硼氮[4]螺烯的合成、表征及光物理性质研究

doi:10.6023/cjoc202005005

有机化学 ›› 2020, Vol. 40 ›› Issue (9): 2879-2887.DOI: 10.6023/cjoc202005005 上一篇下一篇

研究论文

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).

文章分享

1. cjoc202005005.pdf(1322KB)

摘要/Abstract

将多环芳烃中的碳碳双键替换成等电子体和等结构体的硼氮键是有效调节多环芳烃光物理性质的手段之一，已成为有机材料领域研究的热点.文献中报道的多是平面型的硼氮芳烃分子，非平面的硼氮芳烃研究相对较少.本工作研究了两个系列非平面的硼氮[4]螺烯分子的合成和性质，通过Suzuki偶联、亲电芳香硼化及亲核取代反应，简洁地合成了目标分子，并通过¹H NMR、¹³C NMR和¹¹B NMR等表征.单晶结构表明硼氮[4]螺烯具有螺烯的特征螺旋结构.结合理论计算对硼氮[4]螺烯的芳香性进行了定性定量分析，发现硼氮[4]螺烯的硼氮子环具有弱的芳香性.光物理研究表明，硼氮[4]螺烯相对于全碳螺烯，表现出了显著的红移吸收光谱和轻微的蓝移发射光谱，以及较高的荧光量子产率.

关键词: 芳烃, 硼氮杂环, 螺烯, 硼

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

引用此文

刘秉康, 张艳丽, 陈瑜, 刘旭光, 张磊. 硼氮[4]螺烯的合成、表征及光物理性质研究[J]. 有机化学, 2020, 40(9): 2879-2887.

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.

