34 9

2015. 9

JIEGOU HUAXUE
Chinese J. Struct. Chem.

Vol. 34, No. 9

13911398

Synthesis, Crystal Structure and Properties of Barium

Coordination Compound Based on
1,3,5-Benzenetricarboxylic Acid Ligand
WU Ganga QIN Cheng-Songa
WANG Xiao-Fengb
a

(College of Material and Chemical Engineering,

Chuzhou University, Chuzhou, Anhui 239012, China)

b

(College of Environmental Science, Xiaozhuang University, Nanjing 211171, China)

ABSTRACT

A new coordination polymer [Ba3(btc)2(H2O)8]2H2O (1, H3btc = 1,3,5-benzenetri-

carboxylic acid) has been synthesized and characterized by single-crystal X-ray diffraction,
elemental analysis and infrared spectroscopy analysis. All carboxylate oxygen atoms of btc3
participate in coordination with the central Ba(II) ions. The Ba(1) center is eight-coordinated with a
distorted square antiprismatic coordination geometry, while the Ba(2) ion is ten-coordinated with a
distorted dicapped square prism. Three carboxyl groups of the anion btc3- take 2-1:1 and 2-2 :1
coordination modes, respectively. The whole btc3- anion acts as a 6-bridge connecting six different
Ba(II) ions to form a 3D framework structure. Luminescent and thermal stable properties of
complex 1 were investigated.
Keywords: 1,3,5,-benzenetriarboxylic acid, crystal structure, barium;
DOI: 10.14102/j.cnki.0254-5861.2011-0678

benzenetricarboxylate is a versatile building block

INTRODUCTION

for the synthesis of functional metal organic frameIn last decades, the metal-organic frameworks
(MOFs) have attracted more and more attention not

works due to its polytopic carboxylate groups, high

symmetry and planar geometry[13-17].

only for their fascinating architectures and topolo-

On the other hand, alkali-earth-metal-containing

gies, but also for their potential applications, such as

coordination compounds have received considerable

luminescence, magnetism, gas storage and catalysis,

interest recently because of their ability to form

[1-4]

. Carboxylic acid, owing to its multifa-

bonds with oxygen donors, their large radii, high

rious species and various coordination modes, has

coordination numbers, various coordination modes,

been widely introduced to construct the metal

and potential applications of complexes in several

and so on

[5-7]

. A large number of

possible applications in luminescent and electronic

metal aromatic carboxylates have been reported as

devices[18]. In this article, a barium complex of

potential porous functional materials as catalysis,

1,3,5-benzenetricarboxylic acid was synthesized and

organic framework (MOFs)

[8-12]

separation, gas storage, etc

. Among them, 1,3,5-

its structure was characterized. The fluorescent and

Received 10 February 2015; accepted 15 April 2015 (CCDC 1046919)

This project was supported by the National Natural Science Foundation of China (41472047),
Science Research Starting Project of Chuzhou University (2014qd035) and Student Creative Project of Chuzhou University
Corresponding author. Wang Xiao-Feng, born in 1979, E-mail: wangxf0215@163.com

WU G. et al.: Synthesis, Crystal Structure and Properties of Barium

Coordination Compound Based on 1,3,5-Benzenetricarboxylic Acid Ligand

1392

No. 9

thermal stable properties of the complex were also

1102(w), 1024(w), 844(w), 764(s), 722(s).

investigated.

2. 3

Structure determination and refinement

A single crystal with dimensions of 0.32mm

EXPERIMENTAL

0.30mm 0.27mm was put on a Bruker Smart Apex

CCD diffractometer equipped with a graphite-mono-

2. 1

General procedures

chromatized MoK radiation ( = 0.71073 ) by

All reagents commercially available were of

using a - scan mode at 296(2) K. In the range of

reagent grade and used without further purification.

