卤代芳香族羧酸与含氮配体合成镧系配合物的结构、热化学和荧光性质

doi:10.3866/PKU.WHXB202206035

物理化学学报 >> 2023, Vol. 39 >> Issue (1): 2206035.doi: 10.3866/PKU.WHXB202206035

卤代芳香族羧酸与含氮配体合成镧系配合物的结构、热化学和荧光性质

王晨璐¹, 宿素玲², 任宁³^,*(), 张建军¹^,*()

¹ 河北师范大学分析测试中心, 化学与材料科学学院, 石家庄 050024
² 河北省特种设备监督检验研究院, 石家庄 050000
³ 邯郸学院, 化学化工与材料学院, 河北省杂环化合物重点实验室, 河北邯郸 056005

收稿日期:2022-06-24 录用日期:2022-07-12 发布日期:2022-07-20
通讯作者: 任宁,张建军 E-mail:ningren9@163.com;jjzhang6@126.com
基金资助:
国家自然科学基金(22273015);国家自然科学基金(21803016)

Construction, Thermochemistry, and Fluorescence Properties of Novel Lanthanide Complexes Synthesized from Halogenated Aromatic Carboxylic Acids and Nitrogen-Containing Ligands

Chenlu Wang¹, Suling Xu², Ning Ren³^,*(), Jianjun Zhang¹^,*()

¹ Testing and Analysis Center, College of Chemistry & Material Science, Hebei Normal University, Shijiazhuang 050024, China
² Hebei Special Equipment Supervision and Inspection Institute, Shijiazhuang 050000, China
³ College of Chemical Engineering & Material, Hebei Key Laboratory of Heterocyclic Compounds, Handan University, Handan 056005, Hebei Province, China

Received:2022-06-24 Accepted:2022-07-12 Published:2022-07-20
Contact: Ning Ren,Jianjun Zhang E-mail:ningren9@163.com;jjzhang6@126.com
About author:Email: ningren9@163.com; +86-310-6260302 (R.N.)
Email: jjzhang6@126.com; Tel.: +86-311-80786457 (Z.J.)
Supported by:
the National Natural Science Foundation of China(22273015);the National Natural Science Foundation of China(21803016)

摘要/Abstract

摘要：

采用室温溶液挥发法合成了五种结构新颖的镧系配合物，其结构通式为[Ln(2, 4-DFBA)₃(phen)]₂ (Ln = Sm 1, Eu 2, Er 3, 2, 4-DFBA为2, 4二氟苯甲酸的简写，phen为1, 10-菲啰啉的简写), [Ln(2-Cl-6-FBA)₂(terpy)(NO₃)(H₂O)]₂ (Ln = Tb 4, Dy 5, 2-Cl-6-FBA为2-氯-6-氟苯甲酸的简写, terpy为2, 2’: 6’2’’-三联吡啶的简写)。五个配合物可以分为两个系列，使用不同的镧系离子作为中心离子。通过X射线单晶分析，5种配合物均属于单斜晶系，空间群为P2₁/n。配合物1，2和配合物3虽然具有相同的分子通式，但配位方式明显不同，形成了前者为9配位的松饼型，后者是8配位的双帽三棱柱几何构型。二维面状超分子结构的形成方式也明显不同，区别在于配合物1和2通过微弱的π-π堆积作用形成。配合物4和5是同构的，结构中引入了硝酸根离子较为有趣，通过C―H∙∙∙F氢键和π-π堆积作用形成二维面状超分子结构。在299.25–1073.15 K温度下对配合物1–5通过热重-微分热重-差示扫描量热/红外光谱(TG-DTG-DSC/FTIR)联用技术进行热分解机理的研究。测定了配合物1, 2, 4, 5的固体荧光，特征过渡峰位于⁴G_5/2 → ⁶H_5/2, ⁴G_5/2 → ⁶H_7/2, ⁴G_5/2 → ⁶H_9/2 (1), ⁵D₀ → ⁷F₀, ⁵D₀ → ⁷F₁, ⁵D₀ → ⁷F₂, ⁵D₀ → ⁷F₃, ⁵D₀ → ⁷F₄ (2), ⁵D₄ → ⁷F₆, ⁵D₄ → ⁷F₅, ⁵D₄ → ⁷F₄, ⁵D₄ → ⁷F₃ (4), 和⁴F_9/2 → ⁶H_15/2, ⁴F_9/2 → ⁶H_13/2 (5)，均表现出镧系离子的特征过渡峰。此外，还对配合物2和4进行了荧光寿命的研究，其荧光衰减时间分别为1.288和0.648 ms。

