Tris(Znsalen) cryptand minimizes Znsalen aggregation arising from intermolecular Zn···O interaction

注册 English

Tris(Znsalen) cryptand minimizes Znsalen aggregation arising from intermolecular Zn···O interaction

Jing Lai , Xian-Sheng Ke , Juan Tang , Jun-Long Zhang

Citation: Jing Lai, Xian-Sheng Ke, Juan Tang, Jun-Long Zhang. Tris(Znsalen) cryptand minimizes Znsalen aggregation arising from intermolecular Zn···O interaction[J]. Chinese Chemical Letters, 2015, 26(8): 937-941. doi: 10.1016/j.cclet.2015.04.023 shu

shu

Tris(Znsalen) cryptand minimizes Znsalen aggregation arising from intermolecular Zn···O interaction

通讯作者: Jun-Long Zhang,

基金项目:
This project was supported by the National Scientific Foundation of China (No. 20971007) (No. 20971007)

National Key Basic Research Support Foundation of China (NKBRSFC) (Nos. 2013CB933402, 2015CB856300). (NKBRSFC)

摘要: Exploring the factors to control Znsalen aggregation is of importance to design functional materials in catalysis, optical materials and biological imaging. In this work, we synthesized and characterized four cryptand type triZnsalen complexes and found that cryptand structure could efficiently minimize intermolecular Zn···O interaction. More importantly, encapsulated by PLGA nanoparticles, cryptand triZnsalen 1 displayed visible intracellular fluorescence whereas monomeric Znsalen 5 could not. These results provide a new access to design new luminescent materials with the potential application in optics and biological studies.

关键词:

English

Tris(Znsalen) cryptand minimizes Znsalen aggregation arising from intermolecular Zn···O interaction

1.
a College of Chemistry and Environmental Science, Hebei University, Baoding 071002, China;
2.
b Beijing National Laboratory for Molecular Sciences, State Key Laboratory of Rare Earth Materials Chemistry and Applications, College of Chemistry and Molecular Engineering, Peking University, Beijing 100871, China

Corresponding author: Jun-Long Zhang,

Received Date: 05 February 2015
Available Online: 20 April 2015
Fund Project:

Abstract: Exploring the factors to control Znsalen aggregation is of importance to design functional materials in catalysis, optical materials and biological imaging. In this work, we synthesized and characterized four cryptand type triZnsalen complexes and found that cryptand structure could efficiently minimize intermolecular Zn···O interaction. More importantly, encapsulated by PLGA nanoparticles, cryptand triZnsalen 1 displayed visible intracellular fluorescence whereas monomeric Znsalen 5 could not. These results provide a new access to design new luminescent materials with the potential application in optics and biological studies.

Key words:

