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Synchronous Fluorescence Spectroscopic Study Of Spectrochimica Acta Part A 79 (2011) 1034–1041 Contents lists available at ScienceDirect Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy jou rnal homepage: www.elsevier.com/locate/saa Synchronous fluorescence spectroscopic study of solvatochromic curcumin dye ∗ Digambara Patra , Christelle Barakat Department of Chemistry, Faculty of Arts and Sciences, American University of Beirut, P.O. Box 11-0236, Riad El Solh, Beirut 1107-2020, Lebanon a r t i c l e i n f o a b s t r a c t Article history: Curcumin, the main yellow bioactive component of turmeric, has recently acquired attention by chemists Received 1 July 2010 due its wide range of potential biological applications as an antioxidant, an anti-inflammatory, and an Accepted 13 April 2011 anti-carcinogenic agent. This molecule fluoresces weakly and poorly soluble in water. In this detailed study of curcumin in thirteen different solvents, both the absorption and fluorescence spectra of curcumin Keywords: was found to be broad, however, a narrower and simple synchronous fluorescence spectrum of curcumin Curcumin was obtained at = 10–20 nm. Lippert–Mataga plot of curcumin in different solvents illustrated two Solvent polarity E sets of linearity which is consistent with the plot of Stokes’ shift vs. the 30. When Stokes’s shift in SFS T wavenumber scale was replaced by synchronous fluorescence maximum in nanometer scale, the solvent max E polarity dependency measured by SFS vs. Lippert–Mataga plot or T30 values offered similar trends as max measured via Stokes’ shift for protic and aprotic solvents for curcumin. Better linear correlation of SFS vs. ␲ max max * scale of solvent polarity was found compared to abs or em or Stokes’ shift measurements. In Stokes’ shift measurement both absorption/excitation as well as emission (fluorescence) spectra are required to compute the Stokes’ shift in wavenumber scale, but measurement could be done in a very fast and simple way by taking a single scan of SFS avoiding calculation and obtain information about polarity of the solvent. Curcumin decay properties in all the solvents could be fitted well to a double-exponential decay function. © 2011 Elsevier B.V. All rights reserved. 1. Introduction absorbs in the visible region and gives fluorescence with low quan- tum yield. Emission properties highly depend on the polarity of Curcumin, 1,7-bis(4-hydroxy-3-methoxyphenyl)-1,6- its environment [17]. Its photochemistry, including reactions with heptadiene-3,5-dione, is the main yellow bioactive component of oxygen, depends on the specific microenvironment of the molecule, turmeric (Curcuma longa), a perennial plant of the ginger family such as polar or non-polar and protic or aprotic solvents. Cur- (Zingiberaceae), which is native to tropical South Asia [1]. It is cumin is highly soluble in polar organic compounds but is slightly extensively used as a spice, food preservative and coloring agent. soluble in aliphatic or alicyclic organic solvents like hexane and It is a non-toxic, highly promising natural antioxidant compound cyclohexane. having a wide range of biological applications. It is anticipated that In conventional fluorescence, an emission spectrum is obtained curcumin may find applications as a novel drug in the near future by scanning the emission monochromator at various emission to control various diseases, including inflammatory disorders, wavelengths, em, at a particular excitation wavelength, ex, and carcinogenesis and oxidative stress-induced pathogenesis [1–4]. an excitation spectrum is obtained by scanning the excitation Curcumin has drawn intense interest recently due to its potential monochromator at various excitation wavelengths keeping the pharmaceutical importance [5–16]. emission monochromator constant at a particular wavelength. The Curcumin has two aromatic rings with phenolic OH groups con- other possibility is to scan both the monochromators simultane- ␣ ␤ ␤ nected by an , -unsaturated- -diketone (as given in Scheme 1). ously, which is called synchronous fluorescence scan/spectroscopy I The ␤-diketone structure undergoes keto–enol tautomerism in (SFS). Synchronous fluorescence intensity ( s) is directly related to c solutions [17]. The relative contributions of the keto and enolic tau- the concentration of the analyte sample ( ) as [22] tomers as well as their cis or trans form depend on factors such I s = Kcb Ex(ex) Em(ex + ); as solvent characteristics, temperature, polarity and substitution or, Is = Kcb Ex(em − ) Em(em); on curcumin [17–19]. However, at room temperature, the enolic form of diketones is in general predominant [19–21]. Curcumin where Ex is the excitation wave function at a given wavelength; Em is the emission wave function at a given wavelength; b is the thickness of the sample; K is the instrumental geometry and ∗ related parameters. SFS has been successfully used for