关键词: 镧系配合物, 超分子结构, 热化学, 三维红外, 荧光性质

Abstract:

In this study, new lanthanide complexes were synthesized via the volatilization method in solution at room temperature. The general molecular formulas for the lanthanide complexes are as follows: [Ln(2, 4-DFBA)₃(phen)]₂ (Ln = Sm 1, Eu 2, and Er 3; 2, 4-DFBA = 2, 4-difluorobenzoate; and phen = 1, 10-phenanthroline), as well as [Ln(2-Cl-6-FBA)₂(terpy)(NO₃)(H₂O)]₂ (Ln = Tb 4 and Dy 5; 2-Cl-6-FBA = 2-chloro-6-fluorobenzoate; and terpy = 2, 2': 6'2''-tripyridine). Based on single-crystal X-ray analysis, the five complexes exhibited a monoclinic crystal structure belonging to the space group P2₁/n. Even though complexes 1, 2 (I), and 3 (II) share a general molecular formula, their coordination modes were different. For example, complexes 1 and 2 formed a muffin-like structure with nine coordinated atoms, while complex 3 formed a double hat triangular geometry with eight coordinated atoms. The two-dimensional (2D) polyhedral structures of complexes 1 and 2 were formed via weak π-π stacking interactions, whereas complex 3 exhibited a 2D faceted supramolecular structure through C―H∙∙∙F hydrogen bonds. Complexes 4 and 5 were isostructural, with the presence of nitrate ions in their structure. This occurred through the C―H∙∙∙F hydrogen bonds and π-π stacking of the molecules to form a faceted supramolecular crystal structure. A series of characterizations, such as elemental analysis, infrared and Raman spectroscopy, as well as powder X-ray diffraction, were performed on the five complexes. Thermogravimetry-derivative thermogravimetry-differential scanning calorimetry were performed between 299.25 and 1073.15 K to investigate the mechanism for the thermal decomposition of complexes 1–5. The analysis of the escaping gas stacking maps of the five complexes using thermogravimetric and 3D infrared coupling techniques further confirmed the correctness of the thermal decomposition mechanism of each complex. The results obtained revealed that similar structured complexes follow a similar thermal decomposition mechanism, and the end solid products for all complexes were their corresponding metal oxides. During the irradiation of the Xe lamp, the solid fluorescence of complexes 1, 2, 4, and 5 were measured. The characteristic transition peaks were located at ⁴G_5/2 → ⁶H_5/2, ⁴G_5/2 → ⁶H_7/2, and ⁴G_5/2 → ⁶H_9/2 (1); ⁵D₀ → ⁷F₀, ⁵D₀ → ⁷F₁, ⁵D₀ → ⁷F₂, ⁵D₀ → ⁷F₃, and ⁵D₀ → ⁷F₄ (2); ⁵D₄ → ⁷F₆, ⁵D₄ → ⁷F₅, ⁵D₄ → ⁷F₄, and ⁵D₄ →⁷F₃ (4); and ⁴F_9/2 → ⁶H_15/2, ⁴F_9/2 → ⁶H_13/2 (5). The peaks observed indicated the characteristic transitions of Ln(III). The lanthanide complexes exhibited characteristic fluorescence due to this fact, which also explained their characteristic color. Furthermore, the fluorescence lifetimes of complexes 2 and 4 were measured, and their fluorescence decay curves indicated fluorescence lifetimes of 1.288 and 0.648 ms, respectively.