1.6127.45, a total of 10647 reflections were

Solvents were purified according to the standard

collected and 3050 were independent with Rint =

methods. The luminescent spectra for the solid

0.0944, of which 2803 were observed with I > 2(I).

samples were recorded at room temperature on

The structure was solved by direct methods using

CaryEclipse 300 spectrophotometer with a xenon arc

the SHELXS-97 program package and refined

lamp as the light source. In the measurements of the

against

F2

by

full-matrix

least-squares

with

[19, 20]

emission and excitation spectra, the pass width was

SHELXL-97

. All non-hydrogen atoms were

5.0 nm. C and H elemental analyses were carried out

refined anisotropically and hydrogen atoms located

on a Perkin-Elmer 240C elemental analyzer. IR

and refined isotropically. Complex 1 crystallizes in

spectra were recorded on a Nicolet 6700 FT-IR

monoclinic, space group P21/c with a = 12.6263(6),

spectrophotometer by using KBr pellet in the range

b = 16.0391(8), c = 6.8240(3) , = 91.136(2)o, Z =

of 4000 400 cm1. Powder X-ray diffraction

2, C18H26Ba3O22, Mr = 1006.41, Dc = 2.419 g/cm3,

patterns were performed with a Bruker D8

F(000) = 956, = 4.326 mm-1, the final R = 0.0422

ADVANCE X-ray diffractometer with Cu-K

and wR = 0.1066 (w = 1/[2(Fo2) + (0.0682P)2 +

radiation at 40 kV and 40 mA. Thermogravimetric

1.2752P], where P = (Fo2 + 2Fc2)/3) for all data, and

analyses (TGA) were carried out with a SDT Q600

S = 1.044. The selected bond lengths and bond

instrument under 100.0 mL/min flowing nitrogen

angles are listed in Table 1.

from room temperature to 600 at a heating rate of

20.00 /min.
2. 2

3 RESULTS AND DISCUSSION

Preparation of [Ba3(btc)2(H2O)8]2H2O (1)

A mixture of 1,3,5-benzenetricarboxylate (21.0

3. 1

IR spectrum of 1

mg, 0.1 mmol) and Na2CO3 (2.7 mg, 0.025 mmol)

The infrared spectra of the complex were recorded

was stirred for 10 min in 8 mL water at room

in the range of 4000400 cm-1 with KBr pallets.

temperature. Then BaCl2 (24.4 mg, 0.1 mmol) and 2

The absence of peaks at 1700 cm-1 suggests that

mL DMF were added into this mixture. Finally,

the carboxyl groups are all deprotonated, which

1,10-phenanthroline (10.0 mg, 0.05 mmol) was

agrees with the results of X-ray analysis. The

added into this clear solution. This suspended

absorption peaks at 1625, 1550, 1430 and 1368 cm-1

mixture was sealed in a 25 mL Teflon-lined reactor.

are observed, indicating that the carboxylate groups

The reactor was heated in an oven to 160 for 72 h,

have coordinated with the Ba(II) cations. The peaks

and then cooled to room temperature. The clear

at 1625 and 1550 cm-1 should be ascribed to the

solution was stood still in air for about two weeks.

asymmetrical stretching vibration and those at 1430

Colorless block-shaped crystals of 1 were obtained

and 1368 cm-1 to symmetrical stretching vibration of

by filtration, and dried in air. Anal. Calcd. for

-COO- groups[21]. The separation of as and s (

C18H26Ba3O22 (%): C, 21.48; H, 2.60. Found (%): C,

are 195, 183 and 120 cm-1) implies the coordination

21.44; H, 2.63. FT-IR (KBr pellet, cm-1): 3389(bs),

of carboxyl group with Ba(II) in bridging mo-

2790(m), 1625(s), 1550(s), 1430(m), 1368(s),

des[22-25], which is in agreement with the single-

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crystal X-ray diffraction study.

Table 1.

Selected Bond Lengths () and Bond Angles () for Complex 1

Bond

Dist.

Bond

Dist.

