Design, Synthesis and Characterization of Gold(I) Compounds with Aggregation-Induced Emission and Reversible Mechanochromism Characteristics

doi:10.6023/cjoc201412008

Chin. J. Org. Chem. ›› 2015, Vol. 35 ›› Issue (3): 681-687.DOI: 10.6023/cjoc201412008 Previous Articles Next Articles

具有聚集诱导发光及机械变色特性的含Au(I)化合物的设计、合成及性质研究

宋敏, 陈钊, 余广鳌, 尹军, 刘盛华

华中师范大学化学学院农药与化学生物学教育部重点实验室武汉 430079

收稿日期:2014-12-03 修回日期:2015-01-13 发布日期:2015-01-23
通讯作者: 刘盛华 E-mail:chshliu@mail.ccnu.edu.cn;yinj@mail.ccnu.edu.cn
基金资助:
国家自然科学基金(Nos. 20931006, 21072070, 21072071, 21272088)和武汉市学科带头人计划(No. 201271130441)资助项目.

Design, Synthesis and Characterization of Gold(I) Compounds with Aggregation-Induced Emission and Reversible Mechanochromism Characteristics

Song Min, Chen Zhao, Yu Guang'ao, Yin Jun, Liu Shenghua

Central China Normal University, College of Chemistry, Key Laboratory of Pesticide and Chemical Biology, Ministry of Education, Wuhan 430079

Received:2014-12-03 Revised:2015-01-13 Published:2015-01-23
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 20931006, 21072070, 21072071, 21272088) and the Program for Academic Leader in Wuhan Municipality (No. 201271130441).

1. Design, Synthesis and Characterization of Gold(I) Compounds with Aggregation-Induced Emission and Reversible Mechanochromism Characteristics.PDF(538KB)

Abstract

Two gold (I) complexes 1 and 2 were designed, synthesized and structurally characterized by NMR, IR as well as elemental analysis. Fluorescence studies show that the two compounds exhibit very weak photoluminescence in pure organic solvents (dimethylsulfoxide or N,N-dimethyl formamide), enhanced fluorescences are observed after the addition of water, which indicate that the aggregation-induced emission (AIE) characteristics of these complexes. The solid-state fluorescence of complexes 1 and 2 can be significantly increased by grinding the solid samples. The recovery of the fluorescence intensity of these ground powders was detected after exposure the samples to organic solvent vapors. This phenomenon suggested the reversible mechanochromism behaviors of comounds 1 and 2. The powder X-ray diffracton (XRD) results displayed the morphology transition between the crystalline and amorphous states before and after the grinding of the sample. The AIE and reversible mechanochromism characteristics of complexes 1 and 2 made them can be potentially used for "smart" materials.

Key words: aggregation-induced emission, mechanochromism, molecular packing state

Cite this article

Song Min, Chen Zhao, Yu Guang'ao, Yin Jun, Liu Shenghua. Design, Synthesis and Characterization of Gold(I) Compounds with Aggregation-Induced Emission and Reversible Mechanochromism Characteristics[J]. Chin. J. Org. Chem., 2015, 35(3): 681-687.

