Synthesis and Properties of Sodium and Europium(Ⅲ) Cryptates Incorporating the 4,4'-Substituted-2,2'-bipyridine Units

doi:10.6023/cjoc201702004

Chin. J. Org. Chem. ›› 2017, Vol. 37 ›› Issue (5): 1198-1204.DOI: 10.6023/cjoc201702004 Previous Articles Next Articles

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4，4'-取代-2，2'-联吡啶钠和铕穴状化合物的合成和性质（英文）

陈素芳^a, 洪玉标^a, 刘元忠^b, 薛明强^a, 郑煜^a, 沈琪^a

a 苏州大学材料与化学化工学部苏州 215123;
b 中国科学院苏州生物医学工程技术研究所中国科学院生物医学诊断重点实验室苏州 215163

收稿日期:2017-02-03 修回日期:2017-03-27 发布日期:2017-04-01
通讯作者: 薛明强 E-mail:xuemingqiang@suda.edu.cn
基金资助:
国家自然科学基金（No.21372171）资助项目.

Synthesis and Properties of Sodium and Europium(Ⅲ) Cryptates Incorporating the 4,4'-Substituted-2,2'-bipyridine Units

Chen Sufang^a, Hong Yubiao^a, Liu Yuanzhong^b, Xue Mingqiang^a, Zheng Yu^a, Shen Qi^a

a College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123;
b CAS Key Laboratory of Bio-Medical Diagnostics, Suzhou Institute of Biomedical Engineering and Technology, Chinese Academy of Sciences, Suzhou 215163

Received:2017-02-03 Revised:2017-03-27 Published:2017-04-01
Contact: 10.6023/cjoc201702004 E-mail:xuemingqiang@suda.edu.cn
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21372171).

1. Synthesis and Properties of Sodium and Europium(Ⅲ) Cryptates Incorporating the 4,4'-Substituted-2,2'-bipyridine Units.PDF(1330KB)

Abstract

A general strategy for the syntheses of 4,4',6,6'-substituted-2,2'-bipyridines starting from aromatic aldehyde is described. A series of sodium cryptates and two europium cryptates [Eu⊂bpy·bpy·bpy]·2Cl·Br (bpy=6,6'-dimethylene-2,2'-bipyridine-4,4'-dimethylester) (23) and [Eu⊂bpy¹·bpy¹·bpy²]·2Cl·Br (bpy¹=6,6'-dimethylene-2,2'-bipyridine-4,4'-dicarboxylic acid, bpy²=6,6'-dimethylene-2,2'-bipyridine-4,4'-diformylethylenediamine) (24), were synthesized from these compounds. Sodium cryptates have been confirmed by ¹H NMR, ¹³C NMR and high resolution mass spectrum (HRMS). The structure of europium cryptate 23 was confirmed by X-ray diffraction (XRD) and HRMS. The photoluminescence (PL) spectra, decay curve and the absolute quantum efficiency (η) of 23 are presented. 23 can be efficiently excited by near-UV light and presents a bright red luminescence with the lifetime (τ) of 0.32 ms and the η of 70%. It is suggested that 23 is expected to be a potential efficient phosphor for lighting and display.

Key words: cryptates, spectroscopy, macrocyclic compounds, phosphor, crystal structure

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Chen Sufang, Hong Yubiao, Liu Yuanzhong, Xue Mingqiang, Zheng Yu, Shen Qi. Synthesis and Properties of Sodium and Europium(Ⅲ) Cryptates Incorporating the 4,4'-Substituted-2,2'-bipyridine Units[J]. Chin. J. Org. Chem., 2017, 37(5): 1198-1204.

