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Journal of Thermal Analysis andCalorimetryAn International Forum for ThermalStudies ISSN 1388-6150Volume 110Number 3 J Therm Anal Calorim (2012)110:1333-1339DOI 10.1007/s10973-011-2121-5

Growth of <201> 8-hydroxyquinolineorganic crystal by Czochralski method andits characterizations

K. Aravinth, G. Anandha Babu &P. Ramasamy

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Growth of <201> 8-hydroxyquinoline organic crystalby Czochralski method and its characterizations

K. Aravinth • G. Anandha Babu • P. Ramasamy

Received: 17 September 2011 / Accepted: 24 November 2011 / Published online: 9 December 2011

� Akademiai Kiado, Budapest, Hungary 2011

Abstract In this study, 8-Hydroxyquinoline (8HQ) single

crystal has been successfully grown by Czochralski

method. The unit cell parameters of 8HQ single crystal

were confirmed by single crystal X-ray diffraction analysis.

The crystalline perfection of grown crystal has been

analyzed by high-resolution X-ray diffractometry. Fourier

transform infrared spectral studies have been performed to

identify the functional groups. The UV–Vis-NIR studies

show that the grown 8HQ crystal’s cutoff wavelength is

around 390 nm. The thermal property of the grown crystal

was studied by thermogravimetric and differential thermal

analysis. The laser damage threshold value of the grown

crystal was measured at multiple-shot mode using Nd:YAG

laser. The dielectric measurements were carried out to

determine the dielectric behavior for the crystal. The SHG

efficiency of 8HQ is 0.8 times that of KDP.

Keywords Optical materials � Organic compounds �Crystal growth � X-ray diffraction

Introduction

Quinolines are interesting molecules which have enhanced

non-centrosymmetry due to their lack of rotational sym-

metry. In the molecular design of new nonlinear optical

(NLO) materials based on quinoline, the pyridine ring can

function as an acceptor group and the benzene ring as

the donor. The optical nonlinearities of this class of

compounds can be improved by increasing the acceptor

character of the pyridine ring and/or increasing the donor

character of the benzene ring. 8HQ is an organic compound

with the formula C9H7NO. It is a derivative of heterocycle

quinoline by the placement of an OH group on carbon

number 8. 8HQ is a conjugated system and, at the same

time, a bifunctional hydrogen-bonding molecule, which in

protic solvents simultaneously acts as an H-donor at the

O–H group and as an H-acceptor at the N atom [1–5]. 8HQ

and its derivatives are widely used as chelating reagents in

analytical chemistry and radiochemistry for metal ion

extraction and fluorometric determination. 8HQ is a non-

hygroscopic organic material. Roychowdhury et al. repor-

ted that 8HQ crystal has an orthorhombic crystal system

with space group Fdd2 and cell parameters: a = 29.18 A;

b = 25.36 A; and c = 3.91 A [6]. The same crystal was

grown using the solution growth method by Vijayan et al.

[7] who reported that the crystal has an orthorhombic

crystal system with space group Fdd2 and cell parameters

same as reported by Roychowdhury et al. The same crystal

was grown using the solution growth method by Krish-

nakumar et al. who reported that the crystal has a mono-

clinic system with space group P21/m and cell parameters:

a = 3.862 A; b = 25.06 A; c = 14.515 A; and b =

97.58� [8]. The same crystal was also grown using the

solution growth method by Rajasekaran et al. who reported

that the crystal has SHG efficiency roughly 4.28 times that

of KDP [9]. Other authors [6, 8] have reported two dif-

ferent space groups and different unit cell dimensions.

Hence, we undertook the growth and characterization of

8HQ organic molecular NLO crystals from the melt using

Czochralski method. The grown crystals were character-

ized by single crystal X-ray diffraction to estimate the

lattice parameter values. The obtained lattice parameters

are a = 3.85 A, b = 24.93 A, c = 28.72 A, and V =

2754 A3. The grown 8HQ crystal belongs to orthorhombic

K. Aravinth � G. Anandha Babu (&) � P. Ramasamy

Centre for Crystal Growth, SSN College of Engineering,

Kalavakkam 603110, Tamilnadu, India

e-mail: anandcgc@gmail.com

123

J Therm Anal Calorim (2012) 110:1333–1339

DOI 10.1007/s10973-011-2121-5

Author's personal copy

crystal system with non-centrosymmetric space group

Fdd2. The observed unit cell parameters are in good

agreement with the previously reported values [6, 7].