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[1] Pucci, A.; Cuia, F. D.; Signori, F.; Ruggeri, G. J. Mater. Chem. 2007, 17, 783.
[2] Irie, M.; Fukaminato, T.; Sasaki, T.; Tamai, N.; Kawai, T. Nature 2002, 420, 759.
[3] Hirata, S.; Watanabe, T. Adv. Mater. 2006, 18, 2725.
[4] Jakubiak, R.; Collison, C. J.; Wan, W.; Rothberg, L. J.; Hsieh, B. R. J. Phys. Chem. A 1999, 103, 2394.
[5] Toal, S. J.; Jones, K. A.; Magde, D.; Trogler, W. C. J. Am. Chem. Soc. 2005, 127, 11661.
[6] Kinami, M.; Crenshaw, B. R.; Weder, C. Chem. Mater. 2006, 18, 946.
[7] Ning, Z.; Chen, Z.; Zhang, Q.; Yan, Y.; Qian, S.; Cao, Y.; Tian, H. Adv. Funct. Mater. 2007, 17, 3799.
[8] Lim, S. J.; An, B. K.; Jung, S. D.; Chung, M. A.; Park, S. Y. Angew. Chem., Int. Ed. 2004, 43, 6346.
[9] Olson, C. E.; Previte, M. J. R.; Fourkas, J. T. Nat. Mater. 2002, 1, 225.
[10] Dong, Y.; Lam, J. W. Y.; Qin, A.; Liu, J., Li, Z.; Tang, B.; Sun, J.; Kwok, H. S. Appl. Phys. Lett. 2007, 91, 11111.
[11] Kishimura, A.; Yamashita, T.; Y1amaguchi, K.; Aida, T. Nat. Mater. 2005, 4, 546.
[12] Crenshaw, B. R.; Burnworth, M.; Khariwala, D.; Hiltner, A.; Mather, P. T.; Simha, R.; Weder, C. Macromolecules 2007, 40, 2400.
[13] Luo, J.-D.; Xie, Z.-L.; Lam, J. W. Y.; Cheng, L.; Chen, H.-Y.; Qiu, C.-F.; Kwok, H. S.; Zhan, X. W.; Liu, Y. Q.; Zhu, D. B.; Tang, B.-Z. Chem. Commun. 2001, 1740.
[14] Yoon, S. J.; Chung, J. W.; Gierschner, J.; Kim, K. S.; Choi, M. G.; Kim, D.; Park, S. Y. J. Am. Chem. Soc. 2010, 132, 13675.
[15] Qian, L.-J.; Tong, B.; Zhi, J. G.; Yang, F.; Shen, J. B.; Shi, J. B.; Dong, Y. P. Acta Chim. Sinica 2008, 66, 1134 (in Chinese).
(钱立军, 佟斌, 支俊格, 杨帆, 申进波, 石建兵, 董宇平, 化学学报, 2008, 66, 1134.)
[16] Dong, Y.; Xu, B.; Zhang, J.; Tan, X.; Wang, L.; Chen, J.; Lv, H.; Wen, S.; Li, B.; Ye, L.; Zou, B.; Tian, W. Angew. Chem., In. Ed. 2012, 51, 10782.
[17] Ito, H.; Saito, T.; Oshima, N.; Kitamura, N.; Shizaka, S.; Hinatsu, Y.; Wakeshima, M.; Kato, M.; Tauge, K.; Sawamura, M. J. Am. Chem. Soc. 2008, 130, 10044.
[18] Chen, Z.; Zhang, J.; Song M.; Yin, J.; Yu, G. A.; Liu, S. H. Chem. Commun. 2015, 51, 326.
[19] Liang, J. H.; Chen, Z.; Xu, L. J.; Wang, J.; Yin, J.; Yu, G. A.; Chen, Z. N.; Liu, S. H. J. Mater. Chem. C 2014, 2, 2243.
[20] Chen, Z.; Wu, D.; Han, X.; Liang, J. H.; Yin, J.; Yu, G. A.; Liu, S. H. Chem. Commun. 2014, 50, 11033.
[21] Chen, Z.; Liang, J. H.; Han, X.; Yin, J.; Yu, G. A.; Liu, S. H. Dyes Pigm. 2015, 112, 59.
[22] Leoncio, G.; Javier, P.; López-González, M.; Gengwei, Y.; Jianhua F.; Evaristo, R. J. Phys. Chem. B 2012, 116, 11754.
[23] Uson, R.; Laguna, M.; Briggs, D. A.; Murray, H. H.; NFackler, J. P. Inorg. Synth. 1989, 26, 8.
[24] Shan, G. G.; Li, H. B.; S, H. Z.; Zhu, D. X.; Cao, H. T.; Su, Z. M. J. Mater. Chem. C 2013, 1, 1440.

具有聚集诱导发光及机械变色特性的含Au(I)化合物的设计、合成及性质研究

Design, Synthesis and Characterization of Gold(I) Compounds with Aggregation-Induced Emission and Reversible Mechanochromism Characteristics

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