Abstract
The photoswitching poly(pyrene-1-ylmethyl-methacrylate-random-methyl methacrylate-random-methacrylate spirooxazine) was synthesized via atom transfer radical polymerization and characterized by proton nuclear magnetic resonance (1H NMR), gel permeation chromatography (GPC), Fourier transform infrared (FTIR) spectroscopy, UV-visible spectroscopy, and differential scanning calorimetry (DSC). The obtained copolymer exhibited the capability of erasable and rewritable photoimaging, making it a potential candidate for optical data storage materials. Moreover, the copolymer also showed the sensing ability for cyanide anions effect in aqueous solutions.
Article PDF
Similar content being viewed by others
Explore related subjects
Discover the latest articles, news and stories from top researchers in related subjects.Avoid common mistakes on your manuscript.
References
O. Emanuele and S. Paolo, Adv. Mater., 26, 1827 (2014).
T. Mizokuro, H. Mochizuki, A. Kobayashi, S. Horiuchi, N. Yamamoto, N. Tanigaki, and T. Hiraga, Chem. Mater., 16, 3469 (2004).
Z. Junji, Z. Qi, and T. He, Adv. Mater., 25, 378 (2013).
E. Fischer and Y. Hirshberg, Royal Soc. Chem., 4522 (1952).
M. Dübner, V. J. Cadarso, T. N. Gevrek, A. Sanyal, N. D. Spencer, and C. Padeste, ACS Appl. Mater. Interfaces, 9, 9245 (2017).
C. Ventura, P. Thornton, S. Giordani, and A. Heise, Polym. Chem., 5, 6318 (2014).
M. R. di Nunzio, P. L. Gentili, A. Romani, and G. Favaro, J. Phys. Chem. C, 114, 6123 (2010).
V. A. Lokshin, A. Samat, and A. V. Metelitsa, Russ. Chem. Rev., 71, 893 (2002).
H. Bouas-Laurent and H. Dürr, Pure Appl. Chem., 73, 639 (2001).
A. J. Myles, T. J. Wigglesworth, and N. R. Branda, Adv. Mater., 15, 745 (2003).
S.-J. Lim, J. Seo, and S. Y. Park, J. Am. Chem. Soc., 128, 14542 (2006).
S.-J. Lim, B.-K. An, and S. Y. Park, Macromolecules, 38, 6236 (2005).
T. Feczkó, O. Varga, M. Kovács, T. Vidóczy, and B. Voncina, J. Photochem. Photobiol. A: Chem., 222, 293 (2011).
W. Shaodong, L. Xinghai, Y. Mei, Z. Yu, X. Keyu, and T. Rong, Packaging Technol. Sci., 28, 839 (2015).
G. Berkovic, V. Krongauz, and V. Weiss, Chem. Rev., 100, 1741 (2000).
J.-S. Lin, Eur. Polym. J., 39, 1693 (2003).
K. Ock, N. Jo, J. Kim, S. Kim, and K. Koh, Synth. Met., 117, 131 (2001).
P. J. Castro, I. Gómez, M. Cossi, and M. Reguero, J. Phys. Chem. A, 116, 8148 (2012).
T. Suzuki, F.-T. Lin, S. Priyadashy, and S. G. Weber, Chem. Commun., 2685 (1998).
M. Tomasulo, S. Sortino, A. J. P. White, and F. M. Raymo, J. Org. Chem., 70, 8180 (2005).
X. Meng, W. Zhu, Z. Guo, J. Wang, and H. Tian, Tetrahedron, 62, 9840 (2006).
S.-H. Kim, C.-H. Ahn, S.-R. Keum, and K. Koh, Dyes Pigm., 65, 179 (2005).
M. M. Paquette, B. O. Patrick, and N. L. Frank, J. Am. Chem. Soc., 133, 10081 (2011).
M. Tanaka, K. Kamada, H. Ando, T. Kitagaki, Y. Shibutani, S. Yajima, H. Sakamoto, and K. Kimura, Chem. Commun., 1453 (1999).
J. T. C. Wojtyk, E. Buncel, and P. M. Kazmaier, Chem. Commun., 1703 (1998).
M. Tanaka, M. Nakamura, M. A. A. Salhin, T. Ikeda, K. Kamada, H. Ando, Y. Shibutani, and K. Kimura, J. Org. Chem., 66, 1533 (2001).
