Synthesis, Characterization and Photophysical Properties of BN-[4]helicenes

doi:10.6023/cjoc202005005

Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (9): 2879-2887.DOI: 10.6023/cjoc202005005 Previous Articles Next Articles

硼氮[4]螺烯的合成、表征及光物理性质研究

刘秉康^a, 张艳丽^a, 陈瑜^a, 刘旭光^a,c, 张磊^b

a 天津理工大学化学化工学院天津市有机太阳能电池和光化学转换重点实验室&天津市药物靶向与生物成像重点实验室天津 300384;
b 天津城建大学理学院天津 300384;
c 中国科学院上海有机化学研究所有机功能分子合成与组装化学重点实验室上海 200032

收稿日期:2020-05-03 修回日期:2020-06-05 发布日期:2020-06-20
通讯作者: 刘旭光, 张磊 E-mail:xuguangliu@tjut.edu.cn;zhanglei-chem@tcu.edu.cn
基金资助:
国家自然科学基金（No.21502140）、天津市自然科学基金（No.17JCZDJC37700）和有机功能分子合成与组装化学重点实验室开放课题（No.K2015-10）资助项目.

Synthesis, Characterization and Photophysical Properties of BN-[4]helicenes

Liu Bingkang^a, Zhang Yanli^a, Chen Yu^a, Liu Xuguang^a,c, Zhang Lei^b

a Tianjin Key Laboratory of Organic Solar Cells and Photochemical Conversion & Tianjin Key Laboratory of Drug Targeting and Bioimaging, School of Chemistry and Chemical Engineering, Tianjin University of Technology, Tianjin 300384;
b School of Science, Tianjin Chengjian University, Tianjin 300384;
c Key Laboratory of Synthetic and Self-Assembly Chemistry for Organic Functional Molecules, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032

Received:2020-05-03 Revised:2020-06-05 Published:2020-06-20
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21502140), the Natural Science Foundation of Tianjin City (No. 17JCZDJC37700), and the Key Laboratory of Synthetic and Self-Assembly Chemistry for Organic Functional Molecules (No. K2015-10).

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Abstract

Repalcement of C=C bond with an isoeletronic and isosturctural B—N bond is an effective way to tune the photophyscial properties of polycylic aromatic hydrocarbons (PAHs), which have become the hot topic in the filed of optoelectronics. There are relatively smalll number of the non-planar BN-PAHs exsited, compared to the large number of planar BN-PAHs being synthesized. In this paper, the synthesis and properties of two series of non-planar BN[4]helicenes are discribed. The synthesis is quite straightforward by sequence of Suzuki cross coupling reaction, electrophilic borylation and nuleophilic substitution reactions. All of the target BN-[4]helicenes were characterized by ¹H NMR, ¹³C NMR and ¹¹B NMR. One of the BN-[4]helicene was also unmbigiously confired by X-ray crystal analysis, which showed the typical helically twisted geometries. Futhermore, the BC4N ring in the BN[4]helicene exhibited weak aromaticites, wihch were quantitified by experimental and theorectical calculations. Furthermore, both of the two series of BN[4]helicene showed significant redshift of their absorption spectra and slightly blueshift emission spectra comparing to the all-carbon [4]helicene analogue. Also, good fluorescence quantum yields range from 0.42 to 0.70 were obtained for the two series of BN[4]helicenes.

Key words: arenes/aromatics, boron/nitrogen heterocycle, helicene, boron

Cite this article

Liu Bingkang, Zhang Yanli, Chen Yu, Liu Xuguang, Zhang Lei. Synthesis, Characterization and Photophysical Properties of BN-[4]helicenes[J]. Chinese Journal of Organic Chemistry, 2020, 40(9): 2879-2887.

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硼氮[4]螺烯的合成、表征及光物理性质研究

Synthesis, Characterization and Photophysical Properties of BN-[4]helicenes

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