1,3-二叔丁基薁类衍生物的设计合成及性质研究

doi:10.6023/cjoc202407022

有机化学 ›› 2025, Vol. 45 ›› Issue (4): 1297-1305.DOI: 10.6023/cjoc202407022 上一篇下一篇

研究论文

1,3-二叔丁基薁类衍生物的设计合成及性质研究

谢玉龙^a^,^b, 向焌钧^b, 宋贤江^c^,^*(), 张含悦^d^,^*(), 高希珂^b^,^*()

a 中国科学技术大学化学系合肥 230026
b 中国科学院上海有机化学研究所金属有机化学国家重点实验室上海 200032
c 南昌大学国际有序物质科学研究中心南昌 330031
d 东南大学生物科学与医学工程学院数字医学工程全国重点实验室江苏省生物材料与器件重点实验室南京 211189

收稿日期:2024-07-09 修回日期:2024-09-27 发布日期:2024-10-29
基金资助:
国家自然科学基金(22225506); 中国科学院战略性先导科技专项(XDB0610000)

Design, Synthesis, and Properties of 1,3-Di-tert-butylazulene Derivatives

Yulong Xie^a^,^b, Junjun Xiang^b, Xianjiang Song^c(), Hanyue Zhang^d(), Xike Gao^b()

a Department of Chemistry, University of Science and Technology of China, Hefei 230026
b State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032
c Ordered Matter Science Research Center, Nanchang University, Nanchang 330031
d Jiangsu Key Laboratory of Biomaterials and Devices, National Key Laboratory of Digital Medical Engineering, School of Biological Science and Medical Engineering, Southeast University, Nanjing 211189

Received:2024-07-09 Revised:2024-09-27 Published:2024-10-29
Contact: * E-mail: songxj@ncu.edu.cn; zhanghanyue@seu.edu.cn; gaoxk@mail.sioc.ac.cn
Supported by:
National Natural Science Foundation of China(22225506); Strategic Priority Research Program of the Chinese Academy of Sciences(XDB0610000)

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摘要/Abstract

薁是一种为数不多的全碳型偶极分子, 有望通过分子的偶极叠加实现铁电性. 通过理性分析, 设计合成了4个1,3-二叔丁基薁类衍生物, 分别为1,3-二叔丁基薁(1)、1,3-二叔丁基-6-三氟甲基薁(2)、1,3-二叔丁基-6-氟薁(3)和1,3-二叔丁基-5-(6'-薁)基-6-氟薁(4). 这些化合物分别结晶于Aba2、Fdd2、Pna2₁和Cc空间群, 均属于10个极性点群, 且在晶体中均克服了反平行堆积, 具有宏观极化, 其中化合物4以分子偶极一致的方式堆积, 表明大位阻叔丁基团的引入有效降低了分子间偶极-偶极相互作用. 化合物1和4在300 K时具有明显的二次谐波产生(SHG)信号, 约为典型无机铁电体磷酸二氢钾(KDP)的1/4和2/3. 这些研究结果表明, 在薁单元上进行含氟基团取代和5-位修饰都是使薁类衍生物结晶于10个极性点群的有效策略, 为发展新型薁类有机铁电体提供了研究思路.

关键词: 薁, 分子偶极, 铁电性, 叔丁基, 极性点群

Azulene is one of the few all carbon dipole molecules that is expected to achieve ferroelectricity through the superposition of molecular dipoles. Through rational analysis, four 1,3-di-tert-butylazulene derivatives were synthesized, namely 1,3-di-tert-butylazulene (1), 1,3-di-tert-butyl-6-trifluoromethylazulene (2), 1,3-di-tert-butyl-6-fluoroazulene (3), and 1,3-di-tert-butyl-5-(6'-azulene)-6-fluoroazulene (4). The single crystal structures of these compounds are Aba2, Fdd2, Pna2₁, and Cc space groups all belong to 10 polar point groups and overcome antiparallel stacking in the crystal, exhibiting macroscopic polarization. Compound 4 is stacked in a molecular dipole consistent manner. This indicates that the introduction of large steric hindrance tert-butyl groups effectively reduces intermolecular dipole-dipole interactions. Compounds 1 and 4 exhibited significant second harmonic generation (SHG) signals at 300 K, which were approximately 1/4 and 2/3 of the typical inorganic ferroelectric potassium dihydrogen phosphate (KDP). These research results indicate that fluoro-group substitution and 5-site modification on azulene units are effective strategies for obtaining azulene derivatives with 10 polar point groups, providing ideas for the development of new azulene organic ferroelectrics.

