Abstract
A cyano-substituted diarylethlene derivative aggregation-induced emission (AIE) dye with two amino end-groups and 4,4′-(hexafluoroisopropylidene)diphthalic anhydride were facilely incorporated into red fluorescent organic nanoparticles (FONs) via room temperature anhydride ring-opening polymerization under an air atmosphere. These obtained RO-HFDA FONs were characterized by a series of techniques including gel permeation chromatography, Fourier transform infrared spectroscopy, size distribution and zeta potential measurements, UV-Vis absorption spectrum, fluorescent spectroscopy and transmission electron microscopy. Biocompatibility evaluation and cell uptake behavior of RO-HFDA FONs were further investigated to explore their potential biomedical application. We demonstrated that such FONs showed high water dispersibility, stable uniform spherical morphology (150–200 nm), broad excitation band (350–605 nm), intense red fluorescence (627 nm) and excellent biocompatibility, making them promising for cell imaging applications.
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Kumar, V., Adamson, D.H. and Prud’homme, R.K., Small, 2010, 6: 2907
Nehilla, B.J., Allen, P.G. and Desai, T.A., ACS nano, 2008, 2: 538
Patlolla, R.R., Desai, P.R., Belay, K. and Singh, M.S., Biomaterials, 2010, 31: 5598
Ho, Y.P. and Leong, K.W., Nanoscale, 2010, 2: 60
Chandra, S., Das, P., Bag, S., Laha, D. and Pramanik, P., Nanoscale, 2011, 3: 1533
Shiohara, A., Prabakar, S., Faramus, A., Hsu, C.Y., Lai, P.S., Northcote, P.T. and Tilley, R.D., Nanoscale, 2011, 3: 3364
Vollrath, A., Schubert, S. and Schubert, U.S., J. Mater. Chem. B, 2013, 1: 1994
Grazon, C., Rieger, J., Méallet-Renault, R., Charleux, B. and Clavier, G., Macromolecules, 2013, 46: 5167
Hong, Y., Lam, J.W. and Tang, B.Z., Chem. Soc. Rev., 2011, 40: 5361
Hong, Y., Lam, J.W.Y. and Tang, B.Z., Chem. Commun., 2009 4332
Luo, J., Xie, Z., Lam, J.W.Y., Cheng, L., Chen, H., Qiu, C., Kwok, H.S., Zhan, X., Liu, Y., Zhu, D. and Tang, B.Z., Chem. Commun., 2001, 1740
Liu, Y., Feng, X., Zhi, J.G. and Tong, B., Chinese J. Polym. Sci., 2012, 30(3): 443
Li, Z., Dong, Y.Q., Lam, J.W., Sun, J., Qin, A., Häußler, M., Dong, Y.P., Sung, H.H., Williams, I.D. and Kwok, H.S., Adv. Funct. Mater., 2009, 19: 905
Wang, M., Zhang, G., Zhang, D., Zhu, D. and Tang, B.Z., J. Mater. Chem., 2010, 20: 1858
Qi, X., Li, H., Lam, J.W.Y., Yuan, X., Wei, J., Tang, B.Z. and Zhang, H., Adv. Mater., 2012, 24: 4191
Chi, Z., Zhang, X., Xu, B., Zhou, X., Ma, C., Zhang, Y., Liu, S. and Xu, J., Chem. Soc. Rev., 2012, 41: 3878
Zhang, X., Chi, Z., Li, H., Xu, B., Li, X., Zhou, W., Liu, S., Zhang, Y. and Xu, J., Chem. Asian J., 2011, 6: 808