Key words: Lanthanide complexes, Supramolecular structure, Thermochemistry, Three-dimensional infrared, Fluorescent properties

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王晨璐, 宿素玲, 任宁, 张建军. 卤代芳香族羧酸与含氮配体合成镧系配合物的结构、热化学和荧光性质[J]. 物理化学学报, 2023, 39(1): 2206035.

Chenlu Wang, Suling Xu, Ning Ren, Jianjun Zhang. Construction, Thermochemistry, and Fluorescence Properties of Novel Lanthanide Complexes Synthesized from Halogenated Aromatic Carboxylic Acids and Nitrogen-Containing Ligands[J]. Acta Phys. -Chim. Sin., 2023, 39(1): 2206035.

图/表 13

Table 1

Structural refinement parameters of complexes 1–5."

Complex	1	2	3	4	5
empirical formula	C₆₆H₃₄F₁₂Sm₂N₄O₁₂	C₆₆H₃₄F₁₂Eu₂N₄O₁₂	C₆₆H₃₄F₁₂Er₂N₄O₁₂	C₅₈H₃₈Cl₄F₄Tb₂N₈O₁₆	C₅₈H₃₈Cl₄F₄Dy₂N₈O₁₆
formula weight/(g?mol^?1)	1603.67	1606.89	1637.49	1638.60	1645.76
temperature/K	293(2)	293(2)	293(2)	293(2)	293(2)
wavelength/Å	0.71073	0.71073	0.71073	0.71073	0.71073
crystal system	monoclinic	monoclinic	monoclinic	monoclinic	monoclinic
space group	P2₁/n	P2₁/n	P2₁/n	P2₁/n	P2₁/n
a/Å	15.0399(15)	14.9790(14)	14.9639(16)	10.4500(20)	10.4626(11)
b/Å	13.5892(14)	13.5227(13)	13.5102(15)	19.3360(20)	19.4362(18)
c/Å	15.2214(16)	15.1193(15)	15.0220(16)	14.9297(15)	14.9887(12)
α/(°)	90	90	90	90	90
β/(°)	109.562(4)	109.424(3)	109.204(3)	104.040(4)	104.166(3)
γ/(°)	90	90	90	90	90
volume/Å³	2931.4(5)	2888.2(5)	2867.9(5)	2926.6(8)	2955.3(5)
Z, calculated density/(mg?m^?3)	2, 1.817	2, 1.848	2, 1.896	2, 1.859	2, 1.849
absorption coefficient/mm^?1	2.092	2.262	3.017	2.671	2.780
F(000)	1572	1576	1596	1608	1612
crystal size/mm³	0.16 × 0.15 × 0.08	0.29 × 0.21 × 0.10	0.21 × 0.17 × 0.10	0.15 × 0.13 × 0.11	0.27 × 0.10 × 0.08
θ range for data collection/(°)	2.06 to 25.02	2.08 to 25.02	2.08 to 25.01	2.15 to 25.02	2.10 to 25.02
limiting indices	?17 ≤ h ≤ 17	?17 ≤ h ≤ 17	?17 ≤ h ≤ 9	?12 ≤ h ≤ 12	?10 ≤ h ≤ 12
	?14 ≤ k ≤ 16	?16 ≤ k ≤ 15	?16 ≤ k ≤ 15	?22 ≤ k ≤ 23	?21 ≤ k ≤ 23
	?9 ≤ l ≤ 18	?17 ≤ l ≤ 14	?16 ≤ l ≤ 17	?17 ≤ l ≤ 12	?17 ≤ l ≤ 17
reflections collected/unique	12356/5139 [R_(int) = 0.0875]	14100/5081 [R_(int) = 0.0862]	13813/5045 [R_(int) = 0.1245]	14531/5156 [R_(int) = 0.0628]	14072/5172 [R_(int) = 0.0585]
completeness to θ = 25.02°	99.3%	99.9%	99.9%	99.9%	99.3%
max. and min. transmission	0.8505 and 0.7307	0.8054 and 0.5599	0.7523 and 0.5699	0.7577 and 0.6901	0.8082 and 0.5206
data/restraints/parameters	5139/36/437	5081/36/437	5045/0/433	5156/114/416	5172/120/416
goodness-of-fit on F²	1.036	1.044	1.066	1.054	1.042
final R indices [I > 2σ(I)]	R₁ = 0.0610, wR₂ = 0.1160	R₁ = 0.0537, wR₂ = 0.0936	R₁ = 0.0588, wR₂ = 0.1239	R₁ = 0.0417, wR₂ = 0.0911	R₁ = 0.0463, wR₂ = 0.0917
R indices (all data)	R₁ = 0.1082, wR₂ = 0.1289	R₁ = 0.0889, wR₂ = 0.0906	R₁ = 0.0882, wR₂ = 0.1342	R₁ = 0.0622, wR₂ = 0.0980	R₁ = 0.0714, wR₂ = 0.0980
largest diff. peak and hole (e?Å ^?3)	2.251 and ?1.657	1.492 and ?1.471	2.083 and ?1.884	1.112 and ?1.189	1.564 and ?1.987

