Abstract
Thermoresponsive fluorescent polymers (TFPs) with unique temperature-dependent luminescent properties are of great importance for the development of new functional devices in recent years. Herein, we facilely synthesized an efficient blue-emissive polymer, abbreviated as PCB-TPE, using tetraphenylethene (TPE) as the main building block. PCB-TPE is thermally stable with a novel property of aggregation induced emission (AIE). The thermoresponsive property and mechanism of PCB-TPE were investigated. Its emission shows temperature-dependent features and reveals fine details in the thermal transitions from −10 °C to 60 °C. The polymer offers a platform for the development of efficient luminescent materials for further biological and optoelectronic applications.
Similar content being viewed by others
References
Mei, J.; Huang, Y. H.; He, T. Progress and trends in AIE–based bioprobes: A brief overview. ACS Appl. Mater. Interfaces 2018,10,12217–12261.
Yang, J.; Huang, J.; Li, Q.; Li, Z. Blue AIEgens: Approaches to control the intramolecular conjugation and the optimized performance of OLED devices. J. Mater. Chem. C 2016, 4, 2663–2684.
Li, Q.; Li, Z. The strong light–emission materials in the aggregated state: What happens from a single molecule to the collective group. Adv. Sci. 2017, 4, 1600484.
Wu, Y. W.; Qin, A. J.; Tang, B. Z. AIE–active polymers for explosive detection. Chinese J. Polym. Sci. 2017, 35, 141–154.
Seeboth, A.; Lötzsch, D.; Ruhmann, R.; Muehling, O. Thermochromic polymers—Function by design. Chem. Rev. 2014, 114, 3037–3068.
Wang, D. P.; Miyamato, R.; Shiraishi, Y.; Hirai, T. BODIPY-conjugated thermoresponsive copolymer as a fluorescent thermometer based on polymer microviscosity. Langmuir 2009, 25, 13176–13182.
Yan, Q.; Yuan, J. Y.; Yuan, W. Z.; Zhou, M.; Yin, Y. W.; Pan, C. Y. Copolymer logical switches adjusted through core–shell micelles: From temperature response to fluorescence response. Chem. Commun. 2008, 46, 6188–6190.
Shiraishi, Y.; Miyamoto, R.; Hirai, T. A hemicyanine–conjugated copolymer as a highly sensitive fluorescent thermometer. Langmuir 2008, 24, 4273–4279.
Gota, C.; Okabe, K.; Funatsu, T.; Harada, Y.; Uchiyama, S. Hydrophilic fluorescent nanogel thermometer for intracellular thermometry. J. Am. Chem. Soc. 2009, 131, 2766–2767.
Zhao, L. Y.; Liu, Y. N.; Wang, S. F.; Tao, Y. T.; Wang, F. F.; Zhang, X. W.; Huang, W. Novel hyperbranched polymers as host materials for green thermally activated delayed fluorescence OLEDs. Chinese J. Polym. Sci. 2017, 35, 490–502.
Chen, J. R.; Zhao, J.; Xu, B. J.; Yang, Z. Y.; Liu, S. W.; Xu, J. R.; Zhang, Y.; Wu, Y. C.; Lv, P. Y.; Chi, Z. G. An AEE–active polymer containing tetraphenylethene and 9,10–distyrylanthracene moieties with remarkable mechanochromism. Chinese J. Polym. Sci. 2017, 35, 282–292.
Tang, L.; Jin, J. K.; Qin, A. J.; Yuan, W. Z.; Mao, Y.; Mei, J.; Sun, J. Z.; Tang, B. Z. A fluorescent thermometer operating in aggregation–induced emission mechanism: Probing thermal transitions of PNIPAM in water. Chem. Commun. 2009, 33, 4974–4976.
Guo, Y.; Yu, X.; Xue, W.; Huang, S.; Dong, J.; Wei, L.; Maroncelli, M.; Li, H. Synthesis, structures, and properties of a fluoranthene–based biphenol polymer as a fluorescent nanothermometer. Chem. Eng. J. 2014, 240, 319–330.
Kim, S.; Torkelson, J. M. Distribution of glass transition temperatures in free–standing, nanoconfined polystyrene films: A test of de Gennes’ sliding motion mechanism. Macromolecules 2011, 44, 4546–4553.
