硼氮杂薁基[4]螺烯的设计合成及性质研究※

doi:10.6023/A21110508

化学学报 ›› 2022, Vol. 80 ›› Issue (1): 29-36.DOI: 10.6023/A21110508 上一篇下一篇

所属专题：中国科学院青年创新促进会合辑

研究论文

硼氮杂薁基[4]螺烯的设计合成及性质研究^※

段超^a, 张建伟^b, 向焌钧^a, 杨笑迪^b^,^*(), 高希珂^a^,^*()

^a中国科学院大学中国科学院上海有机化学研究所中国科学院有机功能分子合成与组装化学重点实验室上海 200032
^b上海中医药大学创新中药研究院上海 201203

投稿日期:2021-11-09 发布日期:2021-12-08
通讯作者: 杨笑迪, 高希珂
作者简介:
^※ 庆祝中国科学院青年创新促进会十年华诞.
基金资助:
项目受国家自然科学基金(21790362); 项目受国家自然科学基金(22075310); 上海市科学技术委员会项目(19XD1424700); 上海市科学技术委员会项目(18JC1410600)

Design, Synthesis and Properties of Azulene-Based BN-[4]Helicenes^※

Chao Duan^a, Jianwei Zhang^b, Junjun Xiang^a, Xiaodi Yang^b(), Xike Gao^a()

^aKey Laboratory of Synthetic and Self-Assembly Chemistry for Organic Functional Molecules, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, Shanghai 200032, China
^bInnovation Research Institute of Traditional Chinese Medicine, Shanghai University of Traditional Chinese Medicine, Shanghai 201203, China

Received:2021-11-09 Published:2021-12-08
Contact: Xiaodi Yang, Xike Gao
About author:
^※ Dedicated to the 10th anniversary of the Youth Innovation Promotion Association, CAS.
Supported by:
National Natural Science Foundation of China(21790362); National Natural Science Foundation of China(22075310); Science and Technology Commission of Shanghai Municipality(19XD1424700); Science and Technology Commission of Shanghai Municipality(18JC1410600)

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摘要/Abstract

本工作设计合成了分别含有B—N键和C=C键的薁基[4]螺烯类分子1a/1b和2, 其中B—N键和C=C键互为等电子体. 紫外-可见吸收光谱、电化学循环伏安测试和理论计算结果表明B—N键可以调控共轭骨架的电子结构及芳香性. 单晶结构表明1a具有螺旋几何构型, 晶体中存在P和M两种对映异构体. B—N键具有部分双键性质, 硼氮六元环具有一定的芳香性. 大位阻基团2,4,6-三甲基苯基(Mes)使得1b在三氟乙酸(TFA)作用下不会发生类似于1a的脱硼化, 而是发生和2相似的可逆质子响应, B—N键对薁单元的质子响应性质无明显影响. 三配位的硼原子可以进一步和氟离子配位, 使得1a对氟离子有明显的选择性响应, 而1b则因大位阻的Mes取代基的存在对氟离子无明显的响应性. 本工作报道了新型薁基硼氮杂螺烯及全碳螺烯分子, 为薁基多环芳烃的“自下而上”合成及性质研究提供了参考.

关键词: 薁, 硼氮杂多环芳烃, 螺烯, 质子化

Azulene is a nonalternant and nonbenzenoid hydrocarbon with bright blue color and a dipole moment of 1.08 D, and has received increasing attention due to its unique electronic structure and physicochemical properties. Herein, we report the design and synthesis of two types of azulene-based [4]helicene 1a/1b and 2 that contain isoelectronic B—N and C=C units at the electron-rich 1-position of azulene unit, respectively. Formation of the helical scaffolds is executed by the introduction of boron and alkyne to flexible biaryl precursors, where the Lewis acidic boron and alkyne were employed as “glue” to join two subunits into fully fused scaffolds via electrophilic boronation and platinum-catalyzed cycloisomerization of alkyne at the 1-position of azulene unit, respectively. All of azulene-based helicenes were investigated by ultraviolet visible (UV-vis) absorption spectra, cyclic voltammetry (CV) measurements and density functional theory (DFT) calculations. Additionally, 1a was further characterized by single crystal structure analysis. The results suggest that the introduction of B—N unit changed the electronic structure of the conjugated aromatic framework, leading to a narrow HOMO-LUMO gap. Moreover, the B—N unit also affects the aromaticity of the π-system as revealed by nucleus-independent chemical shift (NICS) via time-dependent density functional theory (TD-DFT) calculation. The single crystal structure analysis demonstrates that 1a has a helically twisted framework and Plus (P)/Minus (M) enantiomers. However, the Gibbs activation energy (ΔG^≠(T)) of the enantiomerization at room temperature is too low to separate two enantiomers by chiral high performance liquid chromatography (HPLC). Furthermore, the B—N unit exhibits partial double bond character and the BN-containing six-membered ring shows weak aromaticity. 1a with a phenyl group exhibits the deboronization upon addition of trifluoroacetic acid (TFA) as well as a specific sensing behavior to fluoride ion. However, 1b shows no deboronization upon addition of TFA and no sensing behavior to fluoride ion due to its steric hindered mesityl (Mes) group, but has a reversible stimuli-responsiveness with acid and base, this proton-responsiveness is similar to all-carbon analogue 2.