Bond

Ba(1)O(1)

2.728(3)

Ba(1)O(2)

2.857(4)

Ba(1)O(3)

Dist.
2.769(3)

Ba(1)O(4)

2.664(3)

Ba(1)O(5)

2.782(3)

Ba(1)O(8)

2.823(4)

Ba(1)O(9)

2.856(3)

Ba(1)O(11)

2.873(3)

Ba(2)O(5)

2.990(3)

Ba(2)O(5)#1

2.990(3)

Ba(2)O(6)

2.760(3)

Ba(2)O(6)#1

2.760(3)

Ba(2)O(7)

2.817(3)

Ba(2)O(7)#1

2.817(3)

Ba(2)O(8)

3.013(4)

Ba(2)O(8)#1

3.013(4)

Ba(2)O(9)

2.977(3)

Ba(2)O(9)#1

2.977(3)

Angle

()

Angle

()

Angle

()

O(4)Ba(1)O(1)

78.58(10)

O(4)Ba(1)O(3)

148.70(10)

O(1)Ba(1)O(3)

75.65(9)

O(4)Ba(1)O(5)

125.09(11)

O(1)Ba(1)O(5)

155.89(11)

O(3)Ba(1)O(5)

80.44(10)

O(3)Ba(1)O(8)

70.05(10)

O(4)Ba(1)O(8)

134.41(10)

O(1)Ba(1)O(8)

104.19(10)

O(5)Ba(1)O(8)

63.91(10)

O(4)Ba(1)O(9)

75.40(10)

O(1)Ba(1)O(9)

131.26(10)

O(8)Ba(1)O(9)

69.16(10)

O3Ba(1)O(9)

135.63(10)

O(5)Ba(1)O(9)

66.52(10)

O(1)Ba(1)O(2)

93.68(10)

O(5)Ba(1)O(2)

86.35(10)

O(8)Ba(1)O(2)

142.03(11)

O(4)Ba(1)O(2)

81.47(12)

O(9)Ba(1)O(2)

121.73(11)

O(4)Ba(1)O(11)

69.46(10)
114.86(9)

O(3)Ba(1)O(2)

82.75(11)

O(1)Ba(1)O(11)

66.82(10)

O(3)Ba(1)O(11)

O(5)Ba(1)O(11)

122.32(10)

O(8)Ba(1)O(11)

70.30(10)

O(6)Ba(2)O(7)#1

83.02(10)

O(9)Ba(1)O(11)

65.67(9)

O(2)Ba(1)O(11)

147.34(11)

O(6)#1Ba(2)O(9)#1

106.95(9)

O(6)Ba(2)O(6)#1

180.0

O(6)Ba(2)O(7)#1

83.02(10)

O(7)Ba(2)O(9)#1

61.73(9)

O(6)Ba(2)O(7)

96.98(10)

O(6)#1Ba(2)O(7)#1

96.98(10)

O(6)Ba(2)O(9)#1

73.05(9)

O(7)Ba(2)O(7)#1

180.0

O(7)Ba(2)O(9)

118.27(9)

O(7)#1Ba(2)O(9)

61.73(9)

O(6)Ba(2)O(9)#1

73.05(9)

O(9)Ba(2)O(9)#1

180.0

O(6)#1Ba(2)O(5)#1

45.22(9)

O(7)#1Ba(2)O(9)#1

118.27(9)

O(6)Ba(2)O(5)#1

134.78(9)

O(7)Ba(2)O(5)#1

69.46(10)

O(6)Ba(2)O(9)

106.95(9)

O(7)#1Ba(2)O(5)#1

110.54(10)

O(9)#1Ba(2)O(5)#1

62.44(9)

O(9)Ba(2)O(5)#1

117.56(9)

O(6)Ba(2)O(5)#1

134.78(9)

O(6)#1Ba(2)O(8)#1

84.18(10)

O(6)Ba(2)O(5)

45.22(9)

O(7)Ba(2)O(5)

110.54(10)

O(7)#1Ba(2)O(8)

118.12(10)

O(7)Ba(2)O(5)#1

69.46(10)

O(9)Ba(2)O(5)#1

117.56(9)

O(9)#1Ba(2)O(8)#1

65.10(10)

O(9)Ba(2)O(5)

62.44(9)

O(5)Ba(2)O(5)#1

180.0

O(5)#1Ba(2)O(8)#1

59.23(9)

O(6)#1Ba(2)O(8)

95.82(10)

O(6)Ba(2)O(8)#1

95.82(10)

O(6)Ba(2)O(8)

84.18(10)

O(7)#1Ba(2)O(8)#1

61.88(9)

O(7)Ba(2)O(8)

61.88(9)

O(7)Ba(2)O(8)#1

118.12(10)

