Citation: Wen-Jie Wu, Hong-Xiang Huang, Meng Chen, Dong-Jin Qian. Synthesis and luminescent properties of a silylated-terpyridine derivative and its metalated complexes in solutions and self-assembled monolayers[J]. Chinese Chemical Letters, ;2015, 26(3): 343-347. doi: 10.1016/j.cclet.2014.11.025 shu

Synthesis and luminescent properties of a silylated-terpyridine derivative and its metalated complexes in solutions and self-assembled monolayers

1.
a Department of Chemistry, Fudan University, Shanghai 200433, China;
2.
b State Key Laboratory of Molecular Engineering of Polymers, Fudan University, Shanghai 200433, China

Corresponding author: Dong-Jin Qian,
Received Date: 13 August 2014
Available Online: 13 November 2014
Fund Project: This work was supported by National Natural Science Foundation of China (No. 21373058) (No. 21373058)

A silylated-terpyridine (SiTPy) derivative was newly synthesized and reacted with various transition metal ions in the solutions and self-assembled monolayers (SAMs). Composition and morphology of the SAMs were characterized by using absorption spectra, X-ray photoelectron spectra and atomic force microscope. The silylated-TPy compound gave off a luminescent emission at about 456 nm, which slightly shifted to 452 nm in the Zn²⁺-SiTPy and Fe²⁺-SiTPy metalated complexes. The absorbed energy can be further transferred to lanthanide ions (Tb³⁺ and Eu³⁺) to give off the typical emissions of the lanthanide complexes together with an emission of the silylated-TPy at about 363 nm.
- Silylated-terpyridine,
- Metal complexes,
- Self-assembled monolayer,
- Fluorescence
1. [1]
  [1] A. Wild, A. Winter, F. Schlütter, U.S. Schubert, Advances in the field of π-conjugated 2,2':6',2"-terpyridines, Chem. Soc. Rev. 40 (2011) 1459-1511.
2. [2]
  [2] S.C. Yuan, H.B. Chen, H.C. Wang, Assembly and metal complex properties of terpyridine ligands, Prog. Chem. 21 (2009) 2132-2152.
3. [3]
  [3] N. Tuccitto, I. Delfanti, V. Torrisi, et al., Supramolecular self-assembled multilayers of terpyridine-functionalized perylene bisimide metal complexes, Phys. Chem. Chem. Phys. 11 (2009) 4033-4038.
4. [4]
  [4] C. Mugeman, J.F. Gohy, C.A. Fustin, Functionalized nanoporous thin films from metallo-supramolecular diblock copolymers, Langmuir 28 (2012) 3018-3023.
5. [5]
  [5] C. Haensch, M. Chiper, C. Ulbricht, et al., Reversible supramolecular functionalization of surfaces: terpyridine ligands as versatile building blocks for noncovalent architectures, Langmuir 24 (2008) 12981-12985.
6. [6]
  [6] C.F. Zhang, H.X. Huang, B. Liu, M. Chen, D.J. Qian, Spectroscopic study on the 4'-(4-pyridyl)-2,2':6',2"-terpyridine and its metal complexes, J. Lumin. 128 (2008) 469-475.
7. [7]
  [7] A.P. Duarte, M. Gressier, M.J. Menu, et al., Structural and luminescence properties of silica-based hybrids containing new silylated-diketonato europium(III) complex, J. Phys. Chem. C 116 (2012) 505-515.
8. [8]
  [8] Q.F. Jin, G.X. Liao, S.J. Yu, X.G. Jian, Characterization and tribological investigation of self-assembled trimethoxysilyl-functionalized poly (phthalazinone ether ketone) thin films on glass substrates, Chin. Chem. Lett. 21 (2010) 973-975.
9. [9]
  [9] J.H. Wang, G.S. Hanan, A facile route sterically hindered and non-hindered 4'-aryl-2,2':6',2"-terpyridines, Synlett 8 (2005) 1251-1254.
10. [10]
  [10] L. Hou, D. Li, W.J. Shi, Y.G. Yin, S.W. Ng, Ligand-controlled mixed-valence copper rectangular grid-type coordination polymers based on pyridylterpyridine, Inorg. Chem. 44 (2005) 7825-7832.
11. [11]
