Synthesis and property of solvatochromic fluorophore based on D-pi-A molecular system: 2-[[3-cyano-4-(N-ethyl-N-(2-hydroxyethyl)amino)styryl]-5,5-dimethylfuran-2(5H)-ylidene]malononitrile dye.
Synthesis and property of solvatochromic fluorophore based on D-pi-A molecular system: 2-[[3-cyano-4-(N-ethyl-N-(2-hydroxyethyl)amino)styryl]-5,5-dimethylfuran-2(5H)-ylidene]malononitrile dye.
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DOI：
10.1016/j.saa.2009.10.015
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发表时间：
2010
期刊：
影响因子：
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通讯作者：
Y. Son;S. Gwon;Sue-Yoen Lee;Sung-Hoon Kim
中科院分区：
文献类型：
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作者：
Y. Son;S. Gwon;Sue-Yoen Lee;Sung-Hoon Kim
以4-[（2-羟基乙基）-甲基-氨基]-苯甲醛（供体段）与2-氰乙基-3-氰-4,5,5-三甲基-2,5-二氢呋喃（受体段）缩合为原料，制备了2-{[3-氰-4-（n-乙基- n-（2-羟乙基）氨基）苯基]-5,5-二甲基呋喃-2(5H)-乙基}丙二腈苯基染料。讨论并确定了相应的分子内电荷转移染料发色团的设计、合成和溶剂致变色特性。在不同极性的溶剂介质中监测了其吸收光谱和荧光发射光谱等光学性质。在此测定中，所制备的染料发色团表现出正的溶剂化变色效应，并通过半经验计算对所得的溶剂化变色特性进行了研究。利用Material Studio 4.3通过计算模拟的方法计算了该染料发色团的能量势，如HOMO和LUMO值。此外，通过分子内电荷转移体系的去质子化/质子化效应，测定了DMSO在碱酸加成的pH刺激下作为分子开关传感器的功能。
2-{[3-Cyano-4-(N-ethyl-N-(2-hydroxyethyl)amino)styryl]-5,5-dimethylfuran-2(5H)-ylidene}malononitrile styryl dye was prepared by the condensation of 4-[(2-hydroxy-ethyl)-methyl-amino]-benzaldehyde (donor moiety) with 2-cyanomethylene-3-cyano-4,5,5-trimethyl-2,5-dihydrofuran (acceptor moiety). The corresponding design, synthesis and solvatochromic characteristics of the intramolecular charge-transfer (ICT) dye chromophore were discussed and determined. Optical properties such as absorption and fluorescence emission spectra were monitored in several solvent media with different polarity. In this determination, the prepared dye chromophore showed positive solvatochromism effect and the resulting solvatochromic characteristics were studied with semiempirical calculations. The energy potentials of this dye chromophore such as HOMO and LUMO values were calculated by computational simulation approaches using Material Studio 4.3. Furthermore, the functions as a molecular switching sensor with pH stimulation of alkali–acid addition were determined in DMSO, which was operated by deprotonation/protonation effects based on intramolecular charge-transfer system.