O(9)Ba(2)O(8)#1

114.90(10)

O(9)Ba(2)O(8)#1

114.90(10)

O(9)Ba(2)O(8)

65.10(10)

O(5)#1Ba(2)O(8)

120.77(9)

O(5)Ba(2)O(8)#1

120.77(9)

O(5)Ba(2)O(8)

59.23(9)

O(8)Ba(2)O(8)#1

180.00(12)

O(8)Ba(2)O(8)#1

180.00(12)

Symmetry transformation: #1: 1 x, 1 y, z

3. 2

Crystal structure of 1

from 2.728(3) to 2.873(3) . The Ba(1)Ow (water,

Complex 1 crystallizes in the monoclinic space

Ba(1)O(2), Ba(1)O(11)) distances are 2.857(4)

group P21/c and possesses a 3D coordination

and 2.873(3) , respectively. The OBa(1)O bond

framework. The ORTEP view of coordination

angles range from 63.91(10) to 155.89(11)o (Table 1).

environment of the Ba(II) atom for compound 1 is

Each Ba(2) ion is ten-coordinated by O atoms

shown in Fig. 1. In complex 1, there are two kinds of

from four btc3- ligands and four 2-bridging coor-

crystallographically independent Ba(II) centers. It is

dination water molecules in a distorted dicapped

seen that the Ba(1) center is coordinated by eight O

square prism (Fig. 1). The Ba(2)O(carboxylate)

3-

anions and three water

bond lengths vary from 2.760(3) to 3.013(4) , and

molecules, two taking monodentate terminal coor-

the Ba(2)Ow(water, Ba(2)O(8), Ba(2)O(9))

dination model and another two adopting 2-brid-

distances are 2.977(3) and 3.013(4) , respectively.

ging coordination model (Fig. 1). The Ba(1) center

The average distance of Ba(2)O is longer than that

is located in a distorted square antiprismatic coor-

of Ba(1)O. The OBa(2)O bond angles range

dination geometry with Ba(1)O distances ranging

from 45.22(9) to 180.00(12)o (Table 1). The distan-

atoms from four btc

1394

WU G. et al.: Synthesis, Crystal Structure and Properties of Barium

Coordination Compound Based on 1,3,5-Benzenetricarboxylic Acid Ligand

No. 9

[26-28]

ces of BaO are in the normal ranges of those observed in the reported Ba(II) compound

Fig. 1. ORTEP view of coordination environment of Ba(II) atom in 1 with 50%

probability displacement. The hydrogen atoms are omitted for clarity

There is only one crystallographically unique

mode. The third carboxylate group takes a 2-2:1

anion of btc3- in the structure. In complex 1, three

coordination mode. Therefore, the whole btc3- anion

carboxylate groups of the anion btc3- take two

acts as a 6-bridge connecting six different Ba(II)

different coordination modes (Scheme 1). Two

ions (Scheme 1).

carboxylate groups take a 2- : bidentate bridging

Scheme 1.

Coordination model of btc3-

In complex 1, the three carboxylate groups are not

mode are 2.1 and 2.6, respectively, which are very

in the same plane with the central benzene ring

close to each other. The dihedral angles between

owing to the rotation of carboxylate groups. The

central ring and the carboxylate group adopting

dihedral angles between central ring and the

2-2:1 tridentate bridging mode is 9.8, suggesting

carboxylate groups taking 2-1:1 bidentate bridging

that there may be relation between the configuration

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1

and coordination model of the ligand.

1395

groups taking 2- : bidentate bridging mode (Fig. 3).

The one-dimensional chains are formed through

1

J.

The 2D networks are further linked together by the

carboxylate groups, taking 2- : bidentate brid-

2-2:1 tridentate bridging carboxylate groups to

ging mode, 2-2:1 coordination mode, and 2-H2O

produce a new 3D porous coordination framework

3-

(Fig. 2). Then the bridged btc ligands link these 1D

(Fig. 4).

chains to generate a 2D network through carboxylate

Fig. 2.

One-dimensional structure in 1

Fig. 3.

Two-dimensional structure in 1

Fig. 4.

