Prodan (dye)

[7] Being a push-pull dye, Prodan has a large excited-state dipole moment and consequently high sensibility to the polarity of its environment (solvent or cell membrane, including the physical state of surrounding phospholipids).

Excited-state relaxation of prodan is sensitive to whether the linkage between phospholipid hydrocarbon tails and the glycerol backbone is of ether or ester type.

[8] Absorption of Prodan lies in the UV range (361 nm in methanol),[3] but two-photon excitation techniques have been successfully applied.

[7] Cyclic voltammetry shows a reversible reduction peak at —1.85 V in acetonitrile and a quasi-reversible one at —0.88 in aqueous buffer (pH 7.3) (vs. NHE).

[8] Photostability of Prodan and Laurdan in low-polaritry environments is limited due to undergoing an intersystem crossing in the excited state, with subsequent reactions with triplet oxygen (this also diminishes its quantum yield, which is 0.95 in ethanol but only 0.03 in cyclohexane).

The structural formula for the naphthalene dye Prodan