In recent years, NLO materials play a major role in fast

developing optical devices. Organic materials for applica-

tions in nonlinear optics are interesting, because some

materials have shown extremely high nonlinearities, large

optical susceptibilities, frequency conversion, and ultrafast

response times. Some of the organic molecules which

exhibit high optical nonlinearity have been reported [10–13].

Organic molecules containing conjugate system have some

advantages over inorganic materials because of the possi-

bility of highly enhanced electronic NLO polarization

responses. The basic structure of organic NLO materials is

based on the p bond system [14]; due to the overlap of porbitals, delocalization of electronic charge distribution

leads to a high mobility of the electron density. Functioning

of both ends of the p bond system with appropriate electron-

donor and -acceptor groups can enhance the asymmetric

electronic distribution in either or both ground and excited

states, leading to an increased optical nonlinearity [15]. The

grown 8HQ crystals were also characterized by carrying out

Fourier transform infrared (FTIR), high-resolution X-ray

diffractometry (HRXRD), UV–Vis-NIR, thermal, dielec-

trics, laser damage threshold, and second harmonic genera-

tion (SHG) analyses.

Experimental procedure

Starting material 8-HQ was obtained from Lobo chemical

(GR grade). 8-HQ material (100 g) was filled in a cylin-

drical shape glass crucible having the size of 60-mm ID

and 110-mm length. The growth furnace is constructed

from borosilicate glass, making it easy to see the crystal at

all the stages of the growth. The source material filled in

the crucible was placed inside a kanthal ribbon-wound-

resistive heated furnace. Commercially bought temperature

controller with an accuracy of ±0.1 �C was employed to

control the temperature of the furnace. The temperature

was increased from room temperature to 80 �C. The tem-

perature of 2 �C higher than the melting point of 8HQ was

required initially to melt. Then, the temperature was

maintained for about 3 h to allow homogeneity. Then, the

temperature was decreased to 79 �C, which was slightly

higher than the melting point. In the mean time, the seed

was lowered to a position of 1 mm above the melt and left

for 10 min to attain the thermal equilibrium. The seed

orientation was \201[; a rotation rate of 3 rpm was

employed. The axial temperature gradient was 3 �C/cm

during the growth process. It indicated that the temperature

was suitable for seeding if the seed did not melt. Then, the

temperature was decreased to the melting point (about

78 �C) when the seed diameter was about 3 mm. Then, the

seed was slowly pulled up at a rate of 1.5 mm/h. The

growth rate was lowered to 1.2 mm/h, while the tempera-

ture was decreased at a rate of 1 �C/h after seeding. It took

about 3 h for the crystal to grow from a diameter in the

range of 3–8 mm. Finally, the crystal was grown at the

8-mm diameter. The rotation rate was still 3 rpm. When

growth run was completed, the grown crystal was detached

from the melt and the temperature of the chamber was

reduced slowly to room temperature. The grown crystal

having the diameter of 8 mm and length of 10 mm is

shown in the Fig. 1.

Characterization studies

Single crystal XRD studies

The single crystal XRD data of the grown 8HQ crystal was

obtained using Enraf–Nonius CAD4 single crystal X-ray

diffractometer with MoKa (k = 0.717073 A) radiation

to estimate the lattice parameter values. The grown 8HQ

crystal belongs to orthorhombic system with non-centro-

symmetric space group Fdd2. The obtained lattice param-

eters are a = 3.85 A, b = 24.93 A, c = 28.72 A, and

V = 2754 A3. The observed unit cell parameters are in

good agreement with the reported values [6, 7].

Fourier transform infrared spectroscopy

The FTIR spectra of 8HQ was recorded at room tempera-

ture in the region 400–4,000/cm at a resolution of ±4/cm

using Perkin–Elmer Fourier transform infrared Spectro-

photometer, using KBr pellets containing a fine 8HQ

powder obtained from the grown crystal, equipped with

TGS detector, KBr splitter, He–Ne Laser source and boxcar

apodization used for 250 averaged interferograms collected

Fig. 1 As grown 8HQ by Czochralski method

1334 K. Aravinth et al.

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for both the sample and the background. In this technique,

almost all functional groups in a molecule absorb charac-

teristically within a definite range of frequency [16].

The observed FT-IR spectrum is given in Fig. 2. The

Aromatic C–H stretching appears at 3,047/cm. The band at

1,578/cm is assigned to the C=C ring stretching vibration.

