Chiral BINAPO Induced Circularly Polarized Luminescence in a Triple-Stranded Eu2L3(BINAPO)2 Helicate

Shuang Bi; Yanyan Zhou; Yuan Yao; Zhenyu Cheng; Ting Gao; Pengfei Yan; Hongfeng Li

doi:10.1071/CH20074

RESEARCH ARTICLE

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Chiral BINAPO Induced Circularly Polarized Luminescence in a Triple-Stranded Eu₂L₃(BINAPO)₂ Helicate

Shuang Bi

^A , Yanyan Zhou ^A , Yuan Yao ^A , Zhenyu Cheng ^A , Ting Gao

^A ^B , Pengfei Yan ^A and Hongfeng Li ^A ^B

+ Author Affiliations

- Author Affiliations

^A Key Laboratory of Functional Inorganic Material Chemistry (Ministry of Education), School of Chemistry and Materials Science, Heilongjiang University, No. 74, Xuefu Road, Nangang District, Harbin 150080, China.

^B Corresponding authors. Email: gaotingmail@sina.cn; lihongfeng@hlju.edu.cn

Australian Journal of Chemistry 74(2) 145-150 https://doi.org/10.1071/CH20074
Submitted: 5 March 2020 Accepted: 9 June 2020 Published: 9 July 2020

Abstract

Chiral lanthanide helicates with circularly polarized luminescence (CPL) properties have found potential application in bioanalyses and chirality sensing. However, the preparation of the enantiopure helicates through a coordination-directed self-assembly strategy is challenging due to the greatly labile coordination geometries of lanthanide ions. Herein, a pair of enantiopure triple-stranded Eu^III helicates [(Eu₂L₃)(R/S-BINAPO)₂] are assembled by three achiral C₂-symmeric bis-β-diketones (4,4′-bis(4,4,4-trifluoro-1,3-dioxobutyl)(phenoxyl)-1,1′-biphenyl, L) helically twisting around two Eu^III ions, and two chiral R/S-bis(diphenylphosphoryl)-1,1′-binaphthyl (R/S-BINAPO) as ancillary ligands. Electrospray ionization–mass spectrometry, NMR, and circular dichroism (CD) spectra confirm the formation of a pair of enantiopure chiral topological helicates (Eu₂L₃)(R-BINAPO)₂ and (Eu₂L₃)(S-BINAPO)₂. As expected, the helicates present strong CPL with the |g_lum| up to 0.09, and the higher luminescent quantum yields (QYs) of up to 51 %.

References

[1] Y. Imai, Y. Nakano, T. Kawai, J. Yuasa, Angew. Chem. Int. Ed. 2018, 57, 8973.
| Crossref | GoogleScholarGoogle Scholar |

[2] J. Gong, M. Yu, C. Wang, Chem. Commun. 2019, 55, 10768.
| Crossref | GoogleScholarGoogle Scholar |

[3] R. Carr, N. H. Evans, Chem. Soc. Rev. 2012, 41, 7673.
| Crossref | GoogleScholarGoogle Scholar | 22895164PubMed |

[4] G. Muller, Dalton Trans. 2009, 44, 9692.
| Crossref | GoogleScholarGoogle Scholar |

[5] N. P. M. Huck, W. F. Jager, B. de Lange, B. L. Feringa, Science 1996, 273, 1686.
| Crossref | GoogleScholarGoogle Scholar |

[6] F. Zinna, U. Giovanella, L. Di Bari, Adv. Mater. 2015, 27, 1791.
| Crossref | GoogleScholarGoogle Scholar | 25604886PubMed |

[7] C. Wagenknecht, C. M. Li, A. Reingruber, X. H. Bao, A. Goebel, Y. A. Chen, Q. Zhang, K. Chen, J. W. Pan, Nat. Photonics 2010, 4, 549.
| Crossref | GoogleScholarGoogle Scholar |

[8] M. Li, S. H. Li, D. Zhang, M. Cai, L. Duan, M. K. Fung, C. F. Chen, Angew. Chem. Int. Ed. 2018, 57, 2889.
| Crossref | GoogleScholarGoogle Scholar |