Crystal packing diagram of 1

WU G. et al.: Synthesis, Crystal Structure and Properties of Barium

Coordination Compound Based on 1,3,5-Benzenetricarboxylic Acid Ligand

1396

The lattice water molecules locate in the voids

face-to-face

interaction

No. 9

between

adjacent

and are connected to the 3D framework through

benzene rings because the distance of two centroids

OHO hydrogen bonds (Table 2, Fig. 4), formed

is 3.517 with a dihedral angle of 0o, which are

between lattice water and coordinated water

within the normal distances required for -

molecules, with the OO distances in the range

interactions.

from 2.792(5) to 2.981(5) . In complex 1, there is

Table 2.

Distances () and Angles () of Hydrogen Bonds for the Complex

DHA

d(DH) ()

D(HA) ()

d(DA) ()

Angle DHA ()

O(2)H(2B)O(4)#1

0.85

2.37

2.981(5)

129

O(8)H(8A)O(12)#2

0.85

2.04

2.833(5)

156

O(8)H(8B)O(7)#2

0.85

2.20

2.995(5)

156

O(9)H(9A)O(3)#3

0.85

2.05

2.858(5)

159

O(9)H(9B)O(11)#4

0.85

2.17

2.839(5)

135

O(11)H(11A)O(1)#4

0.85

2.23

2.808(5)

125

O(11)H(11B)O(9)#5

0.85

2.16

2.839(5)

137

O(12)H(12A)O(11)#6

0.85

2.12

2.792(5)

135

O(12)H(12B)O(6)#7

0.85

2.02

2.792(5)

150

Symmetry transformation: #1: x, 1 y, z; #2: 1 x, 1 y, 1 z; #3: x, y, 1 + z; #4: x, 1/2 y, 1/2 + z; #5: x,

1/2 y, 1/2 + z; #6: 1 x, 1/2 + y, 1/2 z; #7: x, 3/2 y, 1/2 + z

3. 3

thermal gravimetric (TG) analyses were carried out

Luminescent property of complex 1

The photoluminescent property of complex 1 and

(Fig. 6) under 100.0 mL/min flowing nitrogen,

H3btc ligand were studied in the solid state at room

ramping the temperature at a rate of 20.00 /min

temperature. No clear luminescence was detected for

from room temperature to 600 . The first-step

the H3btc ligand under experimental conditions. In

weight loss of 17.12% (calcd. 17.90%) from 30 to

contrast to the H3btc ligand, the Ba(II) (1) com-

395 corresponds to the removal of ten water

plexes show photoluminescence under the same

molecules per formula unit. The second weight loss

conditions (Fig. 5). Complex 1 exhibits photolumi-

between 395 to 595 of ca. 14.74% corresponds to

nescence with an emission maximum at ca. 403 nm

the loss of benzene (calcd. 15.52 %), as shown in

upon excitation at 320 nm. The luminescence of the

Fig. 6. The solid residue formed at ca. 595 is

complex may be ascribed to transition of organic

suggested to be BaCO3, which was confirmed by

ligand

[28, 29]

powder X-ray diffraction (Fig. 7), with some further

3. 4

Thermogravimetric analyses

evaporation occurring at higher temperature.

To examine the thermal stability of this compound,

100

Weight / %

90

80

70

60

350
Fig. 5.

400
450
Wavelength / nm

500

Luminescence property of complex 1

550

100

200

Fig. 6.

300
400
Temperature / oC

TG curve of 1

500

600

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400
350

Intensity / a.u.

300
250
200
150
100
50
0

Fig. 7.

20

30

40

2/o

50

60

70

PXRD pattern of BaCO3 decomposed from complex 1

CONCLUSION

dicapped square prism. In complex 1, three carboxyl

groups of the anion btc3- take 2-1:1 and 2-2:1

An alkaline earth complex [Ba3(btc)2(H2O)8]2H2O

two different coordination modes. The whole btc3-

(1) has been synthesized and characterized. The

anion acts as a 6-bridge connecting six different

Ba(1) center is located in a distorted square antipri-

Ba(II) ions to result in a three-dimensional network.

smatic coordination geometry, while the coordina-

We also investigated the thermal stability and

tion geometry of Ba(2) is distorted ten-coordinated

luminescent properties of complex 1.

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