Key words: azulene, molecular dipole, ferroelectricity, tert-butyl, polar point group

引用此文

谢玉龙, 向焌钧, 宋贤江, 张含悦, 高希珂. 1,3-二叔丁基薁类衍生物的设计合成及性质研究[J]. 有机化学, 2025, 45(4): 1297-1305.

Yulong Xie, Junjun Xiang, Xianjiang Song, Hanyue Zhang, Xike Gao. Design, Synthesis, and Properties of 1,3-Di-tert-butylazulene Derivatives[J]. Chinese Journal of Organic Chemistry, 2025, 45(4): 1297-1305.

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图/表 12

图式1. 化合物1~4的合成路线

Scheme 1. Synthetic routes of compounds 1~4

图1. 化合物1~4的1H NMR图谱

Figure 1. 1H NMR spectra of compounds 1~4

Compd.	Temperature/K	Crystal system	Point group	Space group
1	213	Orthorhombic	mm2	Aba2
2	213	Orthorhombic	mm2	Fdd2
3	293	Orthorhombic	mm2	Pna2₁
4	173	Monoclinic	m	Cc

表1. 化合物1~4的单晶数据

Table 1. Single crystal data of compounds 1~4

图2. 化合物1的单晶结构图(a)和分子堆积图(b)

Figure 2. Single crystal structure (a) and molecular packing (b) of compound 1

图3. 化合物2的单晶结构图(a)和分子堆积图(b)

Figure 3. Single crystal structure (a) and molecular packing (b) of compound 2

图4. 化合物3的单晶结构图(a)和分子堆积图(b)

Figure 4. Single crystal structure (a) and molecular packing (b) of compound 3

图5. 化合物4的单晶结构图(a)和分子堆积图(b)

Figure 5. Single crystal structure (a) and molecular packing (b) of compound 4

图6. 化合物4的偶极矩理论计算(结构优化和频率计算在B3LYP/6-31G(d,p)理论水平上进行, 偶极矩计算在B3LYP/ aug-cc-PVTZ理论水平上进行)

Figure 6. Theoretical calculation of dipole moment for compound 4 (structural optimization and frequency calculation was performed at the B3LYP/6-31G(d,p) theoretical level, and dipole moment calculation was performed at the B3LYP/aug-cc-PVTZ theoretical level)

Compd.	λ_max^a/nm	ε/(L•mol^－1•cm^－1)	λ_edge/nm	$E_{\text{g}}^{\text{opt}}$^b/eV	E_HOMO^c/eV	E_LUMO^d/eV
1	288	1.18×10⁵	808	1.53	－5.17	－3.64
2	290	9.57×10⁴	867	1.43	－5.38	－3.95
3	292	7.24×10⁴	764	1.62	－5.30	－3.68
4	299	1.22×10⁵	756	1.64	－5.20	－3.56

表2. 化合物1~4的光谱和电化学数据

Table 2. Spectral and electrochemical data of compounds 1~4

图7. 化合物1~4在二氯甲烷溶液中的紫外-可见吸收光谱(浓度均为1.0×10－5mol/L)

Figure 7. UV-Vis absorption spectra of compounds 1~4 in dichloromethane solution (the concentration is 1.0×10－5 mol/L)

图8. 化合物1~4在二氯甲烷溶液中的循环伏安曲线

Figure 8. Cyclic voltammograms of compounds 1~4 in dichloromethane solution With 0.1 mol?L－1 Bu4NPF6 as supporting electrolyte, SCE as reference electrode, scanning rate of 100 mV?s－1. The concentration is 1.0×10－3 mol?L－1

图9. 300 K温度下化合物1~4和KDP的SHG信号强度

Figure 9. SHG signal intensity of compounds 1~4 and KDP at 300 K

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1,3-二叔丁基薁类衍生物的设计合成及性质研究

Design, Synthesis, and Properties of 1,3-Di-tert-butylazulene Derivatives

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