[9] J. R. Brandt, X. Wang, Y. Yang, A. J. Campbell, M. J. Fuchter, J. Am. Chem. Soc. 2016, 138, 9743.
| Crossref | GoogleScholarGoogle Scholar | 27434383PubMed |

[10] J. Han, S. Guo, H. Lu, S. Liu, Q. Zhao, W. Huang, Adv. Opt. Mater. 2018, 6, 1800538.
| Crossref | GoogleScholarGoogle Scholar |

[11] F. Zinna, M. Pasini, F. Galeotti, C. Botta, L. Di Bari, U. Giovanella, Adv. Funct. Mater. 2017, 27, 1603719.
| Crossref | GoogleScholarGoogle Scholar |

[12] M. Seitz, E. G. Moore, A. J. Ingram, G. Muller, K. N. Raymond, J. Am. Chem. Soc. 2007, 129, 15468.
| Crossref | GoogleScholarGoogle Scholar | 18031042PubMed |

[13] L. Dai, W. S. Lo, I. D. Coates, R. Pal, G. L. Law, Inorg. Chem. 2016, 55, 9065.
| Crossref | GoogleScholarGoogle Scholar | 27537354PubMed |

[14] Q. Jiang, X. Xu, P. A. Yin, K. Ma, Y. Zhen, P. Duan, Q. Peng, W. Q. Chen, B. Ding, J. Am. Chem. Soc. 2019, 141, 9490.
| Crossref | GoogleScholarGoogle Scholar | 31184485PubMed |

[15] Z. B. Sun, J. K. Liu, D. F. Yuan, Z. H. Zhao, X. Z. Zhu, D. H. Liu, Q. Peng, C. H. Zhao, Angew. Chem. Int. Ed. 2019, 58, 4840.
| Crossref | GoogleScholarGoogle Scholar |

[16] Z. Shen, Y. Sang, T. Wang, J. Jiang, Y. Meng, Y. Jiang, K. Okuro, T. Aida, M. Liu, Nat. Commun. 2019, 10, 3976.
| Crossref | GoogleScholarGoogle Scholar | 31484928PubMed |

[17] D. Yang, P. Duan, L. Zhang, M. Liu, Nat. Commun. 2017, 8, 15727.
| Crossref | GoogleScholarGoogle Scholar | 28585538PubMed |

[18] B. A. San Jose, J. Yan, K. Akagi, Angew. Chem. Int. Ed. 2014, 53, 10641.
| Crossref | GoogleScholarGoogle Scholar |

[19] S. Lee, K. Y. Kim, S. H. Jung, J. H. Lee, M. Yamada, R. Sethy, T. Kawai, J. H. Jung, Angew. Chem. Int. Ed. 2019, 58, 18878.
| Crossref | GoogleScholarGoogle Scholar |

[20] J. R. Jiménez, B. Doistau, C. M. Cruz, C. Besnard, J. M. Cuerva, A. G. Campaña, C. Piguet, J. Am. Chem. Soc. 2019, 141, 13244.
| Crossref | GoogleScholarGoogle Scholar | 31353904PubMed |

[21] R. Aoki, R. Toyoda, J. F. Kögel, R. Sakamoto, J. Kumar, Y. Kitagawa, K. Harano, T. Kawai, H. Nishihara, J. Am. Chem. Soc. 2017, 139, 16024.
| Crossref | GoogleScholarGoogle Scholar | 29046059PubMed |

[22] J. L. Lunkley, D. Shirotani, K. Yamanari, S. Kaizaki, G. Muller, J. Am. Chem. Soc. 2008, 130, 13814.
| Crossref | GoogleScholarGoogle Scholar | 18816117PubMed |

[23] J. Kumar, B. Marydasan, T. Nakashima, T. Kawai, J. Yuasa, Chem. Commun. 2016, 52, 9885.
| Crossref | GoogleScholarGoogle Scholar |

