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Triphenylamine pyridine acetonitrile fluorogens with green emission for pH sensing and application in cells |
Chang-Cheng Wanga, Sheng-Yong Yana, Yu-Qi Chena, Yi-Min Zhoua, Cheng Zhonga, Pu Guoa, Rong Huanga, Xiao-Cheng Wenga, Xiang Zhoua,b |
a College of Chemistry and Molecular Sciences, Key Laboratory of Biomedical Polymers of Ministry of Education, Wuhan University, Wuhan 430072, China;
b State Key Laboratory of Natural and Biomimetic Drugs, Peking University, Beijing 100191, China |
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Abstract In this work, triphenylamine pyridine acetonitrile compounds PyA1, PyA2 and PyA3 are designed and synthesized. They show green fluorescence in water and bright emission in solid state. They have large Strokes shift (about 100 nm). The excitation and emission spectra are investigated in ethyl acetate, chloroform, cyclohexane, ethanol, water, acetonitrile, THF, DMF and DMSO. It is interesting to find that these compounds are able to sense increasing pH values ranging from pH 2 to 7 by showing different color and emission intensities: almost no emission at pH 2 and strong green emission at pH 7. The acid-base switched color and fluorescence changes can be observed under UV irradiation, in water solution and 1% agarose gel. These changes can be repeated for several cycles. We are able to employ these compounds for cell pH environment imaging.
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Received: 19 June 2014
Published: 24 November 2014
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Fund: Thisworkwas supported by theNational Basic Research Program of China (973 Program) (Nos. 2012CB720600, 2012CB720603), the National Science Foundation of China (Nos. 91213302, 81373256, 21272181), the National Grand Program on Key Infectious Disease (No. 2012ZX10003002-014), the Program for Changjiang Scholars and Innovative Research Team in University ([62_TD$DIFFF]IF$DTD8_[5]No. IRT1030), and by the Fundamental Research Funds for the Central Universities. |
Corresponding Authors:
Xiang Zhou
E-mail: xzhou@whu.edu.cn
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[1] |
N. Leclerc, S. Sanaur, L. Galmiche, et al., 6-(Arylvinylene)-3-bromopyridine derivatives as lego building blocks for liquid crystal, nonlinear optical, and blue light emitting chromophores, Chem. Mater. 3 (2005) 502-513.
|
[2] |
J. Morin, N. Drolet, Y. Tao, M. Leclerc, Syntheses and characterization of electroactive and photoactive 2,7-carbazolenevinylene-based conjugated oligomers and polymers, Chem. Mater. 23 (2004) 4619-4626.
|
[3] |
M.S. Wong, Z.H. Li, Y. Tao, M. D'Iorio, Synthesis and functional properties of donor-acceptor π-conjugated oligomers, Chem. Mater 5 (2003) 1198-1203.
|
[4] |
W. Zhang, Z. He, Y. Wang, et al., Non-doped red or blue electroluminescent materials based on fluorenyl-triarylamines with fumaronitrile or fluorene bridge, Thin. Solid Films 7 (2012) 2794-2799.
|
[5] |
B. An, S. Kwon, S. Jung, S.Y. Park, Enhanced emission and its switching in fluorescent organic nanoparticles, J. Am. Chem. Soc. 48 (2002) 14410-14415.
|
[6] |
J. Luo, Z. Xie, J.W. Lam, et al., Aggregation-induced emission of 1-methyl-1,2,3,4,5-pentaphenylsilole, Chem. Commun. 18 (2001) 1740-1741.
|
[7] |
Y. Liu, X. Tao, F. Wang, et al., Aggregation-induced emissions of fluorenonearylamine derivatives: a new kind of materials for nondoped red organic lightemitting diodes, J. Phys. Chem. C 10 (2008) 3975-3981.
|
[8] |
D.U. Kim, S.H. Paik, S. Kim, T. Tsutsui, Design and synthesis of a novel red electroluminescent dye, Synth. Met. 1 (2001) 43-46.
|
[9] |
C.L. Chiang, M.F. Wu, D.C. Dai, et al., Red-emitting fluorenes as efficient emitting hosts for non-doped, organic red-light-emitting diodes, Adv. Funct. Mater. 15 (2005) 231-238.
