Diphenyl-1-pyrenylphosphine  (Synonyms: DPPP)

Diphenyl-1-pyrenylphosphine (DPPP) is a functional organic molecule with both fluorescent properties and metal coordination ability, which is commonly used in materials and coordination chemistry research. Upon exposure to ultraviolet light, Diphenyl-1-pyrenylphosphine undergoes photoinduced phosphorus atom oxidation to form O-DPPP, triggering a transition from aggregation-induced emission (AIE) to aggregation-caused quenching (ACQ). Diphenyl-1-pyrenylphosphine reacts stoichiometrically with lipid hydroperoxides to produce fluorescent diphenyl-1-pyrenylphosphine oxide. Diphenyl-1-pyrenylphosphine can insert into cell membranes to monitor lipid peroxidation processes in living cells^[1][2][3].

Diphenyl-1-pyrenylphosphine (DPPP) exhibits aggregation-induced emission (AIE) behavior in the H₂O/EtOH mixed system, with an α_AIE value of 126.1, and displays unique water-phase ratio-dependent fluorescence characteristics in the monomer, dimer and aggregated states^[1].
Diphenyl-1-pyrenylphosphine (10 μmol/L; irradiated with 365 nm UV light at 12.8 mW/cm² for 3 min) undergoes a light-triggered oxidation reaction to form O-DPPP after irradiation with 365 nm UV light (treated at 12.8 mW/cm² for 3 min). It converts from an AIE molecule to an ACQ molecule, exhibiting significant fluorescence changes in pure EtOH and pure H₂O^[1].
Diphenyl-1-pyrenylphosphine (1 mM; 5 min) reacts with MeLOOH and hydrogen peroxide in a chloroform/methanol (1/1) solution at 37°C, and forms the fluorescent product DPPPNO^[2] after 5 min of incubation, respectively.
Diphenyl-1-pyrenylphosphine (167-880 μM) integrates into human histiocytic lymphoma U937 cells, localizing to the cytoplasmic membrane instead of the nucleus^[3].
Diphenyl-1-pyrenylphosphine (167 μM; 5 min) preferentially reacts with lipophilic hydroperoxides such as methyl linoleate hydroperoxide in human histiocytic lymphoma U937 cells, shows no reactivity toward hydrogen peroxide (H₂O₂), and its fluorescence response changes linearly with increasing levels of methyl linoleate hydroperoxide^[3].
Diphenyl-1-pyrenylphosphine (167 μM; 5 min pre-incubation, measurement 1-24 h post-treatment) detects time- and dose-dependent endogenous lipid hydroperoxide production in human histiocytic lymphoma U937 cells induced by AAPH, serum deprivation, hydrogen peroxide, nitric oxide and diethyl maleate, and its fluorescence enhancement is inhibited by vitamin E^[3].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

386.42

C₂₈H₁₉P

110231-30-6

Solid

Off-white to light yellow

380

351

P(C1=CC=CC=C1)(C2=CC=CC=C2)C3=C(C4=C56)C=CC6=CC=CC5=CC=C4C=C3

Room temperature in continental US; may vary elsewhere.

4°C, protect from light

*In solvent : -80°C, 6 months; -20°C, 1 month (protect from light)

* Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month (protect from light). When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.

• [1]. Xing C, et al. Diphenyl-1-pyrenylphosphine: photo-triggered AIE/ACQ transition with remarkable third-order nonlinear optical signal change. Chem Commun (Camb). 2020;56(30):4220-4223.  [Content Brief]

  [2]. Okimotoa Y, et al. A novel fluorescent probe diphenyl-1-pyrenylphosphine to follow lipid peroxidation in cell membranes. FEBS Lett. 2000;474(2-3):137-140.

  [3]. Takahashi M, et al. Estimation of lipid peroxidation of live cells using a fluorescent probe, diphenyl-1-pyrenylphosphine. Free Radic Biol Med. 2001;31(2):164-174.