1. [1] S.J. Wezenberg, A.W. Kleij, Material applications for salen frameworks, Angew. Chem. Int. Ed. 47 (2008) 2354-2364.[1] S.J. Wezenberg, A.W. Kleij, Material applications for salen frameworks, Angew. Chem. Int. Ed. 47 (2008) 2354-2364.
2. [2] (a) T. Ueno, T. Koshiyama, M. Ohashi, et al., Coordinated design of cofactor and active site structures in development of new protein catalysts, J. Am. Chem. Soc. 127 (2005) 6556-6562; (b) P.F. Wang, Z.R. Hong, Z.Y. Xie, et al., A bis-salicylaldiminato Schiff base and its zinc complex as new highly fluorescent red dopants for high performance organic electroluminescence devices, Chem. Commun. (2003) 1664-1665; (c) L. Rigamonti, F. Demartin, A. Forni, S. Righetto, A. Pasini, Copper(II) complexes of salen analogues with two differently substituted (push-pull) salicylaldehyde moieties. a study on the modulation of electronic asymmetry and nonlinear optical properties, Inorg. Chem. 45 (2006) 10976-10989.[2] (a) T. Ueno, T. Koshiyama, M. Ohashi, et al., Coordinated design of cofactor and active site structures in development of new protein catalysts, J. Am. Chem. Soc. 127 (2005) 6556-6562; (b) P.F. Wang, Z.R. Hong, Z.Y. Xie, et al., A bis-salicylaldiminato Schiff base and its zinc complex as new highly fluorescent red dopants for high performance organic electroluminescence devices, Chem. Commun. (2003) 1664-1665; (c) L. Rigamonti, F. Demartin, A. Forni, S. Righetto, A. Pasini, Copper(II) complexes of salen analogues with two differently substituted (push-pull) salicylaldehyde moieties. a study on the modulation of electronic asymmetry and nonlinear optical properties, Inorg. Chem. 45 (2006) 10976-10989.
3. [3] (a) S. Di Bella, I. Fragala, Two-dimensional characteristics of the second-order nonlinear optical response in dipolar donor-acceptor coordination complexes, New J. Chem. 26 (2002) 285-290; (b) J.L. Zhang, D.K. Garner, L. Liang, D.A. Barrios, Y. Lu, Noncovalent modulation of pH-dependent reactivity of a Mn-salen cofactor in myoglobin with hydrogen peroxide, Chem. Eur. J. 15 (2009) 7481-7489; (c) J.R. Carey, S.K. Ma, T.D. Pfister, et al., A site-selective dual anchoring strategy for artificial metalloprotein design, J. Am. Chem. Soc. 126 (2004) 10812-10813.[3] (a) S. Di Bella, I. Fragala, Two-dimensional characteristics of the second-order nonlinear optical response in dipolar donor-acceptor coordination complexes, New J. Chem. 26 (2002) 285-290; (b) J.L. Zhang, D.K. Garner, L. Liang, D.A. Barrios, Y. Lu, Noncovalent modulation of pH-dependent reactivity of a Mn-salen cofactor in myoglobin with hydrogen peroxide, Chem. Eur. J. 15 (2009) 7481-7489; (c) J.R. Carey, S.K. Ma, T.D. Pfister, et al., A site-selective dual anchoring strategy for artificial metalloprotein design, J. Am. Chem. Soc. 126 (2004) 10812-10813.
4. [4] C.R. Bhattacharjee, G. Das, P. Mondal, S.K. Prasad, D.S.S. Rao, Novel green light emitting nondiscoid liquid crystalline zinc(II) Schiff-base complexes, Eur. J. Inorg. Chem. 2011 (2011) 1418-1424.[4] C.R. Bhattacharjee, G. Das, P. Mondal, S.K. Prasad, D.S.S. Rao, Novel green light emitting nondiscoid liquid crystalline zinc(II) Schiff-base complexes, Eur. J. Inorg. Chem. 2011 (2011) 1418-1424.
5. [5] G.F. Qi, Z.Y. Yang, B.D. Wang, Synthesis, characterization and DNA-binding properties of zinc(II) and nickel(II) Schiff base complexes, Transit. Met. Chem. 32 (2007) 233-239.[5] G.F. Qi, Z.Y. Yang, B.D. Wang, Synthesis, characterization and DNA-binding properties of zinc(II) and nickel(II) Schiff base complexes, Transit. Met. Chem. 32 (2007) 233-239.
