(III) Acetylacetonate Derivatives by Solvothermal Method

Research Article: Open Access are credited. author andsource inanymedium,providedtheoriginal License, whichpermitsunrestricted use,distribution,andreproduction Copyright: Received: 82322759, Fax:+86-10-82322345, E-mail: Tel: +86-10- China, 100083, District, Beijing Haidian Road, of Geosciences,No.29Xueyuan University China Minerals andSolidWastes, Laboratory of Mineral Materials,Schoolof National Materials ScienceandTechnology, of Nonmetallic Utilization of Materials Key Laboratory Zhang, Beijing Yihe Lv and *Corresponding author:Fengzhu Introduction Mineral Materials,SchoolofMaterialsScienceandTechnology,ChinaUniversityGeosciences,Beijing, Beijing KeyLaboratoryofMaterialsUtilizationNonmetallicMineralsandSolidWastes,National Fengzhu Lv*,YiheZhang*,XueChenandYongMa acetonate DerivativesbySolvothermalMethod (III) Acetyl Gadolinium and Fluorescenceof Composition tion ofmultifunctionalmaterials,suchasmaterialswith modified to widen their application [6,7]. But prepara- rare earth β-diketonate complexes were studied and solution techniques[4,5].Sothefluorescenceofsome more efficientapproachtofabricateOLEDdevices by processable organic semiconductors and also provides vents highlyenhancestheirapplicationsinthesolution earth β-diketonatecomplexesincommonorganicsol- π-conjugated system.Goodsolubilityofsubstitutedrare which isdependent on theligand molecule with large complexes relatedtotheabsorptionefficiencyofligands, excitation [1-3].Theluminescenceintensityofrareearth ible andnear-infraredregionsunderUltraviolet(UV) lifetime, narrowbandwidthandlargeStokesshiftinvis- luminescent sensorsbenefitingfromtheirlongemission applications innovellightingdevices,opticalfibersand by Solvothermal Method.IntJOptPhotonic Eng 2:005 Citation: Generally, rareearthcomplexeshavemanypotential VIBGYOR March09,2017: Lv F, Zhang Y, Chen X, Ma Y (2017) Composition and Fluorescence of Gadolinium (III) Acetylacetonate Derivatives (III) Acetylacetonate ofGadolinium Fluorescence and X, MaY(2017)Composition Y, Chen Lv F,Zhang © 2017 LvF, article distributedunderthe termsoftheCreativeCommonsAttribution et al.Thisisanopen-access Gadolinium (III)acetylacetonatederivatives,Solvothermalmethod,Luminescence Keywords magnetic and with materials were hydrophobic fluorescent properties. products the So field. magnetic external toward ability responding and intensity fluorescent higher possessed °C 160 at produced product the Also acetylacetonate. (III) Gadolinium to compared fluorescence excitation and emission energy higher magnetic and properties of the products were studied fluorescence, in detail. The fluorescence showed the products possessed composition, The groups. -OH and acetylacetonate with complexes gadolinium method toproduce wastreatedbysolvothermal (III) acetylacetonate Gadolinium Abstract Accepted:July22,2017: [email protected] Published: 320 tion ofthehydrolyzedprecursor-surfactantaggregatesat sis ofGd-(AcAc) selectively preparedfromlow-temperature(90°C)hydroly- hydrolysis of acetylacetonate is limited. The products diphenyl etherwhichisawaterlacksystemwhere the hydrate wastreatedbysolvothermalmethodinabsolute earth acetylacetonate. organic solventandchangedfluorescencecomparedtorare posed samplesaswhichispreferredpossessingsolubilityin 13]. ColloidalcubicGd microelectronic, catalyticand biomedical applications [10- nanoparticles ofmetals,metalalloysandoxidesfor recently attractedmuchattentiontofabricatethinfilmsand is theprojectofresearchers[8,9]. fluorescence and magnetic properties, by simple method July24,2017 Engier Optics andPho Inter In thepresentworkGadolinium(III)acetylacetonate Thermal decomposition of metal acetylacetonates has Thermal decompositionofmetalacetylacetonateshas o ; [email protected] C [14].Butseldomreportsfocusonthepartialdecom- natiol Jur 3 andsubsequentinsituthermaldehydra- Lv etal.IntJOptPhotonicEng2017,2:005 2 O nal of 3 nanorings and nanoplates were nanoringsandnanoplateswere ISSN: 2631-5092 - Lv et al. Int J Opt Photonic Eng 2017, 2:005 ISSN: 2631-5092 | • Page 2 of 8 • were preferred possessing solubility in organic solvent different temperature for 2.0 h. After that the autoclave and changed fluorescence compared to rare each acety- was cooled to room temperature, the as-obtained yellow lacetonate as well as magnetic properties. So different suspension was mixed with an equal volume of acetone, kinds of Gadolinium (III) acetylacetonate derivatives and the formed precipitate was separated by centrifuga- were produced. The composition, fluorescence and mag- tion and washed with acetone. The final samples were netic properties were studied in detail. Under appropri- assigned as Gd-S-T, where T indicated the formed tem- ate preparation conditions, Gadolinium (III) acetylace- perature by solvothermal. Gd-S-160 was grounded and tonate derivatives with higher fluorescent intensity and calcinated at 450 °C for 10 h in air to give Gd-C-160. magnetic properties were produced. Afterwards, Gd-C-160 was furnace-cooled to room temperature, and grounded again into powder for measure- Experimental ment. Materials Characterization The raw material for synthesis of Gadolinium (III) Thermal Gravimetric Analysis (TGA) was measured acetylacetonate derivatives was gadolinium acetylace- on Perkin-Elmer TGA 7 with a heating rate of 20 °C/min tonate trihydrate (Gd(AcAc) ·3H O, MW = 508.62 g/ 3 2 ranging from 45 °C to 800 °C in air, on the same time mol), which was purchased from Beijing HWRK Chem- a NETZSCH STA 449F3 Thermo Gravimetric Analy- ical Co., Ltd.. Diphenyl ether was applied by Sinopharm ser was coupled, using a heated capillary at 190 °C, to a Chemical Reagent Beijing Co., Ltd. Other solvents were QMS 403 Mass Spectrometer (TGA-Ms) to identify the from Beijing Chemical factory. released gases during the thermal degradation of a ma- Preparation of Gadolinium (III) acetylacetonate terial. The Fourier Transform Infrared Spectra (FTIR) derivatives of the solid samples was obtained with a Perkin Elmer Spectrum 100 FT-IR spectrometer. KBr pellet was used In a typical synthesis for the derivatives of Gd(A- as background. The structure of the products was stud- cAc)3·3H2O, 1.5787 g (0.003 mol) of Gd(AcAc)3·3H2O ied by powder X-ray diffraction (Rigaku D/max-rA) was dispersed into 10.5 mL of absolute diphenyl ether equipped with Cu Kα (λ = 0.1542 nm) radiation at 40 kV to form a solution under magnetic stirring, which was and 30 mA. The surface morphology and the elemental poured into 25 ml teflon-lined autoclave and heated at distribution of the samples were probed with Scanning