The C=N ring stretching vibration appears at 1,592/cm.

The O–H stretching vibration appears at 3,591/cm. The

C–O stretching vibration occurs at 1,285 and 1,222/cm.

The aromatic C–H plane bending appears at 1,173/cm. The

C–H out-of-plane bending occurs at 741 and 710/cm.

The peak at 1,433/cm is assigned to O–H plane bending.

The observed vibrational frequencies and their assignments

are listed in Table 1.

High-resolution X-ray diffraction studies

To evaluate the crystalline perfection of the specimen

crystals, HRXRD analysis was carried out. A multicrystal

X-ray diffractometer developed at National Physical Lab-

oratory (NPL), New Delhi [17] was used to record high-

resolution rocking or diffraction curves. In this system, a

fine focus (0.4 9 8 mm2; 2 kW Mo) X-ray source ener-

gized by a well-stabilized Philips X-ray generator (PW

1743) was employed. The well-collimated and monochro-

mated MoKa1 beam obtained from the three monochro-

mator Si crystals set in dispersive (?, -, -) configuration

has been used as the exploring X-ray beam. This arrange-

ment improves the spectral purity (Dk/k � 10-5) of the

MoKa1 beam. The divergence of the exploring beam in the

horizontal plane (plane of diffraction) was estimated to be

�3 arc s. The specimen crystal is aligned in the (?, -, -,

?) configuration. Owing to dispersive configuration of the

third monochromator crystal with respect to the 2nd

monochromator, the spectral quality of the diffracted beam

emerging from the 3rd monochromator is highly perfect

(Dk/k * 10-5; horizontal divergence �3 arc s), and

hence, though the lattice constant of the monochromator

crystal and the specimen are different, the unwanted

experimental dispersion broadening in the diffraction curve

of the specimen crystal [DFWHM = Dk/k(tanhM-tanhS);

hM and hS are the Bragg diffraction angles of monochro-

mator and the specimen crystals] is insignificant. The

advantage of dispersion configuration (?, -, -) over the

non-dispersive configuration (?, -, ?) of monochromators

is well described in a previous article [18]. The specimen

can be rotated about a vertical axis, which is perpendicular

to the plane of diffraction, with minimum angular interval

of 0.4 arc s. The diffracted intensity is measured by means

of a scintillation counter. The DC was recorded by

changing the glancing angle (angle between the incident

X-ray beam and the surface of the specimen) around the

Bragg diffraction peak position hB (zero taken as reference

point) starting from a suitable arbitrary glancing angle (h).

The detector was kept at the same angular position 2hB

with wide opening for its slit, the so-called x scan [19].

The omega scan is very appropriate to record the short-

range-order scattering caused by the defects or by the

scattering from local Bragg diffractions from agglomerated

point defects or due to low-angle and very-low-angle

structural grain boundaries [20]. Before recording the dif-

fraction curve, to remove the non-crystallized solute atoms

which remained on the surface of the crystal and also to

ensure the surface planarity, the specimens were first lap-

ped and chemically etched in a non-preferential etchant of

water and acetone mixture in 1:2 volume ratio.

Figure 3 shows the DC recorded for a typical 8HQ

specimen crystal using (321) diffracting planes in sym-

metrical Bragg geometry under identical experimental

conditions. As seen in the Fig. 3, the curve is not having a

single diffraction peak. The solid line, which follows well

with the experimental points (filled circles), is the convo-

luted curve of two peaks using the Lorentzian fit. The

additional peak depicts an internal structural low angle (tilt

angle C1 arc min but less than a deg.) boundary tilt angle

4000 3500 3000 2500 2000 1500 1000 500

0

20

40

60

80

100

Wavenumber/cm

Tra

nsm

issi

on/%

3591

3047

1578

1592

1222

1285

1433 11

73

780 74

171

0

Fig. 2 FTIR spectrum of 8HQ

Table 1 FT-IR spectral data of 8HQ

Wave number/cm-1 Assignments

3,591 O–H stretching vibration

3,047 Aromatic C–H stretching vibration

1592 C=N ring stretching vibration

1578 C=C ring stretching vibration

1433 O–H plane bending

1285 C–O stretching vibration

1173 C–H plane bending

780 O–H out of the plane bending

741 C–H out of the plane bending

Growth of \201[ 8-hydroxyquinoline organic crystal 1335

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of which (misorientation angle between the two crystalline

