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pH 민감성 스티릴 퀴놀리니움 유도체들의 선형 및 비선형 광학 특성의 스위칭에 관한 연구

A study on the pH-triggered Linear and Nonlinear Optical Switches Based on Styryl Quinolinium Derivatives

초록/요약

We report on a series of π-conjugated styryl quinolinium push-pull chromophores and investigate their pH-triggered linear and nonlinear optical properties. Two pH-sensitive functional groups are located at electron acceptor and electron donor, respectively. New styryl quinolinium derivatives with protonated quinolinium group (NHQ) at electron acceptor have dimethylamino, methoxyphenol and phenol group acting as an electron donor for 2-(4-(dimethylamino)styryl)quinolinium 4-methylbenzenesulfonate (DA-NHQ), 2-(4-hydroxy-3-methoxystyryl)quinolinium 4-methylbenzenesulfonate (HM-NHQ), 2-(4-hydroxystyryl)quinolinium 4-methylbenzenesulfonate (OH-NHQ), respectively. These derivatives exist in three different chemical forms that can be interconverted using changes in pH values. We characterize their optical properties by absorption, fluorescence and hyper-Rayleigh scattering measurements in various pH values. Results show that styryl quinolinium derivatives exhibit three states switching mode of fluorescent (FL) and nonlinear optical (NLO) response with high contrast. Interestingly, these derivatives display different FL/NLO switching modes, and therefore have a high potential for imaging applications.

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목차

Ι. Introduction 1
II. Experiments 2
II.1 Chemical structures 2
II.2 Synthesis 4
II.2.1 Materials 4
II.2.2 Synthesis of Intermediate 5
II.2.3 Synthesis of Chromophores 6
II.3 General Characterization 8
II.3.1 1H-NMR Analysis 8
II.3.1.1 1H-NMR Analysis of Intermediate 8
II.3.1.2 1H-NMR Analysis of Chromophores 10
II.3.2 Absorption, Fluorescence Measurements in Various pH Values 13
II.3.3 Determination of pKa Values 14
II.3.3.1 Determination of pKa Values of Intermediate 15
II.3.3.2 Determination of pKa Values of Chromophores 17
II.3.4 Fluorescence Quantum Yield Measurement 18
II.3.4.1 Fluorescence Quantum Yield Measurement of Chromophores 18
III. Results and Discussion 20
III.1 Thermal Analysis 20
III.2 Optical Properties 22
III.2.1 UV-vis Absorption Spectra 22
III.2.2 Fluorescence Spectra 27
III.2.3 Hyper-Rayleigh Scattering Measurement 31
IV. Conclusions 34
V. References 35

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