1.0 Gd(AcAc) .3H O 0.55 3 2 (b) Gd(AcAc)3.3H2O (a) Gd-S-160 ) 0.50 Gd-S-220

Gd-S-160 C o

0.8 Gd-S-220 / 0.45 o / o ) ( 0.40 o

/ t o ( h 0.35 0.6 g t i h

e 0.30 g

i W e 0.25

0.4 . W v

i 0.20 r

e 0.15 D 0.2 0.10 0.05 0.0 0.00 100 200 300 400 500 600 700 800 200 300 400 500 600 700 800 Temperature (oC) o Temperature ( C) 1.0 (c) CO 0.8 2 ) o / o

( CO

0.6 t h g

i e 0.4 W

H2O 0.2 O2

0.0 100 200 300 400 500 600 700 800 o Temperature ( C)

Figure 1: TGA (a) and DTA (b) curves of Gd(AcAc)3·3H2O, Gd-S-160, and Gd-S-220, TGA-Ms of Gd-S-160 (c).

Electron Microscope (SEM, HITACHI S-4300) operated at an acceleration voltage of 5 kV. The zeta potential and (h) size distribution of the hybrid particles were measured 3415 1548 499 ) o

on Malvern Instruments Zetasizer Nano-ZS90. The Ul- / (g)

o 1441 ( traviolet-Visible (UV-vis) spectra were measured with e (f) UV6100 double beam spectrophotometer. Room tem- c n

a (e) perature excitation and emission spectra were charac- t t terized by F97 spectrofluorometer (Shanghai Lengguang i m (d) s