various spec- Corresponding author. Tel.: +9611350 000x3985; fax: +9611365 217. E-mail addresses: [email protected], [email protected] (D. Patra). troscopic and spectrometric applications [23–27]. In this paper, 1386-1425/$ – see front matter © 2011 Elsevier B.V. All rights reserved. doi:10.1016/j.saa.2011.04.016 D. Patra, C. Barakat / Spectrochimica Acta Part A 79 (2011) 1034–1041 1035 HO OH+ H3CO OCH3 HO HO Protonated Form HO OH H3CO OCH3 O HO Neutral Form HO OH H3 CO OCH3 O O- Deprotonated Form-I HO O- H3 CO OCH3 O O- Deprotonated Form-II -O O- H3 CO OCH3 O O- Deprotonated Form-III Scheme 1. Protonated, neutral and deprotonated form of curcumin. the behavior of curcumin in different solvents is investigated in dissolved in spectroscopic grade dichloromethane (Acros Organ- detailed by synchronous fluorescence spectroscopy and compared ics). A desired amount of the stock sample was taken in a vial and with conventional fluorescence measurements. the solvent, dichloromethane, was evaporated by gentle heating. Final sample solution was prepared by adding required amount of desired solvent into the same vial. Cyclohexane, ethanol, hexane, 2. Materials and methods dichloromethane (DCM), 1,2-dichlorobenzene (DCB), 1,4-dioxane, 2.1. tetrahydrofuran (THF), methanol, acetonitrile, n-butyronitrile Materials (nBN), dimethylsulfoxide (DMSO) and N,N-dimethylformamide (DMF) were of spectroscopy grade and obtained from Acros Organ- Curcumin was obtained from Acros Organics and used without ics. The solvents were used without further purification. further purification. To prepare the stock solution, curcumin was 1036 D. Patra, C. Barakat / Spectrochimica Acta Part A 79 (2011) 1034–1041 Fig. 1. Absorption spectra of curcumin in solvents of different polarity. The low intense spectra in water, DCM, DMSO and THF are separately highlighted. 2.2. Spectroscopic measurements 2.3. Lifetime measurements The absorption spectra in various solvents were recorded at The fluorescence lifetime measurements were done using a room temperature using a JASCO V-570 UV-VIS-NIR Spectropho- Jobin–Yvon–Horiba Fluorolog III time correlated single photon tometer. Fluorescence measurements were done on a JOBIN YVON counting fluorometer attached with a pulsed diode laser. A 405 nm Horiba Fluorolog 3 spectrofluorometer. The excitation source was a diode laser was used as excitation source. The detector used was 100 W xenon lamp. The detector used was R-928 operating at a volt- R-928 operating at a voltage of 950 V. The fluorescence decay was age of 950 V. The excitation and emission slits width were 5 nm. The acquired with a peak preset of 10,000 counts. The decay data was synchronous fluorescence spectra were measured at = 5 nm, analyzed using Data Analysis Software. 10 nm, 50 nm, 100 nm, 150 nm and 200 nm. = 10 nm was chosen for the analytical measurement because of its high sensitivity and 3. Results and discussion narrower spectrum in the synchronous fluorescence wavelength range 250–700 nm. The spectral data were collected using Fluo- Fig. 1 depicts the absorption spectra of curcumin recorded in roescence software and data analysis was made using OrginPro 6.0 different solvents. The absorption is well extended to the visible software. region in all solvents under study. Generally, curcumin showed a D. Patra, C. Barakat / Spectrochimica Acta Part A 79 (2011) 1034–1041 1037 Table 1 Absorption maxima, emission maxima and Stokes’ shift of curcumin in various A Acetonitrile solvents. 1.0 Excitation Spectra Cyclohexane Water Compound Solvents abs em Stokes’ DCB − − − Curcumin (max)/cm 1 (max)/cm 1 shift/cm 1 0.8 DCM Dioxane Curcumin Acetonitrile 23,923.45 19,723.87 4199.58 DMF DMSO Cyclohexane 24,509.80 22,883.30 1626.51 0.6 Ethanol Water 24,154.59 18,621.97 5532.62 Hexane DCB 23,640.66 20,120.72 3519.94 Methanol DCM 23,866.35 20,964.36 2901.99 0.4 N-Butyronitrile THF 1,4-Dioxane 23,752.97 20,833.33 2919.64 DMF 23,529.41 21,321.96 2207.45 DMSO 23,041.47 19,305.02 3736.46 0.2 Ethanol 23,696.68 19,011.41 4685.28 Fluorescence Intensity (a.u.) Hexane 24,630.54 22,779.04 1851.50 0.0 Methanol 23,696.68 18,726.59 4970.09 300 350 400 450 500 n-Butyronitrile 23,584.91 18,656.72 4928.19 THF 23,696.68 20,964.36 2732.32 Wavelength (nm) B 1.0 Curcumin Emission Spectra strong and intense absorption band in the 350–480 nm wavelength Acetonitrile region in all the investigated solvents. The spectra in hexane and Cyclohexane 0.8 Water cyclohexane are structured. A loss of the vibrational fine struc- DCB ture was observed on going to more polar solvents. In these two DCM Dioxane non-polar and non-interacting solvents the lowest energy 0–0 0.6 DMF absorption band is clearly seen around 400–410 nm. There is appre- DMSO Ethanol ciable change in the energy of transitions in the different solvents 0.4 Methanol suggesting that solvent stabilization of ground state species is sig- Hexane N-Butyronitrile nificant.
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