Chinese Journal of Organic Chemistry >
Triple Aza[6]helicenes with Circularly Polarized Luminescence: N-Alkylation as a Tool to Tune the Chiroptical Properties
Received date: 2024-05-07
Revised date: 2024-05-17
Online published: 2024-05-23
Supported by
National Natural Science Foundation of China(22171044)
Recently, multiple helicenes have attracted enormous attention due to their exceptionally distorted conjugated architectures, appealing optical properties and unique spatial stacking patterns. The electronic and optical properties of multiple helicenes could be modulated by heteroatom doping. Herein, the first triple aza[6]helicene was reported by an intramolecular oxidation reaction, which exhibited highly distorted propeller-like geometry revealed by single crystal X-ray diffraction analysis. In comparison to the reported triple oxa[6]helicene, the triple aza[6]helicene demonstrated increased quantum yield (5.5%), and chiroptical properties with a |gabs| value of 0.012 and a |glum| value of 3.0×10－3. Furthermore, the stability and chiroptical properties of the triple aza[6]helicene could be enhanced by N-alkylation.
Yufei Xia , Li Jiang , Qiao Yang , Xiu Yu , Fengkun Chen . Triple Aza[6]helicenes with Circularly Polarized Luminescence: N-Alkylation as a Tool to Tune the Chiroptical Properties[J]. Chinese Journal of Organic Chemistry, 2024 , 44(9) : 2841 -2846 . DOI: 10.6023/cjoc202405006
| [1] | Petrukhina, M. A.; Scott, L. T. Fragments of Fullerenes and Carbon Nanotubes: Designed Synthesis, Unusual Reactions, and Coordination Chemistry, Wiley, Hoboken, New Jersey, 2011. |
| [2] | (a) Pun, S. H.; Miao, Q. Acc. Chem. Res. 2018, 51, 1630. |
| [2] | (b) Chao, L.; Stepek, I. A.; Yamada, K. E.; Ito, H.; Itami, K. Angew. Chem., Int. Ed. 2021, 60, 23508. |
| [2] | (c) Majewski, M. A.; St?pień, M. Angew. Chem., nt. Ed. 2019, 58, 86. |
| [3] | (a) Shen, Y.; Chen, C.-F. Chem. Rev. 2012, 112, 1463. |
| [3] | (b) Gingras, M. Chem. Soc. Rev. 2013, 42, 968. |
| [3] | (c) Crassous, J.; Stará, I. G.; Stary, I. Helicenes: Synthesis, Properties and Applications, Wiley-VCH, Weinheim, 2022. |
| [4] | (a) Fang, L.; Lin, W.; Shen, Y.; Chen, C.-F. Chin. J. Org. Chem. 2018, 38, 541 (in Chinese). |
| [4] | (房蕾, 林伟彬, 沈赟, 陈传峰, 有机化学, 2018, 38, 541.) |
| [4] | (b) Narcis, M. J.; Takenaka, N. Eur. J. Org. Chem. 2014, 2014, 21. |
| [5] | (a) Zhao, W.-L.; Li, M.; Lu, H.-Y.; Chen, C.-F. Chem. Commun. 2019, 55, 13793. |
| [5] | (b) Mori, T. Chem. Rev. 2021, 121, 2373. |
| [6] | (a) Shen, C.; Gan, F.; Zhang, G.; Ding, Y.; Wang, J.; Wang, R.; Crassous, J.; Qiu, H. Mater. Chem. Front. 2020, 4, 837. |
| [6] | (b) Kubo, H.; Hirose, T.; Nakashima, T.; Kawai, T.; Hasegawa, J.-Y.; Matsuda, K. J. Phys. Chem. Lett. 2021, 12, 686. |
| [6] | (c) Shen, Y.-J.; Yao, N.-T.; Diao, L.-N.; Yang, Y.; Chen, X.-L.; Gong, H.-Y. Angew. Chem., nt. Ed. 2023, 62, e202300840. |
| [6] | (d) Huo, G.-F.; Xu, W.-T.; Han, Y.; Zhu, J.; Hou, X.; Fan, W.; Ni, Y.; Wu, S.; Yang, H.-B.; Wu, J. Angew. Chem., nt. Ed. 2024, 63, e202403149. |
| [7] | (a) Kiran, V.; Mathew, S. P.; Cohen, S. R.; Hernández Delgado, I.; Lacour, J.; Naaman, R. Adv. Mater. 2016, 28, 1957. |