Table 1

Fig 1

Fig 2

Fig 3

Fig 4

Fig 5

Table 2

Fig 6

Fig 7

Fig 8

Fig 9

Fig 10

Fig 11

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	Step	Temperature/K	DTG T_p/K	Mass loss rate/%		Probably expelled groups	Intermediate and residue
				Found	Calcd.
1	I	444.15–708.15	615.75	57.71	22.47 ^a	2phen + x 2, 4-DFBA	[Sm₂(2, 4-DFBA)_6?x]
	II	708.15–1067.15	766.75	19.89	55.78 ^b	(6 ? x) 2, 4-DFBA	Sm₂O₃
	Sum			77.6	78.25
2	I	466.15–693.15	615.65	57.61	22.43 ^a	2phen + x 2, 4-DFBA	[Eu₂(2, 4-DFBA)_6?x]
	II	693.15–1016.15	735.65	19.29	55.67 ^b	(6 ? x) 2, 4-DFBA	Eu₂O₃
	Sum			76.9	78.1
3	I	437.15–674.15	626.25	55.33	22.01 ^a	2 phen + x 2, 4-DFBA	[Er₂(2, 4-DFBA)_6?x]
	II	674.15–801.15	787.55	12.21		y 2, 4-DFBA	[Er₂(2, 4-DFBA)_6?x?y]
	III	801.15–1022.15	821.95	10.95	54.63 ^b	(6 ? x ? y) 2, 4-DFBA	Er₂O₃
	Sum			78.49	76.64
4	I	424.15–489.15	474.25	2.38	2.20 ^c	2H₂O	[Tb(2-Cl-6-FBA)₂(terpy)(NO₃)]₂
	II	489.15–627.15	601.15	36.34	36.04 ^d	2 terpy + 2NO₃^?	[Tb(2-Cl-6-FBA)₂]₂
	III	627.15–786.15	765.55	24.77		x 2-Cl-6-FBA	Tb₂(2-Cl-6-FBA)_4?x
	IV	786.15–996.15	798.25	12.78	38.95 ^e	(4 ? x) 2-Cl-6-FBA	1/2 Tb₄O₇
	Sum				77.19
5	I	403.15–480.15	423.15	2.23	2.19 ^c	2H₂O	[Dy(2-Cl-6-FBA)₂(terpy)(NO₃)]₂
	II	480.15–723.15	548.75	35.90	35.88 ^d	2 terpy + 2NO₃^?	[Dy(2-Cl-6-FBA)₂]₂
	III	723.15–780.15	766.85	10.54		x 2-Cl-6-FBA	Dy₂(2-Cl-6-FBA)_4-x
	IV	780.15–977.15	808.05	28.64	39.27 ^e	(4 ? x)2-Cl-6-FBA	Dy₂O₃
	Sum				77.34

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卤代芳香族羧酸与含氮配体合成镧系配合物的结构、热化学和荧光性质

Construction, Thermochemistry, and Fluorescence Properties of Novel Lanthanide Complexes Synthesized from Halogenated Aromatic Carboxylic Acids and Nitrogen-Containing Ligands

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