导出引用 EndNote|Reference Manager|ProCite|BibTeX|RefWorks

分享此文

参考文献

[1] Miao, Q. Polycyclic Arenes and Heteroarenes. Synthesis. Properties. and Applications, Wiley-VCH Verlag GmbH & Co., Weinheim, 2016.
[2] Narita, A.; Wang, X.-Y.; Feng, X.; Müllen, K. Chem. Soc. Rev. 2015, 44, 6616.
[3] Chou, C.-M.; Nobusue, S.; Saito, S.; Inoue, D.; Hashizume, D.; Yamaguchi, S. Chem. Sci. 2015, 6, 2354.
[4] (a) Wang, C.; Dong, H.; Hu, W.; Liu, Y.; Zhu, D. Chem. Rev. 2012, 112, 2208.
(b) Mei, J.; Diao, Y.; Appleton, A. L.; Fang, L.; Bao, Z. J. Am. Chem. Soc. 2013, 135, 6724.
[5] Stępień, M.; Gońka, E.; Żyła, M.; Sprutta, N. Chem. Rev. 2017, 117, 3479.
[6] (a) Campbell, P. G.; Marwitz, A. J. V.; Liu, S.-Y. Angew.Chem.. Int. Ed. 2012, 51, 6074.
(b) Wang, X.; Wang, J.; Pei, J. Chem. Eur. J. 2015, 21, 3528.
(c) Wang, J. Y.; Pei, J. Chin. Chem. Lett. 2016, 27, 1139.
(d) Wang, J. Y. Univ. Chem. 2017, 32, 1(in Chinese). (王婕妤, 大学化学, 2017, 32, 1.)
[7] (a) Wang, X.; Zhang, F.; Liu, J.; Tang, R.; Fu, Y.; Wu, D.; Xu, Q.; Zhuang, X.; He, G.; Feng, X. Org. Lett. 2013, 15, 5714.
(b) Li, G.; Zhao, Y.; Li, J.; Cao, J.; Zhu, J.; Sun, X. W.; Zhang, Q. J. Org. Chem. 2015, 80, 196.
(c) Zhang, W.; Zhang, F.; Tang, R.; Fu, Y.; Wang, X.; Zhuang, X.; He, G.; Feng, X. Org. Lett. 2016, 18, 3618.
(d) Wang, S.; Yang, D.; Lu, J.; Shimogawa, H.; Gong, S.; Wang, X.; Mellerup, S. K.; Wakamiya, A.; Chang, Y.; Yang, C.; Lu, Z. Angew. Chem.. Int. Ed. 2015, 54, 15074.
(e) Hashimoto, S.; Ikuta, T.; Shiren, K.; Nakatsuka, S.; Ni, J.; Nakamura, M.; Hatakeyama, T. Chem. Mater. 2014, 26, 6265.
(f) Qiang, P.; Sun, Z.; Wan, M.; Wang, X.; Thiruvengadam, P.; Bingi, C.; Wei, W.; Zhu, W.; Wu, D.; Zhang, F. Org. Lett. 2019, 21, 4575.
[8] (a) Wang, X.; Lin, H.; Lei, T.; Yang, D.; Zhuang, F.; Wang, J.; Yuan, S.; Pei, J. Angew. Chem.. Int. Ed. 2013, 52, 3117.
(b) Wang, X.; Zhuang, F.; Wang, R.; Wang, X.; Cao, X.; Wang, J.; Pei, J. J. Am. Chem. Soc. 2014, 136, 3764.
(c) Zhuang, F.-D.; Sun, Z.-H.; Yao, Z.-F.; Chen, Q.-R.; Huang, Z.; Yang, J.-H.; Wang, J.-Y.; Pei, J. Angew. Chem.. Int. Ed. 2019, 58, 1.
[9] Crossley, D. L.; Cade, I. A.; Clark, E. R.; Escande, A.; Humphries, M. J.; King, S. M.; Vitorica-Yrezabal, I.; Ingleson, M. J.; Turner, M. L. Chem. Sci. 2015, 6, 5144.
[10] Huang, H.-N.; Zhou, Y.; Wang, M.; Zhang, J.-Y.; Cao. X.-H.; Wang, S.-T.; Cao, D.-P.; Cui, C.-M. Angew. Chem.. Int. Ed. 2019, 58, 10132.
[11] (a) Liu, Z.; Ishibashi, J. S. A.; Darrigan, C.; Dargelos, A.; Chrostowska, A.; Li, B.; Vasiliu, M.; Dixon, D. A.; Liu, S.-Y. J. Am. Chem. Soc. 2017, 139, 6082.
(b) Zhuang, F. D.; Han, J. M.; Tang, S.; Yang, J. H.; Chen, Q. R.; Wang, J. Y.; Pei, J. Organometallics 2017, 36, 2479.
(c) Liu, X.; Wu, P.; Li, J.; Cui, C. J. Org. Chem. 2015, 80, 3737.
(d) Sun, F.; Lv, L.; Huang, M.; Zhou, Z.; Fang, X. Org. Lett. 2014, 16, 5024.
[12] (a) Zhang, C.; Zhang, L.; Sun, C.; Sun W.; Liu, X. Org. Lett. 2019, 21, 3476.
(b) Abengozar, A.; Sucunza, D.; García-García, P.; Sampedro, D.; Perez-Redondo, A.; Vaquero, J. J. Org. Lett. 2019, 21, 2550.
(c) Abengozar, A.; Sucunza, D.; García-García, P.; Sampedro, D.; Perez-Redondo, A.; Vaquero, J. J. J. Org. Chem. 2019, 84, 7113.
(d) Abengozar, A.; García-García, P.; Sucunza, D.; Frutos, L. M.; Castaño, O.; Sampedro, D.; Perez-Redondo, A.; Vaquero, J. J. Org. Lett. 2017, 19, 3458.
(e) Bosdet, M. J. D.; Jaska, C. A.; Piers, W. E.; Sorensen, T. S.; Parvez, M. Org. Lett. 2007, 9, 1395.
(f) Lu, J.; Ko, S.; Walters, N. R.; Kang, Y.; Sauriol, F.; Wang, S. Angew. Chem.. Int. Ed. 2013, 52, 4544.
