4DPAIPN, or 2,4,5,6-Tetrakis(diphenylamino)isophthalonitrile (CAS 1846598-27-3), is an isophthalonitrile-based photocatalyst from the cyanoarene family of TADF materials. It is supplied as a yellow powder or crystals in unsublimed grade with purity above 98.0% by 1H NMR.
The molecule follows a donor–acceptor design: a fully substituted benzene ring carries four diphenylamine donor groups and two nitrile acceptor groups in meta positions. This arrangement gives it a wide redox window and good chemical stability. Structurally it is a close relative of 4CzIPN, differing only in using diphenylamine groups where 4CzIPN uses carbazole groups.
As a metal-free organic photocatalyst, 4DPAIPN is used across a wide range of light-driven chemical transformations. One reported example is the phosphonylation of 4-alkyl-1,4-dihydropyridines (DHPs) with 9-fluorenyl o-phenylene phosphite under blue LEDs, using 1 mol% 4DPAIPN and 200 mol% triethylamine; the method works for primary, secondary and tertiary DHPs with broad substrate scope and strong functional group tolerance.
- Metal-free organic photocatalysis in visible-light-driven synthetic reactions.
- Photoinduced phosphonylation of 4-alkyl-1,4-dihydropyridines to prepare alkylphosphonates under blue LED irradiation.
- Use as a photosensitizer in photoredox chemistry research.
- Research on TADF donor–acceptor fluorophores and cyanoarene materials.
| Brand | Ossila |
|---|---|
| CAS number | 1846598-27-3 |
| Molecular formula | C56H40N6 |
| Purity | Unsublimed >98.0% (1H NMR) |
| Category | — |
| Pack sizes | 250 mg, 500 mg, 1 g |
| Physical form | Yellow powder/crystals |
| Storage | — |
- Product code: M2508B1
- Full Name: 2,4,5,6-Tetrakis(diphenylamino)isophthalonitrile
- Molecular Weight: 796.96 g/mol
- Photocatalyst Activation: 390 nm
- Fluorescence: λem 470 nm, 536 nm in acetonitrile
- Redox Potentials: E1/2 (*P/P−) = 1.21 V, E1/2 (P/P−) = -1.52 V
- Classification/Family: Triphenylamine, Phthalonitrile, Cyanoarene, TADF materials, Photosensitizers, Photocatalysts
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