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[1] (a) Parker, D. Coord. Chem. Rev. 2000, 205, 109.
(b) Xu, J. D.; Corneillie, T. M.; Moore, E. G.; Law, G.-L.; Butlin, N. G.; Raymond, K. N. J. Am. Chem. Soc. 2011, 133, 19900.
(c) Xi, P.; Xia, H. Y.; Zhao, F. L.; Chen, B. W. Mater. Lett. 2015, 160, 463.
(d) Chai, W. X.; Zhang, X. L.; Song, L.; Hong, M. W.; Shi, H. S.; Wang, C. Y.; Guo, J. Y.; Zheng, X. J.; Chen, G.; Shu, K. Y. Mater. Lett. 2015, 145, 4.
(e) Yang, L. G.; Yu, Y. Z.; Wang, X.; Zhu, M. L.; Gao, Q. Q.; Dai, Y. Q.; Bian, Y. Z. Inorg. Chem. Commun. 2016, 73, 30.
(f) Parbhakar, S.; Gupta, R.; Behera, J. N.; Hussain, F. Inorg. Chem. Commun. 2016, 72, 117.
(g) Liu, Z. H.; Yang, Y. K.; Sun, Z. Z.; Wu, C. F. Opt. Mater. 2016, 62, 1.
(h) Sheelam, A.; Ramanujam, K. Electrochim. Acta 2016, 216, 457.
[2] Havas, F.; Leygue, N.; Danel, M.; Mestre, B.; Galaup, C.; Picard, C. Tetrahedron 2009, 65, 7673.
[3] (a) Patah, A.; Baechle, J.; Grampp, G. Electrochim. Acta 2016, 219, 305.
(b) de Oliveira, T. C.; Santos, H. P.; Lahoud, M. G.; Franco, D. F.; Freire, R. O.; Dutra, J. D. L.; Cuin, A.; de Lima, J. F.; Marques, L. F. J. Lumin. 2017, 181, 196.
(c) Zhang, Y.; Petersen, J. L.; Milsmann, C. J. Am. Chem. Soc. 2016, 138, 13115.
(d) Baumgartner, Y.; Maximilian Klein, Y.; Constable, E. C.; Housecroft, C. E.; Willgert, M. RSC Adv. 2016, 6, 86220.
(e) Armelao, L.; Dell'Amico, D. B.; Bellucci, L.; Bottaro, G.; Labella, L.; Marchetti, F.; Samaritani, S. Polyhedron 2016, 119, 371.
(f) Zavakhina, M. S.; Samsonenko, D. G.; Dybtsev, D. N.; Argent, S. P.; Blake, A. J.; Schroder, M.; Fedin, V. P. Russ. Chem. Bull. 2015, 64, 2908.
[4] (a) Mukkala, V.-M.; Kankare, J. J. HeIv. Chim. Acta 1992, 75, 1578.
(b) Rodriguz-Ubis, J.-C.; Alpha, B.; Plancherel, D.; Lehn, J.-M. HeIv. Chim. Acta 1984, 67, 2264.
(c) Guillaumont, D.; Bazin, H.; Benech, J.-M.; Boyer, M.; Mathis, G. ChemPhysChem 2007, 8, 480.
(d) Havas, F.; Danel, M.; Galaup, C.; Tisnès, P.; Picard, C. Tetrahedron Lett. 2007, 48, 999.
(e) Weng, G. H.; Zhu, B.; Ye, Y.; Li, S. J. Chin. J. Org. Chem. 2015, 35, 309 (in Chinese). (翁官欢, 朱彬, 叶杨, 李世军, 有机化学, 2015, 35, 309.)
[5] (a) Bazin, H.; Trinquet, E.; Mathis, G. Rev. Mol. Biotechnol. 2002, 82, 233.
(b) Alpha, B.; Lehn, J.-M.; Mathis, G. Angew. Chem., Int. Ed. Engl. 1987, 26, 266.
(c) Prat, O.; Lopez, E.; Mathis, G. Anal. Biochem. 1991, 195, 283.
(d) Alpha, B.; Ballardini, R.; Balzani, V.; Lehn, J.-M.; Perathoner, S.; Sabbatini, N. Photochem. Photobiol. 1990, 52, 299.
[6] (a) Lopez, E.; Chypre, C.; Alpha, B.; Mathis, G. Clin. Chem. 1993, 39, 196.
(b) Brunet, E.; Juanes, O.; Rodriguez-Ubis, J. C. Curr. Chem. Biol. 2007, 1, 11.
(c) Nasso, I.; Galaup, C.; Havas, F.; Tisnes, P.; Picard, C.; Laurent, S.; Vander Elst, L.; Muller, R. N. Inorg. Chem. 2005, 44, 8293.
[7] KrÖHnke, F. Synthesis 1976, 1.
[8] Constable, E. C.; Redondo, A. H.; Housecroft, C. E.; Neuburger, M.; Schaffner, S. Dalton Trans. 2009, 6634.
[9] Harding, M. M.; Koert, U.; Lehn, J.-M.; Marquis-Rigault, A.; Piguet, C.; Siegel, J. HeIv. Chim. Acta 1991, 74, 594.
[10] Neises, B.; Steglich, W. Org. Synth. 1985, 63, 183.
[11] (a) Mangalum, A.; Morgan, B. P.; Hanley, J. M.; Jecen, K. M.; McGill, C. J.; Robertson, G. A.; Smith, R. C. Chem. Commun. 2010, 46, 5136.
(b) Liu, P. N.; Chen, Y. C.; Deng, J. G.; Tu, Y. Q. Synthesis 2001, 2078.
[12] Bischof, C.; Wahsner, J.; Scholten, J.; Trosien, S.; Seitz, M. J. Am. Chem. Soc. 2010, 132, 14334.
[13] Bkouche-Waksman, I.; Guilhem, J.; Pascard, C.; Alpha, B.; Deschenaux, R.; Lehn, J.-M. HeIv. Chim. Acta 1991, 74, 1163.
[14] Yuan, B. L.; Huang, Y. L.; Yu, Y. M.; Kim, S. I.; Seo, H. J. Mater. Lett. 2012, 70, 57.
[15] Peng, A. H.; Xie, E. Q.; Jia, C. W.; Jiang, R.; Lin, H. F. Mater. Lett. 2005, 59, 3866.
[16] Qi, S. Y.; Xie, H. D.; Huang, Y. L.; Kim, S. I.; Seo, H. J. Opt. Mater. Express 2014, 4, 190.
[17] Praveen Rao, P. N.; Amini, M.; Li, H. Y.; Habeeb, A. G.; Knaus, E. E. J. Med. Chem. 2003, 46, 4872.
[18] Karrer, P.; Cochand, C.; Neuss, N. Helv. Chim. Acta 1946, 29, 1836.
[19] Alpha, B.; Anklam, E.; Deschenaux, R.; Lehn, J-M.; Pietraskiewiez, M. Helv. Chim. Acta 1988, 71, 1042.

4，4'-取代-2，2'-联吡啶钠和铕穴状化合物的合成和性质（英文）

Synthesis and Properties of Sodium and Europium(Ⅲ) Cryptates Incorporating the 4,4'-Substituted-2,2'-bipyridine Units

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