Zhang, X., Chi, Z., Li, H., Xu, B., Li, X., Liu, S., Zhang, Y. and Xu, J., J. Mater. Chem., 2011, 21: 1788
Zhang, X., Chi, Z., Zhang, Y., Liu, S. and Xu, J., J. Mater. Chem. C, 2013, 1: 3376
Zhou, X., Li, H., Chi, Z., Zhang, X., Zhang, J., Xu, B., Zhang, Y., Liu, S. and Xu, J., New J. Chem., 2012, 36: 685
Li, X., Zhang, X., Chi, Z., Chao, X., Zhou, X., Zhang, Y., Liu, S. and Xu, J., Anal. Methods, 2012, 4: 3338
Chi, Z., He, K., Li, H., Zhang, X., Xu, B., Liu, S., Zhang, Y. and Xu, J., Chem. J. Chin. Univ., 2012, 33: 725
An, B.K., Kwon, S.K., Jung, S.D. and Park, S.Y., J. Am. Chem. Soc., 2002, 124: 14410
Zhang, X., Liu, M., Yang, B., Zhang, X., Chi, Z., Liu, S., Xu, J. and Wei, Y., Polym. Chem., 2013, 4: 5060
Zhang, X., Zhang, X., Yang, B., Hui, J., Liu, M., Chi, Z., Liu, S., Xu, J. and Wei, Y., Polym. Chem., 2014, 5: 318
Zhang, X., Yang, Z., Chi, Z., Chen, M., Xu, B., Wang, C., Liu, S., Zhang, Y. and Xu, J., J. Mater. Chem., 2010, 20: 292
Zhang, X., Chi, Z., Xu, B., Li, H., Yang, Z., Li, X., Liu, S., Zhang, Y. and Xu, J., Dyes Pigm., 2011, 89: 56
Zhang, X., Chi, Z., Xu, B., Li, H., Zhou, W., Li, X., Zhang, Y., Liu, S. and Xu, J., J. fluoresc., 2011, 21: 133
Li, X., Chi, Z., Xu, B., Li, H., Zhang, X., Zhou, W., Zhang, Y., Liu, S. and Xu, J., J. fluoresc., 2011, 21: 1969
Chen, C., Liao, J.Y., Chi, Z., Xu, B., Zhang, X., Kuang, D.B., Zhang, Y., Liu, S. and Xu, J., J. Mater. Chem., 2012, 22: 8994
Yang, Z., Yu, T., Chen, M., Zhang, X., Wang, C., Xu, B., Zhou, X., Liu, S., Zhang, Y., Chi, Z. and Xu, J., Acta Polymerica Sinica (in Chinese), 2009, (6): 560
Wang, Z., Xu, B., Zhang, L., Zhang, J., Ma, T., Zhang, J., Fu, X. and Tian, W., Nanoscale, 2013, 5: 2065
He, J., Xu, B., Chen, F., Xia, H., Li, K., Ye, L. and Tian, W., J. Phys. Chem. C, 2009, 113: 9892
Zhang, X., Chi, Z., Zhang, J., Li, H., Xu, B., Li, X., Liu, S., Zhang, Y. and Xu, J., J. Phys. Chem. B, 2011, 115: 7606
Zhang, X., Chi, Z., Xu, B., Chen, C., Zhou, X., Zhang, Y., Liu, S. and Xu, J., J. Mater. Chem., 2012, 22: 18505
Zhang, X., Chi, Z., Zhou, X., Liu, S., Zhang, Y. and Xu, J., J. Phys. Chem. C, 2012, 116: 23629
Zhang, X., Chi, Z., Xu, B., Jiang, L., Zhou, X., Zhang, Y., Liu, S. and Xu, J., Chem. Commun., 2012, 48: 10895
Ding, D., Li, K., Qin, W., Zhan, R., Hu, Y., Liu, J., Tang, B.Z. and Liu, B., Adv. Healthc. Mater., 2013, 2: 382
Qin, W., Ding, D., Liu, J., Yuan, W.Z., Hu, Y., Liu, B. and Tang, B.Z., Adv. Funct. Mater., 2012, 22: 771
Li, K., Jiang, Y., Ding, D., Zhang, X., Liu, Y., Hua, J., Feng, S.S. and Liu, B., Chem. Commun., 2011, 47: 7323
Zhang, X., Zhang, X., Wang, S., Liu, M., Tao, L. and Wei, Y., Nanoscale, 2013, 5: 147