Technology Co., China) with a 150 W Xe lamp as the n a excitation source. The temperature-dependent lumi- r (c) T nescence properties were measured on the fluorescence (b) 3300 536 spectrophotometer (F-4600, HITACHI, Japan), which 1523 1391 (a) 1602 was equipped with a self-made heating attachment and a 1016 918 computer controlled electric furnace. The luminescence 4000 3500 3000 2500 2000 1500 1000 500 decay curve was obtained from a spectrofluorometer Wavenumber (cm-1) (HORIBA, JOBIN YVON FL3-21) with a 335 nm pulse Figure 2: FI-IR spectra of a) Gd(AcAc)3·3H2O; b) Gd-S-140; laser radiation (nano-LED) as the excitation source, and c) Gd-S-160; d) Gd-S-180; e) Gd-S-200; f) Gd-S-220; g) Gd- the pulse width of the laser was 12 ns. S-240 and h) Ga-S-260 prepared in 2 h.

Results and Discussion

To prepare derivatives of Gd(AcAc)3·3H2O by solvothermal method, TGA together with Differential Ther- 1065

) (d) o mal Analysis (DTA) were performed to determine the / o 863 ( 3409 decomposition temperature of Gd(AcAc) ·3H O. As 1531 537 3 2 e (c) 1411 c

shown in Figure 1a, the weight losses for all the samples n

a 3407 t

below 150 °C are assigned to the departure of adsorbed t water and comlexed water with gadolinium [15]. Gd(A- i 1550 1441 m (b) s cAc)3·3H2O exhibits complicated decomposition behav- n a ior due to more ligands in it. It shows one little and two r broad DTA peaks with shoulders between 190-350 °C T (a) and 350-500 °C (Figure 1b). So it is preferred, Gd(A- 495 cAc)3·3H2O derivatives may form around 200 °C where

Gd(AcAc)3·3H2O decomposes partially. 4000 3500 3000 2500 2000 1500 1000 500 Wavenumber (cm-1) Figure 2 shows the FT-IR spectra of the products prepared at around 200 °C. In the spectrum of Gd(A- Figure 3: FI-IR spectra of Gd-S-160 prepared in a) 2; b) 4; -1 c) 12 h and d) Gd-C-160. cAc)3·3H2O (Figure 2a), the peak at 1602 cm is asso- ciated with the enol-keto tautomers of the β-diketone corresponding to the C = O stretching vibration of keto. connecting Gd. As long then the reaction time from 2 h The peak at 1523 cm-1 is the C = C stretching vibration of to 12 h, the FT-IR spectra of Gd-S-160 (Figure 3) have no enol. The peaks at 1391 cm-1 and 1016 cm-1 are the vibra- obvious change indicating that acetylacetone groups are -1 stable in relative severe solvothermal process. In order tions of -CH3 [15,16]. The wide band at about 3300 cm to verify that acetylacetone groups are still in the formed is the vibration of crystallined water of Gd(AcAc)3·3H2O. The peak at 536 cm-1 is the vibration of a Gd-O stretching samples, Gd-S-160 is calcinated at 450 °C for 2 h to give absorption. While for the solvothermal samples (Figure Gd-C-160. Its FTIR spectrum (Figure 3e) shown the 2b-2h), the still appearing peak at 1016 cm-1 relating to peaks at 1548 cm-1 and 1441 cm-1 disappear and bands at 1504 cm-1, 1398 cm-1, 1096 and 863 cm-1 due to ν OC-O, the vibration of -CH3 confirms that some acetylacetone as 2- groups are still in the final samples although the solvo- νs C-O, p-CO3 appear, confirming the calcinated sample 2- thermal temperature is up to 260 °C (Figure 2h). The is Gd(OH)CO3 or (GdO2)CO3 [17]. So it is referred that -1 peaks at 1548 and 1441 cm are the C = O and C = C the solvothermal samples are Gd(OH)x(AcAc)3-x, where stretching vibration of β-diketone which left shift due x is between 0-3 and AcAc is the acetylacetonate group. to the substitution of one or two acetylacetone groups In order to clearly determine the composition of by OH in the solvothermal process [16]. The peak at the prepared samples, TGA and DTA of Gd-S-160 and -1 495 cm is the vibration of Gd-O-Gd. The broad peak at Gd-S-220 were measured (Figure 1). Gd-S-160 and Gd- -1 ~3415 cm is considered as structural hydroxyl groups S-220 all show one obvious degradation DTA peak be-