Pietsch, C.; Vollrath, A.; Hoogenboom, R.; Schubert, U. S. A fluorescent thermometer based on a pyrene–labeled thermoresponsive polymer. Sensors 2010, 10, 7979–7990.
Wang, Z.; Chen, S.; Lam, J. W. Y.; Qin, W.; Kwok, R. T. K.; Xie, N.; Hu, Q. L.; Tang, B. Z. Long–term fluorescent cellular tracing by the aggregates of AIE bioconjugates. J. Am. Chem. Soc. 2013, 135, 8238–8245.
Hu, R.; Kang, Y.; Tang, B. Z. Recent advances in AIE polymers. Polymer J. 2016, 48, 359–370.
Zhao, W.; Li, C.; Liu, B.; Wang, X.; Li, P.; Wang, Y.; Wu, C.; Yao, C.; Tang, T.; Liu, X. A new strategy to access polymers with aggregation–induced emission characteristics. Macromolecules 2014, 47, 5586–5594.
Mei, J.; Leung, N. L.; Kwok, R. T.; Lam, J. W.; Tang, B. Z. Aggregation–induced emission: Together we shine, united we soar! Chem. Rv. 2015,115,11718–11940.
Huang, M.; Hsu, C. H.; Wang, J.; Mei, S.; Dong, X.; Li, M.; Liu, H.; Zhang, W.; Aida, T.; Zhang, W. B.; Yue, K.; Cheng, S. Z. D. Selective assemblies of giant tetrahedra via precisely controlled positional interactions. Science 2015, 348, 424–428.
Bao, S. P.; Wu, Q. H.; Qin, W.; Yu, Q. L.; Wang, J.; Liang, G. D.; Tang, B. Z. Sensitive and reliable detection of glass transition of polymers by fluorescent probes based on AIE luminogens. Polym. Chem. 2015, 6, 3537–3542.
Mindemark, J.; Bowden, T. Synthesis and polymerization of alkyl halide–functional cyclic carbonates. Polymer 2011, 52, 5716–5722.
Liang, G. D.; Ren, F.; Gao, H. Y.; Wu, Q.; Zhu, F. M.; Tang, B. Z. Continuously–tunable fluorescent polypeptides through polymer–assisted assembly strategy. Polym. Chem. 2016, 7, 5181.
Wei, W.; Feng, S.; Zheng, C. X.; Liang, G. D.; Gao, H. Y.; Wu, Q.; Zhu, F. M. Glass transition and quantum yield for fluorescent labelled polystyrene core–forming block in self–assembled nanomicelles of amphiphilic diblock copolymers. J. Polym. Res. 2015, 22, 212.
Sasaki, T. Melting of poly(e–caprolactone) studied by step–heating calorimetry. J. Therm. Anal. Calorim. 2013, 111, 717–724.
Liu, C. L.; Lin, M. C.; Chen, H. L.; Műller, A. J. Evolution of crystal orientation in one–dimensionally confined space templated by lamellae–forming block copolymers. Macromolecules 2015, 48, 4451–4460.
He, W. N.; Zhou, B.; Xu, J. T.; Du, B. Y.; Fan, Z. Q. Two growth modes of semicrystalline cylindrical poly(e–caprolactone)–è–poly(ethylene oxide) micelles. Macromolecules 2012, 45, 9768–9778.
He, W. N.; Xu, J. T. Crystallization assisted self–assembly of semicrystalline block copolymers. Prog. Polym. Sci. 2012, 37, 1350–1400.
Acknowledgments
This work was financially supported by the National Natural Science Foundation of China (No. 21374136), the Fundamental Research Funds for the Central Universities (Nos. 17lgjc03 and 18lgpy04), and the Opening Project of the Key Laboratory of Polymer Processing Engineering (South China University of Technology, Ministry of Education, No. KFKT1703).
Author information
Authors and Affiliations
Corresponding authors
Rights and permissions
About this article
Cite this article
Wu, JL., Zhang, C., Qin, W. et al. Thermoresponsive Fluorescent Semicrystalline Polymers Decorated with Aggregation Induced Emission Luminogens. Chin J Polym Sci 37, 394–400 (2019). https://doi.org/10.1007/s10118-019-2201-8
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10118-019-2201-8