Propionyl

Weber G, Farris FJ (1979) Synthesis and spectral properties of a hydrophobic fluorescent probe 6-propionyl-2-(dimethylamino)naphthalene. Biochemistry 18 3075-3078... 

Catalan J, Perez P, Laynez J, Garcia-Bianco F (1991) Analysis of the solvent effect on the photophysics properties of 6-propionyl-2-(dimethylamino)naphthalene (PRODAN). J Fluor-esc 4 215-223... 

Abbreviations PRODAN 6-propionyl-2-(dimethylamino)naphthalene DENS 6-diethylaminonaphthalene-l-sulfonic acid. 

Weber G. and Farris F. J. (1979) Synthesis and Spectral Properties of a Hydrophobic Fluorescent Probe 6-Propionyl-2-(Dimethylamino)naphthalene, Biochemistry 18, 3075-3078. 

SFC grade C02 was purchased from Scott Specialty Gases. 6-propionyl-2-dimethylaminonaphthalene (PRODAN) was obtained from Molecular Probes. HPLC grade CH3OH and CH3CN were from Aldrich, and all reagents were used as received. 

Here, we summarize a recent study we have done on the effect of the environment on the electronic absorption and emission of 6-Propionyl-2-(A,A-dimethyl)aminona-phthalene (PRODAN) [8]. This system has widely been used as a fluorescence probe since it was introduced by Weber and Farris [31], The effect of polar solvents on the absorption and more effectively, on the fluorescence spectra of PRODAN is large,... 

Another example of intramolecular CT complex formation is provided by trans-4-dimethvlamino-4 -(1-oxobutvl)stilbene Solvent effects on the spectrum give a value of 22D for the excited state dipole moment. The effect of electric field on the fluorescence of 4-(9-anthry1)-N.N.-2.3,5,G-hexamethy1-aniline shows this compound forms an excited state whose dipole moment does not change with solvent . Chiral discrimination in exciplex formation between 1-dipyrenylamine and chiral amines is very weak . In the probe molecule PRODAN (6-propionyl)-2-(dimethylamino)—naphthalene the initially formed excited state converts to a lower CT state as directly evidenced by time-resolved spectra in n-butanol. Rate constants for intramolecular electron transfer have been measured in both singlet and triplet states of covalently porphyrin-amide-quinone molecules . Intramolecular excimer formation occurs during the lifetime of the excited state of bis-(naphthalene)hydrazides which are used as photochemical deactivators of metals in polyethylene . ... 

To illustrate the capabilities of the system shown in Fig. 16.12, we present new, previously unpublished results from our laboratory. In Fig. 16.13, we illustrate results for three fluorescent probe molecules (pyrene, DCM [4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran], and PRODAN [6-propionyl-2-(/V,/V-dimethylamino)naphthalene]) that were doped within a series of PFFA/Pluronic P104 BP blends. In the initial experiments, 16 BP formulations were prepared manually using micropipettes, while subsequent experiments utilized the ALHS to prepare 21 BP formulations. These formulations were spun cast into thin films employing quartz microscope slides as substrates. To characterize the local microenvironment surrounding each probe within a given formulation, steady-state fluorescence measurements using a conventional spectrofluorometer were performed. 

The retardation of the TICT process inside the water pool of the microemulsion compared to ordinary water is ascribed to the lower static polarity of the water pool compared to bulk water. The polarity or t(30) of the pool is obtained from the observed rate of HCT and by comparing them with the values obtained in homogeneous solutions. Karukstis et al. analyzed the emission spectra of 6-propionyl-2-(dimethyl-amino)-naphthalene (PRODAN) in microemulsions and showed that the PRODAN molecules at different sites within the microemulsions exhibit different emission spectra [226]. More recently, using picosecond total internal reflection, Bessho et al. [227] determined the emission lifetime of ANS at the water-heptane interface. They observed a nanosecond component in the decay of ANS at the water-heptane interface, indicating that the interface is considerably less polar than bulk water. 

Tables 2.1 and 2.2 give two examples concerning the positions of the absorption and emission of the fluorescence probes l-anilino-8-naphthalene sulfonate and 6-propionyl-2-(dimethylamino)naphthalene or PRODAN with the solvent. We can notice that for both fluorophores, the Stokes shift decreases with the decrease of the polarity of the solvent.

Figure 6.28. Qivge sepuition In the excited state of Prod an 6-propionyl-2-

F re 6.21 Solvent-polarity effect on fluorescence emission spectrum. Ruorescence emission spectrum of 6-propionyl-2-(dimethylamino)naphthalene (PRODAN) in various solvents. From left (o right cyclohexane, chlorobenzene, dimethylformamide, ethanol, water. See text From G. Weber and F.J. Fanis. Biochemistry 18 (1979) 3075. 

Preparation by alkaline hydrolysis of 6-propionyl-2-(3W)-benzoxazolinone with boiling 10% aqueous sodium hydroxide solution for 4 h (90-100%) [6913,6920]. 

Hydroxy-2-oxo-6-propionyl-2//-chromene-3-carboxylic acid ethyl ester 5-Hydroxy-6-propionylcoumarin-3-carboxylic acid ethyl ester... 

Pronapox. l-(l-Hydroxy-2-naphthalenyl)-l-propanone Oxime, 1965 Propioguaiacone. 1 -(4-Hydroxy-3-methoxyphenyl)- -propanone, 1814 6-Propionyl-2,5-dihydroxydiphenyl. 1 -(3,6-Dihydroxy[ 1,1 -biphenyl ]-2-yl)-l-propanone, 1921... 

CE Bunker, TL Bowen, Y-P Sun. A photophysical study of molecular probe 6-propionyl-2-(lV,lV-dimethylamino)-naphthalene (PRODAN) in aqueous and non-aqueous solutions. Photochem Photobiol 58 499, 1993. 

A recent study reports the solvation dynamics of coumarin 153 and 6-propionyl-2-dimethylaminon-aphthalene (PRODAN) in [emim][BF4] and [bmim] [BF4]. The fluorescence decay profiles showed biphasic solvation dynamics as was observed for molten tetraalkylammonium salts.- The results were interpreted as indicating a short-lived component resulting from the motion of the anion, followed by a longer-lived component resulting from the motion of both the anion and the cation. In the same papers, estimates of the value of (30) were made for these solvents based on comparisons of the values for each probe molecule in conventional solvents. The values obtained (48.9 from coumarin 153 and 47.1 kcal mol" from PRODAN for [bmim][BF4]) were somewhat lower than those measured directly using Reichardt s dye.- ... 

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