Citation: Lv F, Zhang Y, Chen X, Ma Y (2017) Composition and Fluorescence of Gadolinium (III) Acetylacetonate Derivatives by Solvothermal Method. Int J Opt Photonic Eng 2:005 Lv et al. Int J Opt Photonic Eng 2017, 2:005 ISSN: 2631-5092 | • Page 4 of 8 • tween 250-400 °C which corresponds to ~44% and 32% weight loss, respectively. If considering the sample is (f) Gd(OH) (AcAc)2 or Gd(OH)2(AcAc), its corresponding ) degradation weight loss would be 45% or 32%. That is the . (e) u . weight losses of Gd-S-160 and Gd-S-220 can well match a ( (d) y that of Gd(OH)(AcAc)2 and Gd(OH)2(AcAc). So the t i s

2 n radation products of Gd-S-160 are measured by TGA- I (b) MS (Figure 1c). Between 300-400 °C, small molecules (a) including CO, CO2, H2O are produced confirming the JPCDS 47-0579 (GdO )CO organic groups are preserved in Gd-S-160. In the DTA 2 3 curve of Gd-S-160 between 450-600 °C, one obvious 10 20 30 40 50 60 70 broad band appear while no degradation occur showing 2Theta (Degree) a phase change takes place which may be indexed as the Figure 4: XRD patterns of a) Gd(AcAc)3·3H2O; b) Gd-S- transition of Gd with 3 complex number to Gd2O3. 140; c) Gd-S-160; d) Gd-S-180; e) Gd-S-240 and h) Gd-S- 260 prepared in 2 h, and f) Gd-C-160 prepared in 10 h.

C Ka1 2

Gd La1 O Ka1 Figure 5: SEM of Gd-S-160 (a,b,c) and the C (d), Gd (e), O (f) dispersion on the particles.

Figure 4 shows the XRD patterns of Gd-S-T and Gd- C-160. New peaks appear between 10-15o compared Gd-S-160 to Gd(AcAc)3·3H2O with the increase of reaction tem- Gd-C-160

perature and reaction time. This is due to the substitu- ) o / o tion of acetylacetone by -OH with the hydrolysis. Sim- (

y ilar phenomenon was reported by hydrolysis of Gd(A- t i s cAc)3·3H2O in DMF [18]. The characteristic diffraction n e t peaks of Gd-C-160 can well match that of (GdO2)CO3 n (JPCDS-47-0579). These result confirms that in diphe- I nyl ether the trace water from structural water of Gd(A- cAc)·3H2O can cause Gd(AcAc)·3H2O hydrolyze to form

Gd(AcAc)x(OH)3-x where x is between 0 and 3. 10 100 1000 10000 The SEM and the element dispersions of the prepared Size (d.nm) Gd-S-160 are shown in Figure 5. In the magnetified pho- Figure 6: Particle dispersion of Gd-S-160 and Gd-C-160. tograph (Figure 5b), it can be seen that Gd-S-160 is in rod shape with some irregular particles, the scanning photos show that C, Gd and O uniformly dispersed on the parti- ) . u cle confirming the formation of Gd(AcAc)x(OH)3-x. . Gd(AcAc)3.3H2O a

( Gd-S-140

The particle sizes of Gd-S-160 and Gd-C-160 were y Gd-S-160 t i measured by Z potential and shown in Figure 6. The par- s Gd-S-200 n e ticle size of most of Gd-S-160 is 200-400 nm with little t n

I part being about 800 nm. While about 40% of Gd-C-450 n o is in the particle size of 200-500 nm, about 50% in 700- i t p