6. [6] (a) J. Jing, J.L. Zhang, Combining myeloperoxidase (MPO) with fluorogenic ZnSalen to detect lysosomal hydrogen peroxide in live cells, Chem. Sci. 4 (2013) 2947-2952; (b) J.J. Chen, J. Jing, H. Chang, et al., A sensitive and quantitative autolysosome probe for detecting autophagic activity in live and prestained fixed cells, Autophagy 9 (2013) 894-904.[6] (a) J. Jing, J.L. Zhang, Combining myeloperoxidase (MPO) with fluorogenic ZnSalen to detect lysosomal hydrogen peroxide in live cells, Chem. Sci. 4 (2013) 2947-2952; (b) J.J. Chen, J. Jing, H. Chang, et al., A sensitive and quantitative autolysosome probe for detecting autophagic activity in live and prestained fixed cells, Autophagy 9 (2013) 894-904.
7. [7] Y. Hai, J.J. Chen, P. Zhao, et al., Luminescent zinc salen complexes as single and two-photon fluorescence subcellular imaging probes, Chem. Commun. 47 (2011) 2435-2437.[7] Y. Hai, J.J. Chen, P. Zhao, et al., Luminescent zinc salen complexes as single and two-photon fluorescence subcellular imaging probes, Chem. Commun. 47 (2011) 2435-2437.
8. [8] (a) J. Jing, J. Tang, D. Xie, et al., Design of luminescent ZnSalen for molecular imaging, Sci. Sin. Chim. 44 (2014) 191-203; (b) Y.B. Cai, J. Zhan, Y. Hai, J.L. Zhang, Molecular assembly directed by metal-aromatic interactions: control of the aggregation and photophysical properties of Zn-salen complexes by aromatic mercuration, Chem. Eur. J. 18 (2012) 4242-4249; (c) J. Tang, Y.B. Cai, J. Jing, J.L. Zhang, Unravelling the correlation betweenmetal induced aggregation and cellular uptake/subcellular localization of Znsalen: an overlooked rule for design of luminescent metal probes, Chem. Sci. 6 (2015) 2389-2397.[8] (a) J. Jing, J. Tang, D. Xie, et al., Design of luminescent ZnSalen for molecular imaging, Sci. Sin. Chim. 44 (2014) 191-203; (b) Y.B. Cai, J. Zhan, Y. Hai, J.L. Zhang, Molecular assembly directed by metal-aromatic interactions: control of the aggregation and photophysical properties of Zn-salen complexes by aromatic mercuration, Chem. Eur. J. 18 (2012) 4242-4249; (c) J. Tang, Y.B. Cai, J. Jing, J.L. Zhang, Unravelling the correlation betweenmetal induced aggregation and cellular uptake/subcellular localization of Znsalen: an overlooked rule for design of luminescent metal probes, Chem. Sci. 6 (2015) 2389-2397.
9. [9] S.S. Sun, C.L. Stern, S.T. Nguyen, J.T. Hupp, Directed assembly of transition-metalcoordinated molecular loops and squares from salen-type components. Examples of metalation-controlled structural conversion, J. Am. Chem. Soc. 126 (2004) 6314-6326.[9] S.S. Sun, C.L. Stern, S.T. Nguyen, J.T. Hupp, Directed assembly of transition-metalcoordinated molecular loops and squares from salen-type components. Examples of metalation-controlled structural conversion, J. Am. Chem. Soc. 126 (2004) 6314-6326.
10. [10] S. Akine, T. Taniguchi, T. Nabeshima, Helical metallohost-guest complexes via site-selective transmetalation of homotrinuclear complexes, J. Am. Chem. Soc. 128 (2006) 15765-15774.[10] S. Akine, T. Taniguchi, T. Nabeshima, Helical metallohost-guest complexes via site-selective transmetalation of homotrinuclear complexes, J. Am. Chem. Soc. 128 (2006) 15765-15774.
