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Polymer Chemistry Polymer Chemistry View Article Online REVIEW View Journal | View Issue Fluorescent chemosensors based on conjugated polymers with N-heterocyclic moieties: two Cite this: Polym. Chem., 2020, 11, 3095 decades of progress Taisheng Wang,a,b Na Zhang,a,b Wei Baic and Yinyin Bao *d Among various fluorescent chemosensors based on different platforms, π-conjugated polymer-based sensors have attracted much attention, owing to their amplified detection sensitivity in the detection of a variety of environmental pollutants and bioactive compounds. Since the report of the first conjugated polymer sensor in the 90s, this sensing platform has achieved more than two decades of progress, with an explosion of the research in this field observed in the last ten years. In this review, we will focus on flu- orescent polymer sensors with N-heterocyclic aromatic moieties, which have played a pivotal role since Received 1st March 2020, the beginning of the development of the conjugated polymer-based fluorescence sensing strategy. We Accepted 22nd April 2020 will highlight the representative examples according to the different types of heterocycles, illustrate the Creative Commons Attribution 3.0 Unported Licence. DOI: 10.1039/d0py00336k structure–property relationships, point out the limitations and challenges of current systems, and also rsc.li/polymers identify possible future research directions. 1. Introduction Sensors provide a communication interface between humans and the surrounding world. To perceive external signals, aSchool of Materials Science and Engineering, Nanjing Institute of Technology, This article is licensed under a Nanjing, 211167, P. R. China during the long period of evolution, the human body has bJiangsu Key Laboratory of Advanced Structural Materials and Application formed five sets of sensors, that is nose, tongue, eyes, ears, Technology, Nanjing, 211167, P. R. China and skin.1 Inspired by nature, chemists have also been cInstitute of Physical Science and Information Technology, Anhui University, Open Access Article. Published on 24 April 2020. Downloaded 10/5/2021 3:27:30 PM. working on developing synthetic chemical sensors to detect Hefei 230601, China d various analytes due to their significance in biomedical ana- Institute of Pharmaceutical Sciences, Department of Chemistry and Applied 2 Biosciences, ETH Zurich, 8093 Zurich, Switzerland. lysis and environmental protection. Chemical sensors with E-mail: [email protected] fluorescence as the output signal, commonly called fluorescent Taisheng Wang received a BS Na Zhang received a BS degree degree in polymer materials and in polymer materials and engin- engineering from the Hefei eering from the Hefei University University of Technology (2011) of Technology (2013) and a PhD and a PhD in chemistry from the in chemistry from the University University of Science and of Science and Technology of Technology of China (2017). He China (2018). She is currently a is currently a lecturer of the lecturer of the Department of Department of Polymer and Polymer and Composite Composite Engineering at Engineering at Nanjing Institute Nanjing Institute of Technology. of Technology. Her scientific His scientific interests mainly interests mainly focus on the Taisheng Wang concern the preparation of Na Zhang design and synthesis of two- chemically and mechanically dimensional materials and the responsive polymeric materials, and synthesis and characteriz- preparation of chemically and mechanically responsive polymeric ation of self-strengthening polymers. materials. This journal is © The Royal Society of Chemistry 2020 Polym. Chem.,2020,11,3095–3114 | 3095 View Article Online Review Polymer Chemistry chemosensors, have exhibited great advantage compared to cally with distinctly high sensitivity for fluorescence sensing, traditional analytical methods, such as mass spectrometry,3 benefiting from their ability to transport electronic excited Raman spectroscopy4 and ion mobility spectroscopy.5 This is states. According to the theory of Swager and coworkers, who because fluorescence signals can enable high sensitivity and first developed CP-based chemosensors,10a excitons in selectivity, fast measurement, low cost, in situ analysis, and excited states can rapidly migrate throughout the conjugated sometimes even “naked eye” detection. Fluorescent chemo- polymer chain or even diffuse within the bulk solid state. sensors are generally designed based on one system which This is due to both space dipolar couplings and strong consists of two key components: a receptor and a fluorophore. mixing of electronic states; thus the polymer backbone can The receptor can selectively interact with a specific analyte in a be viewed as a molecular wire. When CPs are constructed as a certain