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Abstract

Chemically tailorable styrylbenzene and phenyleneethynylene derivatives (SBs and PEs) are the subject of intense research, and are relevant in the fields of sensory materials and optoelectronic device engineering. To this end, the focus of this thesis is construction of SBs and PEs and investigating their optical properties and sensing applications. In chapter 2, we focus on the styrylbenzene derivatives. On the basis of tristyrylbenzene (TSB), we take the advantage of aggregation-induced emission (AIE) into account, design two isomers and explore the regioisomerism effect on the optical properties (chapter 2.1). Then, using the 1,3,5-tristyrylbenzene as a star-shaped core, we extend the moleculer skeleton and design a series of tristyrylbenzene derivatives to investigate their photophysical properties and optical response to acid and metal ions. The transition metals such as Al3+, Mn2+, Fe3+, Fe2+, Cd2+, Ag+ and Hg2+ can be well discriminated by these SBs (chapter 2.2). Using ionic phenyleneethynylene derivatives as sensors for analytes with similar structure is interesting. In chapter 3, we focus on the phenyleneethynylene derivatives. We first construct a sensor array composed of three anionic poly(p-phenyleneethynylene)s (PPEs), and their electrostatic complexes with metal ions (Fe2+, Cu2+, Co2+). This array discriminates PTH-amino acid residues degraded from an oligopeptide through Edman sequencing (chapter 3.1). Given that synthesis of guanidine-substituted PEs and their characterization remains a challenge, we design a series of PE-trimers bearing N-Boc-protected guanidine side groups, to address the deprotection defects under regular condition (DCM/TFA). Meanwhile, their optical properties are discussed (chapter 3.2). On the basis of above research, we prepare the true guanidinium-PPE (chapter 3.3) and reveal that this material is a precious sensor for nitroaromatics. The guanidinium-PPE could detect picric acid with high selectivity and sensitivity in water. All together, these results contribute to the development of research on hydrocarbon AIEgens and the application of SB/PE-based materials for luminescent chemosensors.