11. [11] O. Kotova, K. Lyssenko, A. Rogachev, et al., Low temperature X-ray diffraction analysis, electronic density distribution and photophysical properties of bidentate N,O-donor salicylaldehyde Schiff bases and zinc complexes in solid state, J. Photochem. Photobiol. A Chem. 218 (2011) 117-129.[11] O. Kotova, K. Lyssenko, A. Rogachev, et al., Low temperature X-ray diffraction analysis, electronic density distribution and photophysical properties of bidentate N,O-donor salicylaldehyde Schiff bases and zinc complexes in solid state, J. Photochem. Photobiol. A Chem. 218 (2011) 117-129.
12. [12] G. Consiglio, S. Failla, P. Finocchiaro, I.P. Oliver, S.D. Bella, Aggregation properties of bis(salicylaldiminato)zinc(II) Schiff-base complexes and their Lewis acidic character, Dalton Trans. 41 (2012) 387-395.[12] G. Consiglio, S. Failla, P. Finocchiaro, I.P. Oliver, S.D. Bella, Aggregation properties of bis(salicylaldiminato)zinc(II) Schiff-base complexes and their Lewis acidic character, Dalton Trans. 41 (2012) 387-395.
13. [13] G. Consiglio, S. Failla, P. Finocchiaro, et al., Supramolecular aggregation/deaggregation in amphiphilic dipolar Schiff-base zinc(II) complexes, Inorg. Chem. 49 (2010) 5134-5142.[13] G. Consiglio, S. Failla, P. Finocchiaro, et al., Supramolecular aggregation/deaggregation in amphiphilic dipolar Schiff-base zinc(II) complexes, Inorg. Chem. 49 (2010) 5134-5142.
14. [14] S. Akine, S.J. Piao, M. Miyashita, T. Nabeshima, Cage-like tris(salen)-type metallocryptand for cooperative guest recognition, Tetrahedron Lett. 54 (2013) 6541-6544.[14] S. Akine, S.J. Piao, M. Miyashita, T. Nabeshima, Cage-like tris(salen)-type metallocryptand for cooperative guest recognition, Tetrahedron Lett. 54 (2013) 6541-6544.
15. [15] C.A. Strassert, L.E. Dicelio, J. Awruch, Reduction of an amido zinc(II) phthalocyanine by diborane, Synthesis (2006) 799-802.[15] C.A. Strassert, L.E. Dicelio, J. Awruch, Reduction of an amido zinc(II) phthalocyanine by diborane, Synthesis (2006) 799-802.
16. [16] A. Heaton, M. Hill, F. Drakesmith, Polyhalogenonitrobenzenes and derived compounds Part 5. Improved preparations of 1,2,3,4-tetrafluoro-5,6-dinitrobenzene and 3,4,5,6-tetrafluoro-1,2-phenylenediamine, and the use of the latter for the synthesis of tetrafluorobenzheterocycles, J. Fluor. Chem. 81 (1997) 133-138.[16] A. Heaton, M. Hill, F. Drakesmith, Polyhalogenonitrobenzenes and derived compounds Part 5. Improved preparations of 1,2,3,4-tetrafluoro-5,6-dinitrobenzene and 3,4,5,6-tetrafluoro-1,2-phenylenediamine, and the use of the latter for the synthesis of tetrafluorobenzheterocycles, J. Fluor. Chem. 81 (1997) 133-138.
17. [17] K. Li, J. Pan, S.S. Feng, et al., Generic strategy of preparing fluorescent conjugatedpolymer-loaded poly(DL-lactide-co-glycolide) nanoparticles for targeted cell imaging, Adv. Funct. Mater. 19 (2009) 3535-3542.[17] K. Li, J. Pan, S.S. Feng, et al., Generic strategy of preparing fluorescent conjugatedpolymer-loaded poly(DL-lactide-co-glycolide) nanoparticles for targeted cell imaging, Adv. Funct. Mater. 19 (2009) 3535-3542.
18. [18] D.N. Kumar, B.S. Garg, Synthesis and spectroscopic studies of complexes of zinc(II) with N₂O₂ donor groups, Spectrochim. Acta A Mol. Biomol. Spectrosc. 64 (2006) 141-147.[18] D.N. Kumar, B.S. Garg, Synthesis and spectroscopic studies of complexes of zinc(II) with N₂O₂ donor groups, Spectrochim. Acta A Mol. Biomol. Spectrosc. 64 (2006) 141-147.

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