3DPAFIPN

CAS Number 2260543-73-3

High Purity Sublimed Materials, Materials, Semiconducting Molecules, TADF Materials

Isophthalonitrile Photocatalyst

TADF cyanoarene photosensitizer available in sublimed (≥99%) and unsublimed (≥98%) grade

3DPAFIPN is a fluorinated isophthalonitrile (IPN) derivative with three diphenylamine (DPA) at meta-positions to each other. The absorption of 3DPAFIPN is red-shifted compared to its carbazole analogues such as 3CzClIPN due to the more electron-rich nature of DPA moieties compared to carbazole moieties. DPA substituted isophthalonitrile leads to the destabilization of the HOMO, resulting in smaller transition energies for visible-light absorption.

3DPAFIPN has been widely used as TADF photosensitizer as a donor–acceptor (D–A) type photocatalyst in a number of visible light-triggered synthetic procedures such as intramolecular cyclization, as well as the formation of C-C, C-N, and C-P chemical bonds. As a TADF photosensitizer, 3DPAFIPN is capable of inducing single electron transfer (SET) process upon irradiation with visible light, thereby offering a facile and efficient approach with a high degree of energy efficiency in catalysing chemical reactions under mild reaction conditions.

General Information

CAS number	2260543-73-3
Full name	2,4,6-Tris(diphenylamino)-5-fluoroisophthalonitrile
Chemical formula	C₄₄H₃₀FN₅
Molecular weight	647.74 g/mol
Photocatalyst Activation	390 nm
Fluorescence	λ_em 525 nm in acetonitrile
HOMO/LUMO	E_1/2= - 1.94 V (vs. Fc+ /Fc) [4]
Classification / Family	Triphenylamine, Phthalonitrile, Cyanoarene, TADF materials, Photosensitizers, Photocatalysts

Product Details

Purity	Unsublimed >98.0% (1H NMR), Sublimed > 99%
Melting point	n.a.
Appearance	Yellow powder/crystals

Chemical Structure

MSDS Documentation

3DPAFIPN 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.
F. Mohamadpour (2023); 3DPAFIPN as a halogenated dicyanobenzene‑based photosensitizer catalysed gram‑scale photosynthesis of pyrano[2,3‑d pyrimidine scaffolds, Sci. Rep., 13, 13142; DOI: 0.1038/s41598-023-40360-w.
F. Mohamadpour et al. (2023); Halogenated dicyanobenzene-based photosensitizer (3DPAFIPN) as a thermally activated delayed fluorescence (TADF) used in gram-scale photosynthesis 3,4-dihydropyrimidin-2-(1H)-one/thione derivatives via a consecutive visible-light-induced electron-transfer pathway, Front. Chem., 12, 1361266, DOI 10.3389/fchem.2024.1361266.

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.