[13] Ishibashi, J. S. A.; Marshall, J. L.; Maziere, A.; Lovinger, G. J.; Li, B.; Zakharov, L. N.; Dargelos, A.; Graciaa, A.; Chrostowska, A.; Liu, S.-Y. J. Am. Chem. Soc. 2014, 136, 15414.
[14] (a) Kaehler, T.; Bolte, M.; Lerner, H.; Wagner, M. Angew. Chem.. Int. Ed. 2019, 58, 1.
(b) Zhuang, F.-D.; Sun, Z.-H.; Yao, Z.-F.; Chen, Q.-R.; Huang, Z.; Yang, J.-H.; Wang, J.-Y.; Pei, J. Angew. Chem.. Int. Ed. 2019, 58, 1.
(c) Fu, Y.; Zhang, K.; Dmitrieva, E.; Liu, F.; Ma, J.; Weigand, J. J.; Popov, A. A.; Berger, R.; Pisula, W.; Liu, J.; Feng, X. Org. Lett. 2019, 21, 1354.
(d) Li, C.; Liu, Y.; Sun, Z.; Zhang, J.; Liu, M.; Zhang, C.; Zhang, Q.; Wang, J.; Liu, X. Org. Lett. 2018, 20, 2806.
(e) Zhang, J.; Liu, F.; Sun, Z.; Liu, C.; Zhang, Q.; Zhang, C.; Liu, Z.; Liu, X. Chem. Commun. 2018, 54, 8178.
(f) Yang, D.-T.; Nakamura, T.; He, Z.; Wang, X.; Wakamiya, A.; Peng, T.; Wang, S. Org. Lett. 2018, 20, 6741.
[15] (a) Barry, Cook, Haslewood, Hewett, Hieger, Kennaway. Proc. R. Soc. London. Ser. B 1935, 117, 318.
(b) Dou, G.; Shi, D. Chin. J. Org. Chem. 2011, 31, 1989(in Chinese). (窦国兰, 史达清, 有机化学, 2011, 31, 1989.)
(c) Fang, L.; Lin, W. B.; Shen, Y.; Chen, C. Chin. J. Org. Chem. 2018, 38, 541(in Chinese). (房蕾, 林伟彬, 沈赟, 陈传峰, 有机化学, 2018, 38, 541.)
[16] (a) Hatakeyama, T.; Hashimoto, S.; Oba, T.; Nakamura, M. J. Am. Chem. Soc. 2012, 134, 19600.
(b) Matsui, K.; Oda, S.; Yoshiura, K.; Nakajima, K.; Yasuda, N.; Hatakeyama, T. J. Am. Chem. Soc. 2018, 140, 1195.
(c) Nakatsuka, S.; Yasuda, N.; Hatakeyama, T. J. Am. Chem. Soc. 2018, 140, 13562.
(d) Abengózar, A, García-García, P.; Sucunza, D.; Pérez-Redondo, A.; Vaquero, J. J. Chem. Commun. 2018, 54, 2467.
(e) Chen Y.; Chen, W.; Qiao, Y.; Zhou, G. Chem.-Eur. J. 2019, 25, 1.
(f) Shen C, Srebro-Hooper M, Jean M, Vanthuyne, N.; Toupet, L.; Williams, J. A. G.; Torres, A. R.; Riives, A. J.; Muller, G.; Autschbach, J.; Crassous, J. Chem.-Eur. J. 2017, 23, 407.
(g) Sun, Z.; Yi, C.; Liang, Q.; Bingi, C.; Zhu, W.; Qiang, P.; Wu, D.; Zhang, F. Org. Lett. 2020, 22, 209.
(h) Alnoman, R. B.; Rihn, S.; O'Connor, D. C.; Black, F. A.; Costello, B.; Waddlell, P. G.; Clegg, W.; Peacock, R. D.; Herrebout, W.; Knight, J. G.; Hall, M. J. Chem.-Eur. J. 2016, 22, 93.
[17] (a) Allen, F. H.; Kennard, O.; Watson, D. G.; Brammer, L.; Orpen, A. G.; Taylor, R. J. Chem. Soc.. Perkin Trans. 21987, S1.
(b) Abbey, E. R.; Zakharov, L. N.; Liu, S.-Y. J. Am. Chem. Soc. 2008, 130, 7250.
[18] (a) Zi, L.; Zhang, J.; Li, C.; Qu, Y.; Zhen, B.; Liu, X.; Zhang, L. Org. Lett. 2020, 22, 1499.
(b) Zhang, C.; Zhang, L.; Sun, C.; Sun, W.; Liu, X. Org. Lett. 2019, 21, 3476.
(c) Zhang, J.; Liu, F.; Sun, Z.; Li, C.; Zhang, Q.; Zhang, C.; Liu, Z.; Liu, X. Chem. Commun. 2018, 54, 8178.
(d) Li, C.; Liu, Y.; Sun, Z.; Zhang, J.; Liu, M.; Zhang, C.; Zhang, Q.; Wang, H.; Liu, X. Org. Lett. 2018, 20, 2806.
[19] Schleyer, P. V. R.; Maerker, C.; Dransfeld, A.; Jiao, H.; Hommes, N. J. R. E. J. Am. Chem. Soc. 1996, 118, 6317.
[20] Brouwer, A. M. Pure Appl. Chem. 2011, 83, 2213.
[21] Sun, Q.-Y.; Li, Z.; Xu, Z.; Zheng, Z.-J.; Cao, J.; Yang, K.-F.; Cui, Y.-M.; Xu, L.-W. Chem. Commun. 2019, 55, 6229.
[22] (a) Newton, C. G.; Braconi, E.; Cramer, N.; Kuziola, J.; Wodrich, M. D.; Cramer, N. Angew. Chem.. Int. Ed. 2018, 57, 11040.
(b) Couzijn, E. P. A.; van den Engel, D. W. F.; Slootweg, J. C.; de Kanter, F. J. J.; Ehlers, A. W.; Schakel, M.; Lammertsma, K. J. Am. Chem. Soc. 2009, 131, 3741.
[23] (a) Li, W.; Chen, W.; Zhou, B.; Xu, Y.; Deng, B.; Liang, Y.; Yang, Y. Org. Lett. 2019, 21, 8, 2718.
(b) Pierini, A. B.; Baumgartner, M. T.; Rossi, R. A. J. Org. Chem. 1991, 56, 580.

