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

doi:10.6023/A21110508

Acta Chimica Sinica ›› 2022, Vol. 80 ›› Issue (1): 29-36.DOI: 10.6023/A21110508 Previous Articles Next Articles

Special Issue: 中国科学院青年创新促进会合辑

Article

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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Abstract

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

Cite this article

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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Fig. & Tab. 9

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

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

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)

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

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

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

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

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

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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Supporting Info.

Knowledge

Abstract

Cite this article

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Fig. & Tab. 9

References 32

Related Articles 15

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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^※