Y.-Y. Shi, L. Wu, J. Gao, and M. Shi, J. Macromol. Sci., Part A, 54, 853 (2017).
M. Beija, M.-T. Charreyre, and J. M. G. Martinho, Prog. Polym. Sci., 36, 568 (2011).
S. Yitzchaik, J. Ratner, F. Buchholtz, and V. Krongauz, Liq. Cryst., 8, 677 (1990).
X. Li, C. Li, S. Wang, H. Dong, X. Ma, and D. Cao, Dyes Pigm., 142, 481 (2017).
F. Krohm, J. Kind, R. Savka, J. Alcaraz, D. Herold, H. Plenio, C. M. Thiele, and A. Andrieu-Brunsen, J. Mater. Chem. C, 4, 4067 (2016).
G. K. Such, R. A. Evans, and T. P. Davis, Mol. Cryst. Liq. Cryst., 430, 273 (2005).
G. K. Such, R. A. Evans, and T. P. Davis, Macromolecules, 39, 1391 (2006).
G. K. Such, R. A. Evans, and T. P. Davis, Macromolecules, 37, 9664 (2004).
D. S. Achilleos and M. Vamvakaki, Macromolecules, 43, 7073 (2010).
S. Chen, H. Liu, H. Cui, J. Hu, and H. Cai, Des. Monomers Polym., 18, 574 (2015).
H. T. Nguyen, L.-T. T. Nguyen, and T. V. Le, Des. Monomers Polym., 18, 271 (2015).
Y. Shiraishi, K. Adachi, M. Itoh, and T. Hirai, Org. Lett., 11, 3482 (2009).
S. Zhu, M. Li, L. Sheng, P. Chen, Y. Zhang, and S. X.-A. Zhang, Analyst, 137, 5581 (2012).
I. S. Park, Y.-S. Jung, K.-J. Lee, and J.-M. Kim, Chem. Commun., 46, 2859 (2010).
K. Prakash, P. Ranjan Sahoo, and S. Kumar, Sens. Actuators B, 237, 856 (2016).
Y. Shiraishi, S. Sumiya, K. Manabe, and T. Hirai, ACS Appl. Mater. Interfaces, 3, 4649 (2011).
G. Lin, H. Ding, D. Yuan, B. Wang, and C. Wang, J. Am. Chem. Soc., 138, 3302 (2016).
J. Chao, H. Wang, Y. Zhang, C. Yin, F. Huo, J. Sun, and M. Zhao, New J. Chem., 42, 3322 (2018).
M. Shyamal, P. Mazumdar, S. Maity, G. P. Sahoo, G. Salgado-Morán, and A. Misra, J. Phys. Chem. A, 120, 210 (2016).
A. Senthamizhan, A. Celebioglu, S. Bayir, M. Gorur, E. Doganci, F. Yilmaz, and T. Uyar, ACS Appl. Mater. Interfaces, 7, 21038 (2015).
B. K. Rani and S. A. John, Biosens. Bioelectron., 83, 237 (2016).
T. H. Nguyen, L.-T. T. Nguyen, V. Q. Nguyen, L. Ngoc Tan Phan, G. Zhang, T. Yokozawa, D. Thuy Thi Phung, and H. Tran Nguyen, Polym. Chem., 9, 2484 (2018).
J. Berthet, S. Delbaere, L. M. Carvalho, G. Vermeersch, and P. J. Coelho, Tetrahedron Lett., 47, 4903 (2006).
J. You, J. A. Yoon, J. Kim, C.-F. Huang, K. Matyjaszewski, and E. Kim, Chem. Mater., 22, 4426 (2010).
Author information
Authors and Affiliations
Corresponding author
Additional information
Acknowledgments: This research was fully supported by the Vietnam National Foundation for Science and Technology Development (NAFOSTED) under grant number “104.02-2016.56”.
Electronic supplementary material
Rights and permissions
About this article
Cite this article
Tran, H.M., Nguyen, T.H., Nguyen, V.Q. et al. Synthesis of a Novel Fluorescent Cyanide Chemosensor Based on Photoswitching Poly(pyrene-1-ylmethyl-methacrylate-random-methyl methacrylate-random-methacrylate spirooxazine). Macromol. Res. 27, 25–32 (2019). https://doi.org/10.1007/s13233-019-7030-7
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s13233-019-7030-7