regions on both sides of the structural grain boundary) is

96 arc s from its adjoining region. The full width at half

maximum (FWHM) of the main peak and the low angle

boundary are, respectively, 42 and 306 arc s. The FWHM

of the grain of low-angle boundary is quite high showing

that this part of the crystal contains mosaic blocks miso-

riented to each other up to few tens of arc s. Though the

crystal contains a low-angle boundary, the low angular

spread of *800 arc s of the DC indicates that the quality

of the crystal is moderately good. It may be mentioned here

that such a low-angle boundary could be detected with

well-resolved peak in the diffraction curve only because of

the high resolution of the multicrystal X-ray diffractometer

used in the present studies. Such defects may not influence

much on the NLO properties. However, a quantitative

analysis of such unavoidable defects is of great importance,

particularly in case of phase-matching applications as

explained the article of another study [21].

Optical studies

Optical transmission spectrum of the grown 8HQ single

crystal was recorded in the wavelength region from 200 to

1,100 nm using Perkin–Elmer Lambda 35 UV–Vis Spec-

trophotometer. The grown 8HQ single crystal was cut and

polished, and the good transparent single crystal with

3-mm thickness in plate \201[ was used for this study.

The recorded spectrum is shown in Fig. 4. 8HQ crystal

presents a cut off wavelength at 390 nm.

Thermal analysis

Thermogravimetric (TG) and differential thermal analyses

(DTA) of the 8HQ single crystal were carried out using

NETZSCH STA 409 thermal analyser. An alumina cruci-

ble was used for heating the sample and analyses were

carried out in an atmosphere of nitrogen at a heating rate of

10 �C/min in the temperature range of 30–650 �C. The

result obtained from TG and DTA thermal studies are as

shown in Fig. 5. In DTA curve, the endothermic peak

observed at 78 �C is assigned to the melting point of the

grown crystal. The second endothermic peak around

232 �C may possibly be due to some complex formation.

The compound starts to decompose after 113 �C. There is a

weight loss between 113 and 236 �C. There is no phase

transition or decomposition before the melting point.

Dielectric studies

Dielectric properties are correlated with the electro-optic

property of the crystals [22]. Highly transparent crystal

–400 –200 0 200 4000

25

50

75

100

125D

iffr

acte

d X

-ray

inte

nsity

/c/s

Glancing angle/arc s

96″MoKα1

(+,−,−,+)

306″

42″

Fig. 3 Diffraction curve recorded for 8HQ single crystal for (321)

diffracting planes

200 400 600 800 1000 1200–5

0

5

10

15

20

25

30

35

Tra

nsm

issi

on/%

Wavelength/nm

Fig. 4 UV–Vis-NIR spectrum of 8HQ single crystal

0 100 200 300 400 500 600 700

0

2

4

6

8

10 DTA Weight/%

Temperature/°C

Mic

rovo

lts e

xodo

wn/

µV

78 °C

232 °C

0

20

40

60

80

100

Wei

ght/%

Fig. 5 TG/DTA curves of 8HQ

1336 K. Aravinth et al.

123

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sample of size 7 9 7 9 2 mm3 without any visible defects

was used for the dielectric measurements. The opposite

faces were polished and coated with graphite to obtain a

good conductivity surface layer. The capacitance and

dielectric loss factor were measured by the conventional

plate capacitor method with frequency range (100 Hz–

1 MHz) using Aglient 4284-A LCR meter at the range of

40–60 �C. The observations were made while cooling the

sample. Air capacitance (Cair) was also measured.

The dielectric constant of the 8HQ crystal was measured

as a function of frequency at different temperatures (40, 45,

50, 55, and 60 �C). The variations of dielectric constant

with the frequency at different temperatures is shown in the

Fig. 6. It is deduced that the dielectric constant is relatively

high at lower frequencies and decreases as the frequency

increases. The dielectric constant of materials is due to the

contribution of electronic, ionic, orientational, and space

charge polarizations which depend on the frequencies. At

low frequencies, all these polarizations are active [23]. The

dielectric constant of 8HQ crystal at 60 �C is 6.61, and this

value decreases to 3.61 at 40 �C for 100 Hz. The dielectric

constant is relatively high in the lower frequency and

almost saturated at 1,000 kHz.

Figure 7 shows the plot between the frequency and

dielectric loss at various temperatures. It is observed from

the plot that the dielectric loss decreases as the frequency

increases. The higher values of the dielectric loss at low

frequencies originate from space charge polarization. The

low dielectric loss value at higher frequencies indicates that

the grown 8HQ crystal contains minimum defects.