  [11] Z. Naseri, A.N. Kharat, A. Banavand, A. Bakhoda, S. Foroutannejad, First now transition metal complexes of thienyl substituted terpyridine: structural, photophysical and biological studies, Polyhedron 33 (2012) 396-403.
12. [12]
  [12] P.F. Shi, Q. Jiang, H.C. Duan, D.Q. Wang, Synthesis, characterization and cytotoxicity of fluorescent organotin complexes of terpyridine derivatives, Chin. Chem. Lett. 25 (2014) 586-588.
13. [13]
  [13] X.M. Xiang, D.J. Qian, H.G. Liu, H.T. Chen, X.S. Feng, Fabrication of europium complexes with 4'-(4-methylphenyl)-2,2':6',2"-terpyridine and 4,40-dinonyl-2,2'-dipyridyl at the air-water interface and their emission properties in Langmuir-Blodgett films, Colloids Surf. A: Physicochem. Eng. Asp. 273 (2006) 29-34.
14. [14]
  [14] T. Ala-Kleme, M. Latva, K. Haapakka, Study on the radiative ⁵D₄→⁷F_j relaxation dynamics of Tb(III) in electrochemically excited self-assembled dimeric heterodinuclear Tb(III)-Ln(III) chelates, Anal. Chim. Acta 403 (2000) 161-171.
15. [15]
  [15] H.G. Liu, X.S. Feng, L.J. Zhang, et al., Influences of hydrophilic and hydrophobic substituents on the organization of supramolecular assemblies of porphyrin derivatives formed at the air/water interface, Mater. Sci. Eng. C 23 (2003) 585-592.
1. [1]
  Deshuai Zhen , Chunlin Liu , Qiuhui Deng , Shaoqi Zhang , Ningman Yuan , Le Li , Yu Liu . A review of covalent organic frameworks for metal ion fluorescence sensing. Chinese Chemical Letters, 2024, 35(8): 109249-. doi: 10.1016/j.cclet.2023.109249
2. [2]
  Zhu Shu , Xin Lei , Yeye Ai , Ke Shao , Jianliang Shen , Zhegang Huang , Yongguang Li . ATP-induced supramolecular assembly based on chromophoric organic molecules and metal complexes. Chinese Chemical Letters, 2024, 35(11): 109585-. doi: 10.1016/j.cclet.2024.109585
3. [3]
  Ying Xu , Chengying Shen , Hailong Yuan , Wei Wu . Mapping multiple phases in curcumin binary solid dispersions by fluorescence contrasting. Chinese Chemical Letters, 2024, 35(9): 109324-. doi: 10.1016/j.cclet.2023.109324
4. [4]
  Hao Zhang , Hao Liu , Ke Huang , Qingxiu Xia , Hongjie Xiong , Xiaohui Liu , Hui Jiang , Xuemei Wang . Ionic exchange based intracellular self-assembly of pitaya-structured nanoparticles for tumor imaging. Chinese Chemical Letters, 2025, 36(6): 110281-. doi: 10.1016/j.cclet.2024.110281
5. [5]
  Manman Ou , Yunjian Zhu , Jiahao Liu , Zhaoxuan Liu , Jianjun Wang , Jun Sun , Chuanxiang Qin , Lixing Dai . Polyvinyl alcohol fiber with enhanced strength and modulus and intense cyan fluorescence based on covalently functionalized graphene quantum dots. Chinese Chemical Letters, 2025, 36(2): 110510-. doi: 10.1016/j.cclet.2024.110510
6. [6]
  Junqing Wu , Yiyang Zhang , Qingqing Hong , Hui Yang , Lifeng Zhang , Ming Zhang , Lei Yu . Organometallic modification of silica with europium endowing the fluorescence properties: The key technique for numerical quality monitoring. Chinese Chemical Letters, 2025, 36(4): 110165-. doi: 10.1016/j.cclet.2024.110165
7. [7]
  Kuan Deng , Fei Yang , Zhi-Qi Cheng , Bi-Wen Ren , Hua Liu , Jiao Chen , Meng-Yao She , Le Yu , Xiao-Gang Liu , Hai-Tao Feng , Jian-Li Li . Construction of wavelength-tunable DSE quinoline salt derivatives by regulating the hybridization form of the nitrogen atom and intramolecular torsion angle. Chinese Chemical Letters, 2024, 35(10): 109464-. doi: 10.1016/j.cclet.2023.109464
8. [8]
  Mengfan Zhang , Lingyan Liu , Peng Wei , Wei Feng , Tao Yi . A proximity tagging strategy utilizing an activated aldehyde group as the active site. Chinese Chemical Letters, 2025, 36(4): 110127-. doi: 10.1016/j.cclet.2024.110127
