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Fluorescent substituted maleimides : from small molecule fluorophore to polymeric barcoding
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Xie, Yujie (2020) Fluorescent substituted maleimides : from small molecule fluorophore to polymeric barcoding. PhD thesis, University of Warwick.
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Official URL: http://webcat.warwick.ac.uk/record=b3717730
Abstract
This thesis explored the synthesis and the fluorescence properties of the substituted maleimides and investigated their applications in polymer and bio related applications.
Chapter 1: A general introduction is given in terms of the basic mechanism in the fluorescent involved photo-physical process. The design strategies of fluorescent materials were described and exampled. The polymer-based fluorescent materials were further highlighted with diverse applications in imaging, labeling, information storage, and many other areas.
Chapter 2: Substituted maleimides as the new class of small molecule fluorophores have been introduced with ideal functional capacity in polymer modification areas. In this chapter, several mono-substituted maleimides have been designed and synthesized through mono-substitution reactions to explore the effect on fluorescent properties. By systematically tailoring the substituents on the C=C double bond (halogen and electron-donating groups), remarkable fluorescent properties such as tunable emission, high fluorescence quantum yields (up to 64%), and solvafluorochromic properties were achieved. Supported by the computational results, the variation of substitution groups allowed us to explore the fluorescence mechanism related to the electron localization. In this regard, the fluorescent properties of substituted maleimide structures could potentially be predicted and tuned for various applications.
Chapter 3: Building upon chapter 2, further exploring the relationship between the structure of maleimides and their optical properties is essential for a full understanding of the fluorescence mechanism. In this chapter, a series of unsymmetrical di-substituted maleimides bearing multiple groups have been designed and synthesized to explore the effect on fluorescent properties and achieve higher degree of modification within one molecule. Significantly, the optical properties were investigated with remarkable red-shifted emissions (~50 nm) expanded from blue to yellow region and achieved large stocks shifts around 160 nm. More importantly, the different electron localization caused by the two substituents were rationalized based on the DFT simulation results. The unexpected aggregation-induced emission effect in amino thiol maleimides bearing thiophenol groups was discovered for the first time, which lead to an interest in the investigation of the maleimides fluorophores in response to the aggregation states.
Chapter 4: A substituted maleimides based polymeric nanogel system has been developed which exhibited robust lifetime-switching behavior via fluorescence resonance energy transfer to a spiropyran photoswitch. In this nanogel system, the manipulating of the fluorescent lifetime by means of UV/Vis light could be applied in the information encrypting and encoding. The ability to reversibly code using fluorescent lifetime enables us to solve the problems of spectra overlap and difficulty in resolving the signal in previous fluorescence barcoding. Furthermore, we showcase the biological applications in living cell barcoding and achieved subcellular coding by fluorescence lifetime imaging technique.
| Item Type: | Thesis (PhD) | ||||
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| Subjects: | Q Science > QD Chemistry | ||||
| Library of Congress Subject Headings (LCSH): | Imides, Imides -- Optical properties, Fluorescent polymers, Fluorescence, Nanogels, Bar coding | ||||
| Official Date: | 2020 | ||||
| Dates: |
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| Institution: | University of Warwick | ||||
| Theses Department: | Department of Chemistry | ||||
| Thesis Type: | PhD | ||||
| Publication Status: | Unpublished | ||||
| Supervisor(s)/Advisor: | O’Reilly, Rachel, K. | ||||
| Sponsors: | University of Warwick. Chancellor's International Scholarship | ||||
| Format of File: | |||||
| Extent: | xxxvi, 261 leaves : illustrations | ||||
| Language: | eng |
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