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

PDF

补充材料

可视化

摘要/Abstract

引用此文

分享此文

参考文献

相关文章 15

编辑推荐

相关统计

本文评价

[1]	付雅彤, 孙超凡, 张丹, 金成国, 陆居有. 巢式-碳硼烷硼氢键官能化反应研究进展[J]. 有机化学, 2024, 44(2): 438-447.
[2]	李洋, 董亚楠, 李跃辉. 经由N-硼基酰胺中间体的酰胺高效转化合成腈类化合物[J]. 有机化学, 2024, 44(2): 638-643.
[3]	李思达, 崔鑫, 舒兴中, 吴立朋. 钛催化的烯烃制备1,1-二硼化合物[J]. 有机化学, 2024, 44(2): 631-637.
[4]	马翠云, 罗海澜, 张福华, 郭丹, 陈树兴, 王飞. 3-Pyrrolyl BODIPY的绿色生物合成、光物理性质及应用研究[J]. 有机化学, 2024, 44(1): 216-223.
[5]	陈祖佳, 宇世伟, 周永军, 李焕清, 邱琪雯, 李妙欣, 汪朝阳. BF₃•OEt₂作为催化剂与合成子在有机合成中的应用进展[J]. 有机化学, 2023, 43(9): 3107-3118.
[6]	王文芳. 过渡金属催化不对称C—H硼化反应研究进展[J]. 有机化学, 2023, 43(9): 3146-3166.
[7]	刘露, 张曙光, 胡仁威, 赵晓晓, 崔京南, 贡卫涛. 基于多羟基柱[5]芳烃的酚醛多孔聚合物合成及CO₂催化转化[J]. 有机化学, 2023, 43(8): 2808-2814.
[8]	赵小龙, 郭亮武, 李宇晴, 冉启元, 吴会慧, 张祯, 苏瀛鹏, 周鹏鑫, 燕娜. 大Stokes位移的近红外氟硼二吡咯(BODIPY)荧光探针应用于生物体中Na₂S₂O₄的检测[J]. 有机化学, 2023, 43(7): 2484-2491.
[9]	王莎, 陈常鹏, 曾小明. 联吡啶配体促进铬催化炔烃的顺式硼氢化反应[J]. 有机化学, 2023, 43(7): 2447-2453.
[10]	卢凯, 屈浩琦, 陈樨, 秋慧, 郑晶, 马猛涛. 无催化剂、无溶剂条件下炔烃和烯烃与儿茶酚硼烷的硼氢化反应[J]. 有机化学, 2023, 43(6): 2197-2205.
[11]	刘铃, 浩涛涛, 伍晚花, 杨成. 利用超分子策略构筑具有聚集诱导发光(AIE)功能的二苯乙烯型分子开关[J]. 有机化学, 2023, 43(6): 2189-2196.
[12]	秦玉承, 徐良轩, 徐佳能, 刘超. 1,2-迁移促进的苄基季铵盐硼化反应研究[J]. 有机化学, 2023, 43(5): 1868-1874.
[13]	徐晓阳, 刘美艳, 李成龙, 刘旭光. 1,2-硼氮杂芳烃在中国的研究进展[J]. 有机化学, 2023, 43(5): 1611-1644.
[14]	鲍志成, 李慕尧, 王剑波. 铜催化芳基重氮乙酸酯与双[(频哪醇)硼基]甲烷的偶联反应[J]. 有机化学, 2023, 43(5): 1808-1814.
[15]	刘双, 邹亮华, 王晓明. 均相钴催化氨硼烷的脱氢及转移氢化反应的研究进展[J]. 有机化学, 2023, 43(5): 1713-1725.