3CzClIPN

CAS Number 1469704-61-7

Materials, Semiconducting Molecules, TADF Materials

3CzClIPN, Isophthalonitrile Photocatalyst

TADF Photosensitizer, CAS No. 1469704-61-7, 2,4,6-Tri(9H-carbazol-9-yl)-5-chloroisophthalonitrile

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 ∆E_ST, 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.

General Information

CAS number	1469704-61-7
Full name	2,4,6-Tri(9H-carbazol-9-yl)-5-chloroisophthalonitrile
Chemical formula	C₄₄H₂₄ClN₅
Molecular weight	658.15 g/mol
Absorption*	λ_max ~ 325 nm in N,N-dimethylacetamide
Fluorescence	λ_em 545 nm in acetonitrile
HOMO/LUMO	E_1/2= - 1.61 V (vs. Fc+ /Fc)
Classification / Family	Carbazole, Phthalonitrile, TADF materials, Photosensitizers, Photocatalysts

Product Details

Purity	>98.0% (1H NMR)
Melting point	>300 °C.
Appearance	Yellow/brown powder/crystals

Chemical Structure

MSDS Documentation

3czclipn - 1469704-61-7 - 2,4,6-tri(9H-carbazol-9-yl)-5-chloroisophthalonitrile MSDS 3CzClIPN MSDS sheet

Literature and Reviews

E. Speckmeier et al. (2018); A Toolbox Approach To Construct Broadly Applicable Metal-Free Catalysts for Photoredox Chemistry: Deliberate Tuning of Redox Potentials and Importance of Halogens in Donor–Acceptor Cyanoarenes, J. Am. Chem. Soc., 140 (45), 15353–15365; DOI: 10.1021/jacs.8b08933.
M. Streiter et al. (2020); Impact of Chlorine on the Internal Transition Rates and Excited States of the Thermally Delayed Activated Fluorescence Molecule 3CzClIPN, J. Phys. Chem. C, 124 (28), 15007–15014; DOI: 10.1021/acs.jpcc.0c03341.
H. Chen et al. (2019); Site-selective remote C(sp 3)–H heteroarylation of amides, Nat. Commun. 10, 4743 (2019); DOI: 10.1038/s41467-019-12722-4.

E. Bassan et al. (2023); Visible-light driven photocatalytic CO2 reduction promoted by organic photosensitizers and a Mn(I ) catalyst, Sustainable Energy Fuels, 7, 3454-3463; DOI: 10.1039/D3SE00546A.
F. Calogero et al. (2022); Dual Photoredox and Nickel Catalysed Reductive Coupling of Alkynes and Aldehydes, Adv. Synth. Catal., 364, 3410 – 3419; DOI: 10.1002/adsc.202200589.