|
[10] |
L. Chen, Y. Cui, X. Mei, et al., Synthesis and characterization of triphenylaminosubstituted chromophores for nonlinear optical applications, Dyes Pigments 3 (2007) 293-298.
|
[11] |
B. Li, Q. Li, B. Liu, et al., The synthesis and photoluminescence characteristics of novel α,β-diarylacrylonitrile derivatives containing both a biphenyl group and a triphenylamine unit, Dyes Pigments 3 (2011) 301-306.
|
[12] |
C. Allain, F. Schmidt, R. Lartia, et al., Vinyl-pyridinium triphenylamines: novel farred emitters with high photostability and two-photon absorption properties for staining DNA, ChemBioChem 4 (2007) 424-433.
|
[13] |
T.C. Lin, W.L. Lin, C.M. Wang, C.W. Fu, Synthesis and characterization of highly soluble two-photon-absorbing chromophores with multi-branched and dendritic architectures, Eur. J. Org. Chem. 5 (2011) 912-921.
|
[14] |
B. Wang, Y. Wang, J. Hua, et al., Starburst triarylamine donor-acceptor-donor quadrupolar derivatives based on cyano-substituted diphenylaminestyrylbenzene: tunable aggregation-induced emission colors and large two-photon absorption cross sections, Chem. Eur. J. 9 (2011) 2647-2655.
|
[15] |
S.J.K. Pond, M. Rumi, M.D. Levin, et al., One-and two-photon spectroscopy of donor-acceptor-donor distyrylbenzene derivatives: effect of cyano substitution and distortion from planarity, J. Phys. Chem. A 47 (2002) 11470-11480.
|
[16] |
K. Panthi, R.M. Adhikari, T.H. Kinstle, Aromatic fumaronitrile core-based donor-linker-acceptor-linker-donor (D-p-A-p-D) compounds: synthesis and photophysical properties, J. Phys. Chem. A 13 (2010) 4542-4549.
|
[17] |
R. Huang, S. Yan, X. Zheng, et al., Development of a pH-activatable fluorescent probe and its application for visualizing cellular pH change, Analyst 19 (2012) 4418-4420.
|
[18] |
F. Galindo, M.I. Burguete, L. Vigara, et al., Synthetic macrocyclic peptidomimetics as tunable pH probes for the fluorescence imaging of acidic organelles in live cells, Angew. Chem. Int. Ed. Engl. 40 (2005) 6504-6508.
|
[19] |
H. Lu, B. Xu, Y. Dong, et al., Novel fluorescent pH sensors and a biological probe based on anthracene derivatives with aggregation-induced emission characteristics, Langmuir 9 (2010) 6838-6844.
|
[20] |
D. Cui, X. Qian, F. Liu, R. Zhang, Novel fluorescent pH sensors based on intramolecular hydrogen bonding ability of naphthalimide, Org. Lett. 16 (2004) 2757-2760.
|
[21] |
B. Tang, X. Liu, K. Xu, et al., A dual near-infrared pH fluorescent probe and its application in imaging of HepG2 cells, Chem. Commun. 36 (2007) 3726-3728.
|
[22] |
T. Mallegol, S. Gmouth, M. Meziane, et al., Practical and efficient synthesis of tris(4-formylphenyl)amine, a key building block in materials chemistry, Synthesis 11 (2005) 1771-1774.
|
[23] |
H. Lai, Y.J. Xiao, S.Y. Yan, et al., Symmetric cyanovinyl-pyridinium triphenylamine: a novel fluorescent switch-on probe for an antiparallel G-quadruplex, Analyst 139 (2014) 1834-1838.
|
[24] |
G.W. Trucks, M.J. Frisch, H.B. Schlegel, et al., Gaussian 09, Revision A 02 ed., Gaussian Inc., Wallingford, CT, 2009.
|
[25] |
S.J. Chen, J.Z. Liu, Y. Liu, et al., An AIE-active hemicyanine fluorogen with stimuliresponsive red/blue emission: extending the pH sensing range by "switch + -knob" effect, Chem. Sci. 3 (2012) 1804-1809.
|
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