way, usually through coordination, ionic interaction, detection system, once an analyte appears and interacts with hydrogen bonding, or chemical reaction, and thereafter the the receptor moiety of the polymer sensor, the excitation elec- fluorophore can change its photophysical properties when the tron/energy transfer from the CP to the analyte will occur interactions between the receptor and analyte occur.6 In par- immediately along the whole polymer backbone. As a conse- ticular, a certain spacer connecting the two components can quence, a greatly amplified signal can be achieved, resulting also be introduced to optimize the sensing performance in in enhanced sensitivity, a unique benefit that conventional some cases.7 molecular sensors do not possess. Moreover, different from Fluorescence sensing usually utilizes one of the following fluorescent chemosensors based on small molecules, the CP- characters: mostly the fluorescence intensity change (“turn- based sensors also display excellent film-forming properties on” or “turn-off”) and spectral shift (emission color change), and high flexibility for chemical design and structure – as well as the fluorescence life time variation and polarization modification.10b e change, to a lesser extent.8 These changes may be triggered Since the report of the first example by Swager and co- by interactions between sensors and analytes of interest. In workers in the 90s,10f the CP-based sensing strategy has Creative Commons Attribution 3.0 Unported Licence. general, the performance of a fluorescent chemosensor is achieved more than two decades of progress, with an explosion usually determined by its selectivity and sensitivity. Other of the research in this field observed in the last ten years.10g,h characteristics including the response time, recovery time, A number of CP-based fluorescent chemosensors have been reversibility, overall lifetime, and cost, are also considered for developed with various polymer backbones and receptor moi- real applications. In addition, like any other analytical tools, eties, and they have exhibited profound potential in biosen- the ease of use, high accuracy, and acceptable reproducibility sing and environmental analysis, including metal ion/anion of the results are also expected from the sensors.9 Among detection, biomolecule sensing, bioimaging, explosive detec- various fluorescent chemosensors from different materials, tion, etc.11 A series of comprehensive review papers have also π-conjugated polymer (CP)-based sensors have attracted been published on this topic;11a,b,f,g however, to our knowl- This article is licensed under a much attention as they can be used to detect a variety of edge, there is still no such review that exclusively focuses on environmental pollutants and bioactive compounds, owing to the nitrogen receptor moiety of the CP sensors, especially for their amplified detection sensitivity. These conjugated poly- the ones based on aromatic N-heterocycles. The conjugated Open Access Article. Published on 24 April 2020. Downloaded 10/5/2021 3:27:30 PM. mers are referred to as amplifying fluorescent polymers, typi- polymers with aromatic N-heterocyclic moieties indeed played Dr Wei Bai has been a Professor Yinyin Bao is a group leader in at the Institute of Physical the Institute of Pharmaceutical Science and Information Science at ETH Zürich. He Technology of Anhui University received his PhD degree in since 2018. He received his PhD Polymer Chemistry from the (2014) from the Department of University of Science and Chemistry of Louisiana State Technology of China (2012). University – Baton Rouge and After completing his postdoctoral worked as a Postdoctoral research at KU Leuven, he Research Associate at the became a Marie Curie University of Massachusetts and IntraEuropean Fellow in CNRS & the University of Tennessee for Univ. Paris Sud. In 2016, he Wei Bai three years before joining the Yinyin Bao joined ETH Zürich, and he was Anhui University. His area of promoted to a Senior Scientist interest focuses on the synthesis of novel polymeric and supramo- position in late 2018. His research interest remains the application lecular materials, especially organic 2D polymers and functional of synthetic molecules and polymers in the biomedical area, such fluorescent molecules. as fluorescence sensing and imaging, drug delivery, 3D printed medical devices, etc. 3096 | Polym. Chem.,2020,11,3095–3114 This journal is © The Royal Society of Chemistry 2020 View Article Online Polymer Chemistry Review a pivotal role during the development process of CP sensors,12 with the first example employing a 2,2′-bipyridyl group reported in 1997 by Wasielewski and coworkers.12c On the occasion of the 100th anniversary of polymer chemistry, we would like to take
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