1200 nm, and about 10% in 1300-1600 nm. These data r o show that under suitable solvothermal conditions, the s b prepared Gd-S-T not only contain organic groups but A also have relative small particle size compared to general 200 300 400 500 600 700 solvothermal-calcination process. The interesting thing Wavelength (nm) is that no matter Gd-S-T or its calcinated products show Figure 7: UV-v is absorbance of S-Gd-T. positive surface charges. The Z potential of Gd-S-160 and Gd-C-160 are 42.1 mV and 34.9 mV. of 490 nm. Gd(AcAc)3·3H2O shows two absorbance, one Figure 7 shows the UV-v is absorbance of Gd(A- is between 320-370 nm, the other is between 370-450 nm * * cAc)3·3H2O and Gd-S-T. For Gd(AcAc)3·3H2O, only one attributed to π-π and n-π transitions of β-diketonate li- absorbant peak centered at 294 nm is observed which is gands [5]. While for Gd-S-140 and Gd-S-160, three peaks attributed to the π-π* transition of β-diketonate ligand are observed which are at 310-350, 350-375 and 375-450 [5]. Due to the forbidden of electron transition between nm. As emission exited under UV irradiation is aimed in ligands and Gd3+ which has stable electron arrangement, the present work, so emission fluorescence is excited by still only one peak is observed for Gd-S-140, but right 365 nm and the spectra are shown in Figure 8b. Gd(A- shifts to 308 nm indicating the π-π* transition of β-dike- cAc)3·3H2O shows one strong emission peak at 520 nm. tonate ligand becomes more easier and the conjugation While the emission of Gd-S-140 and Gd-S-160 left shift degree Gd with acetylacetone groups is weakened. For indicating that high energy luminescence is produced. Gd-S-160 and Gd-S-200, two absorbent peaks appear. Although the acetylacetone groups of Gd(AcAc)3·3H2O Except the absorbance at 308 nm, a peak at 275 nm due is more than Gd-S-160, but the emission peak of Gd-S- to the π-π* transition of β-diketonate due to the energy 160 is the highest. Just as shown in Figure 9 [19], as the match of ligands after substitution of acetylacetone by bound ability of -OH to electron is stronger than acetyl- OH groups. acetone group, substitution of some of the acetylacetone 3+ Generally speaking, rare earth organic complexes pro- group by -OH will result in weak interaction of Gd with duce intense emission peaks in visible and near-infrared the left acetylacetone groups of the prepared samples, regions under Ultraviolet (UV) excitation. For obtaining and thus the controlling ability of acetylacetone group to optimum emission spectra, the excitation wavelength electron is increased. So the energy between the ground for emission measurement is determined by excitation state and exited state in the prepared samples is highered spectrum measurement. Figure 8a is the excitation fluo- which results in emission of fluorescence with shorter rescence of Gd-S-T in ultraviolet region under emission wavelength compared to Gd-acetylacetonate [7,20]. As

Gd(AcAc) 3H O (a) (b) λ = 365 nm 3. 2 λ ex Gd-S-140 Gd(AcAc)3.3H2O em = 490 nm Gd-S-160

Gd-S-140 )

)

. Gd-S-180 . u u Gd-S-160 Gd-S-200 . . a a Gd-S-220 Gd-S-220 ( (

Gd-S-240 y y t t i i Gd-S-260 s s

Gd-S-280 n n e e t t n n I I

200 250 300 350 400 450 400 450 500 550 600 650 Wavelen gth (nm) Wavelength (nm) λ 30 oC S-Gd-160 ex = 365 nm (c) o (d) 50 C 75 oC curve t/ns )

o ) . 100 C . 1000 Gd-S-160 5.03 u u

. o 125 C . λ = 335 nm a ex a

( o (

λ 150 C em = 490 nm y y t t i i s s

n n e e 100 t t n n I I

400 450 500 550 600 650 700 0 20 40 60 80 100 Wavelength (nm) Time (ns) Figure 8: Excitation a) emission; b) fluorescence of Gd-S-T at room temperature and the temperature dependent fluorescence; c) and life time of; d) Gd-S-160.

σ * σ *

π* H C 3

H3C

π* fluorescence fluorescence H3C

H2O O H C CH hv 3 3 OH O O O O hv Gd

H2O H2O Gd O O O O H C O 3 CH H2O 3

CH3

CH CH 3 3 n n π π

σ σ

Figure 9: Energy stage schematic of Gd(AcAc)3·3H2O and their products. the temperature for preparation of Gd-S-T is higher than consumed and the emission strength of the derivatives 200 °C, the emission of the products becomes weak as is decreased, which is confirmed by fluorescent life time the amount of acetylacetone groups decrease. Figure 8c measurement. The life time of Gd-S-160 is only 5.03 ns. shows the temperature dependence of Gd-S-160. Gen- Short lifetime indicates short time of electrons in existed erally, the fluorescence of organic complex decreases state and more energy is consumed. With the increase with temperature. At higher temperature, the vibration of temperature up to 125 °C, the fluorescence of Gd-S- of electron in acetylacetone increases, so more energy is 160 decreases sharply and left shifts due to the weakened

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Citation: Lv F, Zhang Y, Chen X, Ma Y (2017) Composition and Fluorescence of Gadolinium (III) Acetylacetonate Derivatives by Solvothermal Method. Int J Opt Photonic Eng 2:005