9. [9]
  Ying Wang , Hong Yang , Caixia Zhu , Qing Hong , Xuwen Cao , Kaiyuan Wang , Yuan Xu , Yanfei Shen , Songqin Liu , Yuanjian Zhang . Cascading oxidoreductases-like nanozymes for high selective and sensitive fluorescent detection of ascorbic acid. Chinese Chemical Letters, 2025, 36(4): 110153-. doi: 10.1016/j.cclet.2024.110153
10. [10]
  Hong Wu , Yuxi Wang , Hongyan Feng , Xiaokui Wang , Bangkun Jin , Xuan Lei , Qianghua Wu , Hongchun Li . Application of Computational Chemistry in the Determination of Magnetic Susceptibility of Metal Complexes. University Chemistry, 2025, 40(3): 116-123. doi: 10.12461/PKU.DXHX202405141
11. [11]
  Wei Su , Xiaoyan Luo , Peiyuan Li , Ying Zhang , Chenxiang Lin , Kang Wang , Jianzhuang Jiang . Phthalocyanine self-assembled nanoparticles for type Ⅰ photodynamic antibacterial therapy. Chinese Chemical Letters, 2024, 35(12): 109522-. doi: 10.1016/j.cclet.2024.109522
12. [12]
  Yihao Zhang , Yang Jiao , Xianchao Jia , Qiaojia Guo , Chunying Duan . Highly effective self-assembled porphyrin MOCs nanomaterials for enhanced photodynamic therapy in tumor. Chinese Chemical Letters, 2024, 35(5): 108748-. doi: 10.1016/j.cclet.2023.108748
13. [13]
  Yuwen Zhu , Xiang Deng , Yan Wu , Baode Shen , Lingyu Hang , Yuye Xue , Hailong Yuan . Formation mechanism of herpetrione self-assembled nanoparticles based on pH-driven method. Chinese Chemical Letters, 2025, 36(1): 109733-. doi: 10.1016/j.cclet.2024.109733
14. [14]
  YanYuan Jia , Rong Rong , Jie Liu , Jing Guo , GuoYu Jiang , Shuo Guo . Unity is Strength, and Independence Shines: A Science Popularization Experiment on AIE and ACQ Effects. University Chemistry, 2024, 39(9): 349-358. doi: 10.12461/PKU.DXHX202402035
15. [15]
  Qin Li , Kexin Yang , Qinglin Yang , Xiangjin Zhu , Xiaole Han , Tao Huang . Illuminating Chlorophyll: Innovative Chemistry Popularization Experiment. University Chemistry, 2024, 39(9): 359-368. doi: 10.3866/PKU.DXHX202309059
16. [16]
  Zehua Zhang , Haitao Yu , Yanyu Qi . 多重共振TADF分子的设计策略. Acta Physico-Chimica Sinica, 2025, 41(1): 2309042-. doi: 10.3866/PKU.WHXB202309042
17. [17]
  Feng Lu , Tao Wang , Qi Wang . Preparation and Characterization of Water-Soluble Silver Nanoclusters: A New Design and Teaching Practice in Materials Chemistry Experiment. University Chemistry, 2025, 40(4): 375-381. doi: 10.12461/PKU.DXHX202406005
18. [18]
  Luyu Zhang , Zirong Dong , Shuai Yu , Guangyue Li , Weiwen Kong , Wenjuan Liu , Haisheng He , Yi Lu , Wei Wu , Jianping Qi . Ionic liquid-based in situ dynamically self-assembled cationic lipid nanocomplexes (CLNs) for enhanced intranasal siRNA delivery. Chinese Chemical Letters, 2024, 35(7): 109101-. doi: 10.1016/j.cclet.2023.109101
19. [19]
  Hao Zhang , Haonan Qu , Ehsan Bahojb Noruzi , Haibing Li , Feng Liang . A nanocomposite film with layer-by-layer self-assembled gold nanospheres driven by cucurbit[7]uril for the selective transport of L-tryptophan and lysozyme. Chinese Chemical Letters, 2025, 36(1): 109731-. doi: 10.1016/j.cclet.2024.109731
20. [20]
  Weiwei Liu , Yu Liu , Zhaoyan Tian , Zhaohan Wang , Hui Liu , Songqin Liu , Yafeng Wu . Online detecting living cells released TNF-α and studying intercellular communication using SuperDNA self-assembled conical nanochannel. Chinese Chemical Letters, 2025, 36(5): 110561-. doi: 10.1016/j.cclet.2024.110561

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(877)
HTML views(76)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142