| [7] | (b) Pan, T.-R.; Guo, A.-M.; Sun, Q.-F. Phys. Rev. B 2016, 94, 235448. |
| [7] | (c) Kettner, M.; Maslyuk, V. V.; Nürenberg, D.; Seibel, J.; Gutierrez, R.; Cuniberti, G.; Ernst, K.-H.; Zacharias, H. J. Phys. Chem. Lett. 2018, 9, 2025. |
| [7] | (d) Rodríguez, R.; Naranjo, C.; Kumar, A.; Matozzo, P.; Das, T. K.; Zhu, Q.; Vanthuyne, N.; Gómez, R.; Naaman, R.; Sánchez, L.; Crassous, J. J. Am. Chem. Soc. 2022, 144, 7709. |
| [8] | (a) Li, C.; Yang, Y.; Miao, Q. Chem.-Asian J. 2018, 13, 884. |
| [8] | (b) Wu, Y.-F.; Zhang, L.; Zhang, Q.; Xie, S.-Y.; Zheng, L.-S. Org. Chem. Front. 2022, 9, 4726. |
| [9] | (a) Zhu, Y.; Xia, Z.; Cai, Z.; Yuan, Z.; Jiang, N.; Li, T.; Wang, Y.; Guo, X.; Li, Z.; Ma, S.; Zhong, D.; Li, Y.; Wang, J. J. Am. Chem. Soc. 2018, 140, 4222. |
| [9] | (b) Chen, F.; Gu, W.; Saeki, A.; Melle-Franco, M.; Mateo-Alonso, A. Org. Lett. 2020, 22, 3706. |
| [9] | (c) Artigas, A.; Rigoulet, F.; Giorgi, M.; Hagebaum-Reignier, D.; Carissan, Y.; Coquerel, Y. J. Am. Chem. Soc. 2023, 145, 15084. |
| [10] | Hosokawa, T.; Takahashi, Y.; Matsushima, T.; Watanabe, S.; Kikkawa, S.; Azumaya, I.; Tsurusaki, A.; Kamikawa, K. J. Am. Chem. Soc. 2017, 139, 18512. |
| [11] | (a) Tanaka, H.; Ikenosako, M.; Kato, Y.; Fujiki, M.; Inoue, Y.; Mori, T. Commun. Chem. 2018, 1, 38. |
| [11] | (b) Niu, W.; Fu, Y.; Qiu, Z.-L.; Schürmann, C. J.; Obermann, S.; Liu, F.; Popov, A. A.; Komber, H.; Ma, J.; Feng, X. J. Am. Chem. Soc. 2023, 145, 26824. |
| [12] | Yang, W.-W.; Shen, J.-J. Chem.-Eur. J. 2022, 28, e202202069. |
| [13] | (a) Guo, X.; Yuan, Z.; Zhu, Y.; Li, Z.; Huang, R.; Xia, Z.; Zhang, W.; Li, Y.; Wang, J. Angew. Chem., nt. Ed. 2019, 58, 16966. |
| [13] | (b) Li, J.-K.; Chen, X.-Y.; Guo, Y.-L.; Wang, X.-C.; Sue, A. C. H.; Cao, X.-Y.; Wang, X.-Y. J. Am. Chem. Soc. 2021, 143, 17958. |
| [13] | (c) Zhang, L.; Chen, S.; Jiang, J.; Dong, X.; Cai, Y.; Zhang, H.-J.; Lin, J.; Jiang, Y.-B. Org. Lett. 2022, 24, 3179. |
| [13] | (d) Tan, D.; Dong, J.; Ma, T.; Feng, Q.; Wang, S.; Yang, D.-T. Angew. Chem., Int. Ed. 2023, 62, e202304711. |
| [13] | (e) Sun, Z.; Xu, W.; Qiu, S.; Ma, Z.; Li, C.; Zhang, S.; Wang, H. Chem. Sci. 2024, 15, 1077. |
| [14] | (a) Feng, X.; Wu, J.; Enkelmann, V.; Müllen, K. Org. Lett. 2006, 8, 1145. |
| [14] | (b) Feng, X.; Wu, J.; Ai, M.; Pisula, W.; Zhi, L.; Rabe, J. P.; Müllen, K. Angew. Chem., nt. Ed. 2007, 46, 3033. |
| [14] | (c) Liu, Y.; Marszalek, T.; Müllen, K.; Pisula, W.; Feng, X. Chem.- Asian J. 2016, 11, 2107. |
| [15] | Liu, J.; Jiang, L.; Chang, H.; Liu, H.; Cao, X.-Y.; Zou, Y.; Hu, Y. Chem. Commun. 2022, 58, 13087. |
| [16] | (a) Chen, F.; Hong, Y. S.; Shimizu, S.; Kim, D.; Tanaka, T.; Osuka, A. Angew. Chem., nt. Ed. 2015, 54, 10639. |
| [16] | (b) Chen, F.; Hong, Y. S.; Kim, D.; Tanaka, T.; Osuka, A. ChemPlusChem 2017, 82, 1048. |
| [16] | (c) Matsuo, Y.; Chen, F.; Kise, K.; Tanaka, T.; Osuka, A. Chem. Sci. 2019, 10, 11006. |
| [17] | Zhou, F.; Huang, Z.; Huang, Z.; Cheng, R.; Yang, Y.; You, J. Org. Lett. 2021, 23, 4559. |
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