2,4,6-Triphenylpyridine
TIMTEC-BB SBB007852 · 2,4,6-Triphenyl-pyridin · 2,4,6-Triphenylpyridine · PYRIDINE,2,4,6-TRIPHENYL
Identifiers & Physical Properties
| CAS No. | 580-35-8 |
|---|---|
| Molecular formula | C23H17N |
| Average molar mass | 307.4 g/mol |
| Monoisotopic mass | 307.13609954 g/mol |
| SMILES | c1ccc(-c2cc(-c3ccccc3)nc(-c3ccccc3)c2)cc1 |
| InChIKey | FRZHWQQBYDFNTH-UHFFFAOYSA-N |
| PubChem CID | 136370 |
| ChEMBL | CHEMBL27882 |
| EC No. | 622-170-0 |
| DTXSID | DTXSID30206730 |
Chemical & Physical Properties
| XLogP | 5.8 |
|---|---|
| Topological polar surface area | 12.9 |
| Hydrogen bond donors | 0 |
| Hydrogen bond acceptors | 1 |
| Rotatable bonds | 3 |
| Heavy atoms | 24 |
| Formal charge | 0 |
| Complexity | 334 |
| Melting point | 139.0 to 143.0 °C |
| Boiling point | 220-230 °C(Press: 0.3 Torr) |
| Density | 1.103±0.06 g/cm3(Predicted) |
| Storage conditions | Sealed in dry,Room Temperature |
| Physical state | powder to crystal |
| pKa (acidity coefficient) | 3.95±0.10(Predicted) |
| Color | White to Almost white |
| λmax | 312nm(EtOH)(lit.) |
| InChI | InChI=1S/C23H17N/c1-4-10-18(11-5-1)21-16-22(19-12-6-2-7-13-19)24-23(17-21)20-14-8-3-9-15-20/h1-17H |
| InChIKey | FRZHWQQBYDFNTH-UHFFFAOYSA-N |
| SMILES | C1(C2=CC=CC=C2)=NC(C2=CC=CC=C2)=CC(C2=CC=CC=C2)=C1 |
| GHS pictogram | GHS05,GHS06 |
| Signal word | Danger |
| GHS hazard statements | H315-H335-H413-H318-H301 |
| GHS precautionary statements | P264-P270-P301+P310-P321-P330-P405-P501-P280-P305+P351+P338-P310-P264-P280-P302+P352-P321-P332+P313-P362 |
| Customs code | 2933.39.9200 |
Safety & Regulations
| GHS classification | DangerH301 (97.5%): Toxic if swallowed [Danger Acute toxicity, oral]P261, P264, P264+P265, P270, P271, P273, P280, P301+P316, P302+P352, P304+P340, P305+P354+P338, P317, P319, P321, P330, P332+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 40 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Hazard Classes and Categories | Acute Tox. 3 (97.5%) |
| Customs code | 2933.39.9200 |
| Signal word | Danger |
| GHS pictogram | GHS05,GHS06 |
| GHS hazard statements | H315-H335-H413-H318-H301 |
| GHS precautionary statements | P264-P270-P301+P310-P321-P330-P405-P501-P280-P305+P351+P338-P310-P264-P280-P302+P352-P321-P332+P313-P362 |
Applications & Uses
Description
2,4,6-Triphenylpyridine, as a well-known electron-deficient heterocyclic unit, has been widely used as the conjugated molecular bridge linker to the polymer main chain. Pyridine and aromatic heterocyclic derivatives have been widely used as electron transporting/hole blocking materials in LED devices and LED blends because these units have many excellent properties of being a better chromophore, with high electron affinity, high thermal and oxidative stability, and ability for good charge injection and transporting building blocks[1].In addition, introduction of the pyridinyl moiety into the polymer backbone not only increases the electron affinity of the polymer, which makesthepolymer moreresistantto oxidation and also gives the polymer better electron-transporting properties, but also avoids fluorescence quenching due to the intersystem crossing (ISC) effect of the heavy atom. Some of them have been introduced into the polymer backbones to realize the desirable opto electronic materials.
Uses
2,4,6-Triphenylpyridine is a pyridine compound that acts as a neutral leaving group in palladium(0)-catalysed nucleophilic allylation reactions. In addition, three novel conjugated polymers based on the 2,4,6-triphenylpyridine moiety can be synthesised via the palladium-catalysed Sonogashira coupling reaction. These three polymers, P-1, P-2 and P-3, all exhibit strong fluorescence emission, characterised by a large Stokes shift and high quantum yield.