Zhang, X., Zhang, X., Yang, B., Wang, S., Liu, M., Zhang, Y., Tao, L. and Wei, Y., RSC Adv., 2013, 3: 9633
Zhang, X., Zhang, X., Wang, S., Liu, M., Zhang, Y., Tao, L. and Wei, Y., ACS Appl. Mater. Interfaces, 2013, 5: 1943
Zhang, X., Zhang, X., Yang, B., Liu, M., Liu, W., Chen, Y. and Wei, Y., Polym. Chem., 2013, 4: 4317
Zhang, X., Zhang, X., Yang, B., Liu, M., Liu, W., Chen, Y. and Wei, Y., Polym. Chem., 2014, 5: 399
Zhang, X., Liu, M., Yang, B., Zhang, X. and Wei, Y., Colloids Surf. B Biointerfaces, 2013, 112: 81
Zhang, X., Zhang, X., Yang, B., Zhang, Y., Liu, M., Liu, W., Chen, Y. and Wei, Y., Colloids Surf. B Biointerfaces, 2014, 113: 435
Zhang, X., Zhang, X., Yang, B., Liu, M., Liu, W., Chen, Y. and Wei, Y., Polym. Chem., 2014, 5: 356
Zhang, X., Ma, Z., Liu, M., Zhang, X., Jia, X. and Wei, Y., Tetrahedron, 2013, 69: 10552
Weng, C.J., Jhuo, Y.S., Chang, C.H., Feng, C.F., Peng, C.W., Dai, C.F., Yeh, J.M. and Wei, Y., Soft Matter, 2011, 7: 10313
Zhang, X., Liu, M., Zhang, Y., Yang, B., Ji, Y., Feng, L., Tao, L., Li, S. and Wei, Y., RSC Adv., 2012, 2: 12153
Cai, X., Hao, J., Zhang, X., Yu, B., Ren, J., Luo, C., Li, Q., Huang, Q., Shi, X. and Li, W., Toxicol. Appl. Pharm., 2010, 243: 27
Zhu, Y., Li, W., Li, Q., Li, Y., Li, Y., Zhang, X. and Huang, Q., Carbon, 2009, 47: 1351
Zhu, Y., Zhang, X., Zhu, J., Zhao, Q., Li, Y., Li, W., Fan, C. and Huang, Q., Int. J. Mol. Sci., 2012, 13: 12336
Zhang, X., Wang, S., Liu, M., Hui, J., Yang, B., Tao, L. and Wei, Y., Toxicol. Res., 2013, 2: 335
Zhang, X., Yin, J., Kang, C., Li, J., Zhu, Y., Li, W., Huang, Q. and Zhu, Z., Toxicol. Lett., 2010, 198: 237
Zhang, X., Yin, J., Peng, C., Hu, W., Zhu, Z., Li, W., Fan, C. and Huang, Q., Carbon, 2011, 49: 986
Li, J., Zhu, Y., Li, W., Zhang, X., Peng, Y. and Huang, Q., Biomaterials, 2010, 31: 8410
Yang, B., Zhang, Y., Zhang, X., Tao, L., Li, S. and Wei, Y., Polym. Chem., 2012, 3: 3235
Zhang, Y., Yang, B., Zhang, X., Xu, L., Tao, L., Li, S. and Wei, Y., Chem. Commun., 2012, 48: 9305
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This work was financially supported by the National Natural Science Foundation of China (Nos. 21134004, 21201108 and 51363016), and the National 973 Project (No. 2011CB935700), China Postdoctoral Science Foundation (Nos. 2012M520243, 2013T60100).
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Zhang, Xq., Zhang, Xy., Yang, B. et al. Facile fabrication of aggregation-induced emission based red fluorescent organic nanoparticles for cell imaging. Chin J Polym Sci 32, 871–879 (2014). https://doi.org/10.1007/s10118-014-1461-6
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DOI: https://doi.org/10.1007/s10118-014-1461-6