Key words: azulene, BN-heteroaromatic, helicene, protonation

引用此文

段超, 张建伟, 向焌钧, 杨笑迪, 高希珂. 硼氮杂薁基[4]螺烯的设计合成及性质研究^※[J]. 化学学报, 2022, 80(1): 29-36.

Chao Duan, Jianwei Zhang, Junjun Xiang, Xiaodi Yang, Xike Gao. Design, Synthesis and Properties of Azulene-Based BN-[4]Helicenes^※[J]. Acta Chimica Sinica, 2022, 80(1): 29-36.

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图/表 9

图式1. 薁基螺烯1a/1b和2的合成路线

Scheme 1. Synthesis routes of azulene-embedded helicenes 1a/1b and 2

图1. 化合物S4, 1a/1b及2的部分1H NMR谱图

Figure 1. Partial 1H NMR spectra of compounds S4, 1a/1b and 2

图2. 1a 的单晶结构(已略去氢原子): (a) 俯视图, (b) 侧视图, (c) 堆积图(红色: M对映异构体; 蓝色: P对映异构体)

Figure 2. Crystal structure of 1a (hydrogen atoms are omitted): (a) top view, (b) side view, and (c) packing diagrams (red: M enantiomer; blue: P enantiomer)

图3. DFT计算获得的1a和2的前线轨道及轨道能级

Figure 3. Frontier molecular orbitals and energy levels of 1a and 2 obtained by DFT calculations

图4. 1a和2的NICS (1)值

Figure 4. NICS (1) values of 1a and 2

图5. (a) 1a/1b和2在二氯甲烷溶液中的紫外-可见吸收光谱(1×10-5 mol/L); (b) 1a/1b和2在二氯甲烷(0.1 mol/L Bu4NPF6作为支持电解质, 甘汞电极作为参比, 扫描速率100 mV/s)中的循环伏安曲线 (a) 1a/1b和2在二氯甲烷溶液中的紫外-可见吸收光谱(1×10-5 mol/L); (b) 1a/1b和2在二氯甲烷(0.1 mol/L Bu4NPF6作为支持电解质, 甘汞电极作为参比, 扫描速率100 mV/s)中的循环伏安曲线

Figure 5. (a) UV-Vis absorption spectra of 1a/1b and 2 in dichloromethane solutions (1×10-5 mol/L); (b) cyclic voltammograms of 1a/1b and 2a in dichloromethane (0.1 mol/L Bu4NPF6 as supporting electrolyte, SCE as reference electrode, scan rate of 100 mV/s) (a) UV-Vis absorption spectra of 1a/1b and 2 in dichloromethane solutions (1×10-5 mol/L); (b) cyclic voltammograms of 1a/1b and 2a in dichloromethane (0.1 mol/L Bu4NPF6 as supporting electrolyte, SCE as reference electrode, scan rate of 100 mV/s)

Compound	λ_max/nm	E_g^opt^a/V	E_HOMO^b/eV	E_LUMO^b/eV	E_HOMO ^c/eV	E_LUMO ^c/eV	E_g^c/V
1a	305, 332	2.66	–5.21	–2.91	–5.36	–2.30	3.06
1b	305, 332	2.67	–5.26	–2.87	—	—	—
2	350	2.72	–4.96	–2.95	–5.13	–2.36	2.77

表1. 1a/1b和2的光谱、电化学和理论计算数据

Table 1. Optical, electrochemical and DFT calculations data for 1a/1b and 2

图6. (a) 1b在二氯甲烷溶液中质子化和去质子化过程的紫外-可见吸收光谱及颜色变化; (b) 2在二氯甲烷溶液中质子化和去质子化过程的紫外-可见吸收光谱及颜色变化

Figure 6. (a) UV-Vis absorption spectra and colour change of 1b during protonation and deprotonation in dichloromethane solutions; (b) UV-Vis absorption spectra and colour change of 2 during protonation and deprotonation in dichloromethane solutions

图7. (a) 1a的二氯甲烷溶液中加入不同阴离子的四丁基铵盐TBAX (nTBAX/n1a=10)后的紫外-可见吸收光谱及颜色变化; (b) 1b的二氯甲烷溶液中加入不同阴离子的四丁基铵盐TBAX (nTBAX/n1b=10)后的紫外-可见吸收光谱及颜色变化

Figure 7. (a) UV-Vis absorption spectra and colour change of 1a after addition of tetrabutylammonium salts TBAX of different anions (nTBAX/n1a=10) in dichloromethane solutions; (b) UV-Vis absorption spectra and colour change of 1b after addition of tetrabutylammonium salts TBAX of different anions (nTBAX/n1b=10) in dichloromethane solutions

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硼氮杂薁基[4]螺烯的设计合成及性质研究^※

Design, Synthesis and Properties of Azulene-Based BN-[4]Helicenes^※

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硼氮杂薁基[4]螺烯的设计合成及性质研究※

Design, Synthesis and Properties of Azulene-Based BN-[4]Helicenes※

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硼氮杂薁基[4]螺烯的设计合成及性质研究^※

Design, Synthesis and Properties of Azulene-Based BN-[4]Helicenes^※