Laser damage threshold measurements

Optical damage in NLO material may severely affect the

performance of high-power laser systems as well as the

efficiency of the optical devices based on nonlinear pro-

cesses. Hence, high laser damage threshold is a significant

parameter for NLO crystal. The laser-induced damage

studies have been carried out for the Czochralski method-

grown 8HQ single crystal. Then, the samples were polished

using Al2O3 just before the laser damage threshold

measurements. A Q-switched Nd: YAG laser operating at

1,064-nm radiation was used. The laser was operated at the

repetition rate of 5 Hz with the pulse duration of 30 ns. For

the laser damage threshold measurement, 1-mm-diameter

beam was focused on the samples with a 30-cm-focal length

lens. The pulse energy of each shot was measured by using

combination of phototube and oscilloscope. The samples are

irradiated at different spots on the same plane at a similar

experimental condition, and the damage pattern was

observed using an optical microscope. The observed dam-

ages of the crystals are shown in Fig. 8. The surface damage

threshold of the crystal was calculated using the expression

Power density Pdð Þ ¼ E= spr2

where E is the energy (mJ), s the pulse width (ns), and r the

radius of the spot (mm). A crack is observed after passing

2 3 4 5 61

2

3

4

5

6

7

Die

lect

ric

cons

tant

/εr

Log frequency/Hz

60 °C 55 °C 50 °C 45 °C 40 °C

Fig. 6 Variation of dielectric constant with frequency of 8HQ

2 3 4 5 6

0.0

0.2

0.4

0.6

0.8

1.0

Die

lect

ric

loss

Log frequency/Hz

60 °C 55 °C 50 °C 45 °C 40 °C

Fig. 7 Variations of dielectric loss with frequency of 8HQ

Fig. 8 Laser damage profile of 8HQ single crystal

Growth of \201[ 8-hydroxyquinoline organic crystal 1337

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75 mJ energy in 30 s. Multiple-shot surface laser damage

threshold of 8HQ was determined to be 0.88 GW/cm2 for

1,064-nm wavelength of Nd: YAG laser radiation.

SHG study

The SHG conversion efficiency of 8HQ was measured by

Kurtz powder techniques [24]. A Q-switched Nd: YAG

laser was used as light source. A laser beam of fundamental

wavelength 1,064 nm, 8 ns pulse width, with 10 Hz pulse

rate was made to fall normally on the sample cell. Second

harmonic radiation generated by the randomly oriented

microcrystals were focused by a lens and detected by the

photomultiplier tube. The energy per pulse of 1,064-nm

laser radiation attenuated using high-energy variable

attenuator is measured using an energy power meter which

is externally triggered by the Nd: YAG laser. The

conversion efficiency for SHG depends on power of the

fundamental beam, field-gain coefficient, size of the crys-

tal, and minimum beam waist. In present study, KDP

sample was used as the reference material, and output

power intensity of 8HQ has been found to be 0.8 times that

of KDP.

Conclusions

Single crystals of 8HQ were grown using the Czochralski

growth technique. The unit cell parameters of 8HQ were

confirmed by single crystal X-ray diffraction analysis.

The grown 8HQ crystal belongs to orthorhombic system

with non-centrosymmetric space group Fdd2. The crys-

talline perfection of the grown crystal is demonstrated as

observed by high-resolution X-ray diffraction studies.

FWHM value of the Czochralski method-grown 8HQ

crystal, which is obtained as 96 arc s, shows that the

crystalline perfection is moderately good. The functional

groups were confirmed by FTIR measurements. The UV–

Vis-NIR studies show that the grown 8HQ crystal’s cutoff

wavelength is around 390 nm. In the transmittance spec-

tra, it is evident that the 8HQ crystal has wide transpar-

ency range in the entire visible and NIR range. The

thermal behavior of the grown crystal was studied using

TG/DTA. 8HQ crystal decomposed at 113 �C. The

dielectric constant and dielectric loss studies of 8HQ

establish the normal behavior. Multiple-shot surface laser

damage threshold is determined to be 0.88 GW/cm2 at

1,064-nm laser radiation. The SHG efficiency of 8HQ is

0.8 times that of KDP.

Acknowledgements The authors are thankful to Dr. G. Bhagav-

annarayana, the National Physical Laboratory, New Delhi for

HRXRD studies.

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