[24] J. C. G. Bünzli, Coord. Chem. Rev. 2015, 293–294, 19.
| Crossref | GoogleScholarGoogle Scholar |

[25] Y. Suffren, B. Golesorkhi, D. Zare, L. Guénée, H. Nozary, S. V. Eliseeva, S. Petoud, A. Hauser, C. Piguet, Inorg. Chem. 2016, 55, 9964.
| Crossref | GoogleScholarGoogle Scholar | 27203270PubMed |

[26] L. Aboshyan-Sorgho, H. Nozary, A. Aebischer, J. C. G. Bünzli, P. Y. Morgantini, K. R. Kittilstved, A. Hauser, S. V. Eliseeva, S. Petoud, C. Piguet, J. Am. Chem. Soc. 2012, 134, 12675.
| Crossref | GoogleScholarGoogle Scholar | 22725838PubMed |

[27] D. Zare, Y. Suffren, H. Nozary, A. Hauser, C. Piguet, Angew. Chem. Int. Ed. 2017, 56, 14612.
| Crossref | GoogleScholarGoogle Scholar |

[28] S. V. Eliseeva, J. C. G. Bünzli, Chem. Soc. Rev. 2010, 39, 189.
| Crossref | GoogleScholarGoogle Scholar | 20023849PubMed |

[29] D. E. Barry, D. F. Caffrey, T. Gunnlaugsson, Chem. Soc. Rev. 2016, 45, 3244.
| Crossref | GoogleScholarGoogle Scholar | 27137947PubMed |

[30] S. E. Howson, P. Scott, Dalton Trans. 2011, 40, 10268.
| Crossref | GoogleScholarGoogle Scholar | 21918779PubMed |

[31] F. Stomeo, C. Lincheneau, J. P. Leonard, J. E. O’Brien, R. D. Peacock, C. P. McCoy, T. Gunnlaugsson, J. Am. Chem. Soc. 2009, 131, 9636.
| Crossref | GoogleScholarGoogle Scholar | 19601680PubMed |

[32] X. Z. Li, L. P. Zhou, L. L. Yan, D. Q. Yuan, C. S. Lin, Q. F. Sun, J. Am. Chem. Soc. 2017, 139, 8237.
| Crossref | GoogleScholarGoogle Scholar | 28558197PubMed |

[33] C. T. Yeung, W. T. K. Chan, S. C. Yan, K. L. Yu, K. H. Yim, W. T. Wong, G. L. Law, Chem. Commun. 2015, 51, 592.
| Crossref | GoogleScholarGoogle Scholar |

[34] Y. Zhou, H. Li, T. Zhu, T. Gao, P. Yan, J. Am. Chem. Soc. 2019, 141, 19634.
| Crossref | GoogleScholarGoogle Scholar | 31747264PubMed |

[35] T. Harada, Y. Nakano, M. Fujiki, M. Naito, T. Kawai, Y. Hasegawa, Inorg. Chem. 2009, 48, 11242.
| Crossref | GoogleScholarGoogle Scholar | 19860395PubMed |

[36] T. Harada, H. Tsumatori, K. Nishiyama, J. Yuasa, Y. Hasegawa, T. Kawai, Inorg. Chem. 2012, 51, 6476.
| Crossref | GoogleScholarGoogle Scholar | 22667353PubMed |

[37] J. Yuasa, T. Ohno, K. Miyata, H. Tsumatori, Y. Hasegawa, T. Kawai, J. Am. Chem. Soc. 2011, 133, 9892.
| Crossref | GoogleScholarGoogle Scholar | 21598978PubMed |

[38] N. Koiso, Y. Kitagawa, T. Nakanishi, K. Fushimi, Y. Hasegawa, Inorg. Chem. 2017, 56, 5741.
| Crossref | GoogleScholarGoogle Scholar | 28448132PubMed |

[39] D. Cotter, S. Dodder, V. J. Klimkowski, T. A. Hopkins, Chirality 2019, 31, 301.
| Crossref | GoogleScholarGoogle Scholar | 30753745PubMed |

