cases, were structurally characterised in both solution (using NMR and HRMS) and in the solid-state using X-ray crystallography. NMR studies were also carried out to investigate if these ligands could preorganise in solution via hydrogen bonding interactions. This study provides a handle of how such precursor substitution can be used to direct the formation of macrocycles or mechanically interlocked structures.

Conformational control through co-operative nonconventional C - H-N hydrogen bonds

We report the design, synthesis, and crystal structure of a conjugated aryleneethynyl molecule, 2-(2-{4,5-dimethoxy-2-[2-(2,3,4-trifluorophenyl)ethynyl]phenyl}ethynyl)-6-[2-(pyridin-2-yl)ethynyl]pyridine, C30H17F3N2O2, that adopts a planar rhombus conformation in the solid state. The molecule crystallizes in the space group P , with Z = 2, and features two intramolecular sp2 -C - H-N hydrogen bonds that co-operatively hold the arylethynyl molecule in a rhombus conformation. The H atoms are activated towards hydrogen bonding since they are situated on a trifluorophenyl ring and the H-N distances are 2.470(16) and 2.646(16)?, with C - H-N angles of 161.7(2) and 164.7(2)°, respectively. Molecular electrostatic potential calculations support the formation of C - H-N hydrogen bonds to the trifluorophenyl moiety. Hirshfeld surface analysis identifies a self-complementary C - H-O dimeric interaction between adjacent 1,2-dimethoxybenzene segments that is shown to be common in structures containing that moiety.

Synthesis of pyridine-bridged bisferrocene and its pH value adjustable photoelectric properties

Four bisferrocenyl pyridine derivatives 2, 6-bis (ferrocenylethynyl) pyridine (3), 2, 6-bis (ferrocenylbutadiynyl) pyridine (8), 2, 6-bis (ferrocenylhexyltriynyl) pyridine (9), 2, 5-bis (ferrocenylbutadiynyl) pyridine (14) have been synthesized and photoe

Observation of an inversion in photophysical tuning in a systematic study of luminescent triazole-based osmium(II) complexes

In a systematic survey of luminescent bis(terdentate) osmium(II) complexes, a tipping point involving a reversal in photophysical tuning is observed whereby increasing stabilization of the ligand-based lowest unoccupied molecular orbital (LUMO) results in a blue shift in the optical absorption and emission bands. The complexes [Os(N^N′^N″)2]2+ [N^N′^N″ = 2,6-bis(1-phenyl-1,2,3-triazol-4-yl)pyridine (Os1), 2,6-bis(1-benzyl-1,2,3-triazol-4-yl)pyrazine (Os2), 6-(1-benzyl-1,2,3-triazol-4-yl)-2,2′-bipyridyl (Os3), 2-(pyrid-2-yl)-6-(1-benzyl-1,2,3-triazol-4-yl)pyrazine (Os4), 2-(pyrazin-2-yl)-6-(1-benzyl-1,2,3-triazol-4-yl)pyridine (Os5), and 6-(1-benzyl-1,2,3-triazol-4-yl)-2,2′-bipyrazinyl (Os6)] have been prepared and characterized, and all complexes display phosphorescence ranging from the orange to near-IR regions of the spectrum. Replacement of the central pyridine in the ligands of Os1 by the more π-accepting pyrazine in Os2 results in a 55 nm red shift in the triplet metal-to-ligand charge-transfer-based emission band, while a larger red shift of 107 nm is observed for the replacement of one of the triazole donors in the ligands of Os1 by a second pyridine ring in Os3 (λemmax = 702 nm). Interestingly, replacement of the central pyridine ring in the ligands of Os3 by pyrazine (Os4, λemmax = 702 nm) fails to result in a further red shift in the emission band. Reversal of the relative positions of the pyridine and pyrazine donors in Os5 (λemmax = 733 nm) compared to Os4 does indeed result in the expected red shift in the emission with respect to that for Os3 based on the increased π-acceptor character of the ligands present. However, an inversion in emission tuning is observed for Os6, in which the incorporation of a second pyrazine donor in the ligand architecture results in a blue shift in the optical absorption and emission maxima (λemmax = 710 nm). Electrochemical studies reveal that while incorporating pyrazine in the ligands indeed results in an expected anodic shift in the first reduction potential through stabilization of the ligand-based LUMO, there is also a concomitant anodic shift in the OsII/OsIII-based oxidation potential. This stabilization of the metal-based highest occupied molecular orbital (HOMO) thus nullifies the effect of stabilization of the LUMO in Os4 compared to Os3, resulting in these complexes having coincident emission maxima. For Os6, stabilization of the HOMO through the incorporation of two pyrazine donors in the ligand structure now exceeds stabilization of the LUMO, resulting in a larger HOMO?LUMO gap and a counterintuitive blue shift in the optical properties in comparison with those of Os5. While it is known that the replacement of ligands (e.g., replacing bipyridyl with bipyrazinyl) can result in a larger HOMO?LUMO energy gap through greater stabilization of the HOMO, these results importantly allow us to capture the tipping point at which this inversion in photophysical tuning occurs. This therefore enables us to explore the limits available in emission tuning with a relatively simple and minimalist ligand structure.

Structure-Affinity Relationships (SARs) and Structure-Kinetics Relationships (SKRs) of Kv11.1 Blockers

Kv11.1 (hERG) blockers with comparable potencies but different binding kinetics might display divergent pro-arrhythmic risks. In the present study, we explored structure-kinetics relationships in four series of Kv11.1 blockers next to their structure-affinity relationships. We learned that despite dramatic differences in affinities and association rates, there were hardly any variations in the dissociation rate constants of these molecules with residence times (RTs) of a few minutes only. Hence, we synthesized 16 novel molecules, in particular in the pyridinium class of compounds, to further address this peculiar phenomenon. We found molecules with very short RTs (e.g., 0.34 min for 37) and much longer RTs (e.g., 105 min for 38). This enabled us to construct a kon-koff-KD kinetic map for all compounds and subsequently divide the map into four provisional quadrants, providing a possible framework for a further and more precise categorization of Kv11.1 blockers. Additionally, two representative compounds (21 and 38) were tested in patch clamp assays, and their RTs were linked to their functional IC50 values. Our findings strongly suggest the importance of the simultaneous study of ligand affinities and kinetic parameters, which may help to explain and predict Kv11.1-mediated cardiotoxicity.