CAS Number 1469704-61-7
Like the benchmark green TADF emitter and photocatalyst, 3CzClIPN belongs to the isophthalonitrile (IPN) family bearing three electron-donating carbazole at meta-positions, one chlorine and two nitrile electron-accepting units. 3CzClIPN is a popular photocatalyst that is widely used in a variety of organic reactions such as visible-light driven photocatalytic CO2 reduction and site-selective remote C(sp3)–H heteroarylation of amides. The chemical modification of 4CzIPN to 3CzClIPN by replacing one of the carbazolyl groups to chlorine increases the oxidative ground state potential, and the chlorine group increases the charge transfer character of the relevant states. Due to the lowered ∆EST, reverse intersystem crossing (RISC) is dramatically increased in 3CzClIPN by a factor of 3–5. However, the photoluminescence quantum yield (PLQY) is reduced due to nonradiative transitions from the excited singlet to the ground state.
Regioselective vinylation of aromatic and aliphatic aldehydes can be realized by the use of 3CzClIPN as the photocatalyst and Hantzsch's ester as the sacrificial organic reductant under visible light irradiation without using organometallic reagents or hydrides in stoichiometric amounts.
CAS number | 1469704-61-7 |
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Full name | 2,4,6-Tri(9H-carbazol-9-yl)-5-chloroisophthalonitrile |
Chemical formula | C44H24ClN5 |
Molecular weight | 658.15 g/mol |
Absorption* |
λmax ~ 325 nm in N,N-dimethylacetamide |
Fluorescence | λem 545 nm in acetonitrile |
HOMO/LUMO | E1/2 = - 1.61 V (vs. Fc+ /Fc) |
Classification / Family | Carbazole, Phthalonitrile, TADF materials, Photosensitizers, Photocatalysts |
Purity | >98.0% (1H NMR) |
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Melting point | >300 °C. |
Appearance | Yellow/brown powder/crystals |
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