[40] S. Wada, Y. Kitagawa, T. Nakanishi, M. Gon, K. Tanaka, K. Fushimi, Y. Chujo, Y. Hasegawa, Sci. Rep. 2018, 8, 16395.
| Crossref | GoogleScholarGoogle Scholar | 30401813PubMed |

[41] Y. Kono, K. Nakabayashi, S. Kitamura, M. Shizuma, M. Fujiki, Y. Imai, RSC Adv. 2016, 6, 40219.
| Crossref | GoogleScholarGoogle Scholar |

[42] Y. Okayasu, J. Yuasa, Mol. Syst. Des. Eng. 2018, 3, 66.
| Crossref | GoogleScholarGoogle Scholar |

[43] M. Górecki, L. Carpita, L. Arrico, F. Zinna, L. Di Bari, Dalton Trans. 2018, 47, 7166.
| Crossref | GoogleScholarGoogle Scholar | 29774898PubMed |

[44] F. Zinna, L. Arrico, L. Di Bari, Chem. Commun. 2019, 55, 6607.
| Crossref | GoogleScholarGoogle Scholar |

[45] M. Leonzio, M. Bettinelli, L. Arrico, M. Monari, L. Di Bari, F. Piccinelli, Inorg. Chem. 2018, 57, 10257.
| Crossref | GoogleScholarGoogle Scholar | 30080030PubMed |

[46] S. G. Telfer, T. M. McLean, M. R. Waterland, Dalton Trans. 2011, 40, 3097.
| Crossref | GoogleScholarGoogle Scholar | 21240395PubMed |

[47] G. Muller, in Luminescence of Lanthanide Ions in Coordination Compounds and Nanomaterials (Ed. A. de Bettencourt-Dias) 2014, pp. 77–124 (Wiley: Hoboken, NJ).

[48] S. D. Bonsall, M. Houcheime, D. A. Straus, G. Muller, Chem. Commun. 2007, 35, 3676.
| Crossref | GoogleScholarGoogle Scholar |

[49] S. Petoud, G. Muller, E. G. Moore, J. Xu, J. Sokolnicki, J. P. Riehl, U. N. Le, S. M. Cohen, K. N. Raymond, J. Am. Chem. Soc. 2007, 129, 77.
| Crossref | GoogleScholarGoogle Scholar | 17199285PubMed |

[50] D. Liu, Y. Zhou, Y. Zhang, H. Li, P. Chen, W. Sun, T. Gao, P. Yan, Inorg. Chem. 2018, 57, 8332.
| Crossref | GoogleScholarGoogle Scholar | 29943980PubMed |

[51] K. T. Hua, J. Xu, E. E. Quiroz, S. Lopez, A. J. Ingram, V. A. Johnson, A. R. Tisch, A. de Bettencourt-Dias, D. A. Straus, G. Muller, Inorg. Chem. 2012, 51, 647.
| Crossref | GoogleScholarGoogle Scholar | 22148725PubMed |

[52] K. Miyata, T. Nakagawa, R. Kawakami, Y. Kita, K. Sugimoto, T. Nakashima, T. Harada, T. Kawai, Y. Hasegawa, Chem. – Eur. J. 2011, 17, 521.
| Crossref | GoogleScholarGoogle Scholar | 21207569PubMed |

[53] F. J. Steemers, W. Verboom, D. N. Reinhoudt, E. B. van der Tol, J. W. Verhoeven, J. Am. Chem. Soc. 1995, 117, 9408.
| Crossref | GoogleScholarGoogle Scholar |

[54] M. Latva, H. Takalo, V. M. Mukkala, C. Matachescu, J. C. Rodriguez-Ubis, J. Kankare, J. Lumin. 1997, 75, 149.
| Crossref | GoogleScholarGoogle Scholar |

Chiral BINAPO Induced Circularly Polarized Luminescence in a Triple-Stranded Eu2L3(BINAPO)2 Helicate

Abstract

References

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Chiral BINAPO Induced Circularly Polarized Luminescence in a Triple-Stranded Eu₂L₃(BINAPO)₂ Helicate