香豆素单取代蔗糖衍生物的合成及其荧光性能

以7-羟基-4-甲基香豆素为原料制得两个香豆素衍生物(2a和2b);2与蔗糖反应合成了两个新型的香豆素单取代蔗糖衍生物(3a和3b),其结构经1H NMR,IR和LC-MS表征.3a和3b均具有较强的荧光强度,且荧光强度对pH的变化较为敏感,可选择性地识别Fe3+.     

四个香豆素磺酰氯衍生物的合成及其荧光性能的研究

四个香豆素磺酰氯衍生物的合成及其荧光性能的研究曹秋娥,徐其亨（云南大学化学系,昆明,６５００９１）关键词香豆素磺酰氯衍生物,荧光试剂,荧光性能香豆素衍生物是一类较好的荧光试剂,本文以香豆素为母体,合成了４个香豆素磺酰氯衍生物：４－甲基－７－羟基香豆素...     

4-羟基香豆素衍生物的荧光性能

4-羟基香豆素衍生物的荧光性能;水杨酸; 羟基香豆素衍生物; 荧光     

苯并香豆素酯类衍生物的合成及荧光性质研究

以2-羟基-1-萘甲醛为原料,采用改进的Knoevenagel反应合成了苯并香豆素-3-羧酸中间体和4种不同链长的脂肪酯和芳香酯衍生物,采用元素分析和红外光谱对其结构进行了表征.对所有化合物固体粉末的发光性能进行了研究.     

含香豆素荧光基团的富勒烯衍生物的合成及荧光性能研究

通过酯化反应将经醚化修饰过的香豆素与富勒烯相连,得到3种含有香豆素荧光基团的富勒烯衍生物,并用1H NMR、13C NMR、FT-IR、MS进行结构表征。荧光光谱研究发现,与富勒烯连接后的衍生物的荧光强度大大降低,其原因源于富勒烯与激发光的竞争和对香豆素荧光的重吸收。     

具有双光子荧光的新型香豆素类衍生物的合成及其光学性能

以7-碘代香豆素-3-甲酸乙酯为原料通过Sonogashira偶联、酯水解和酰胺化反应合成了新型香豆素类衍生物--7-（4-甲氧基苯乙炔基）香豆素-3-N-炔丙基甲酰胺（4）,其结构经¹H NMR, ¹³C NMR, HR-MS(ESI)和元素分析表征。并对其紫外-可见吸收光谱、荧光发射光谱及双光子荧光光谱进行了研究。结果表明：溶剂极性对4的光学性质影响显著,4具有明显的溶致变色效应。此外,4具有较大的有效双光子吸收截面（在乙酸乙酯、甲苯和氯仿中分别为222.57、 168.98 和211.77 GM）,并可发射较强的双光子诱导荧光。     

双香豆素-3-酰胺衍生物的合成和紫外、荧光性质研究

设计合成了5个新的双香豆素-3-酰胺衍生物,并用IR,NMR,MS和元素分析进行结构表征.用X射线单晶衍射法测定了N,N'-1,3-苯基二-(7-二乙氨基-3-甲酰胺)香豆素(4)的晶体结构,化合物4属于三斜晶系,P-1空间群,晶胞参数a=0.8269(14) nm,b=1.4301(3) nm,c=2.5533(4) nm,α=82.55(4)°,β=86.09(5)°,γ=79.05(1)°,V=2.9367(3) nm3,Dc=1.345 g·cm-3,Z=2,F(000)=1256,μ=0.093 mm-1,最终偏离因子R1=0.0622,wR2=0.1410.研究了它们的紫外和荧光性质,结果表明:紫外吸收光谱均呈双峰结构,化合物最大吸收波长在418～441nm的可见光区域,化合物的荧光发射峰在450～460nm之间;化合物具有高的荧光量子产率,荧光量子产率为0.56～0.65.     

香豆素及其衍生物在二甲基亚砜中的电还原性质

采用循环伏安法对香豆素及其衍生物的电还原进行研究；香豆素的电还原发生在羰基上；如果香豆素衍生物分子上含有吸电子基团，则还原电位正移；如果含有给电子基因，则还原电位负移；如果同时含有吸电子和给电子基因，则表现综合结果。     

含氟香豆素荧光探针的合成及其荧光性能研究

以7-羟基-4-三氟甲基香豆素和1,4,7,10-四氮杂环十二烷(Cyclen)为原料,合成了具有多荧光侧臂的新型香豆素类荧光探针化合物,该合成方法经济简单,且环境友好。关键中间体及目标物经1HNMR、13CNMR和LC-MS分析表征,根据其荧光发射强度的不同讨论了探针化合物在乙腈中的荧光性能。     

Synthesis of some new fused coumarin derivatives

2-Hydrazino-4-hydroxy-5H- [1] -benzopyrano- [ 4,3-d ] -pyrim-idin-5-one (3) was prepared via condensation of 2 with hy-drazine hydrate. Treatment of 3 with methylene chloride, ethyl chloroformate, ethyl chloroacetate and benzaldehyde yielded the corresponding 2 - ( substituted ) hydrazino - 4 -hydro-xy-5H-[1]-benzopyrano-[4, 3-d]-pyrimidin-5-one (4, 5, 6, and 10), followed by cyclization of 4, 5 and 6 with dimethyl fonnamide and fused sodium acetate under reflux, while compound 10 was cyclized with bromine and sodium acetate in acetic acid. Compound 3 reacted with β-(toloyl) acrylic acid, ethyl α-cyano-p-methoxytinnamate, diethyl mal-onate and acetyl chloride affording the corresponding 2-(substituted) hydrazino-4-hydroxy-5H-[1]-benzopyrano-[4, 3-d]-pyrimidin-5-one (12, 13, 14, 15 and 16).     

Effects of coumarin substituents on the photophysical properties of newly synthesised phthalocyanine derivatives

In this study, synthesis of new ligands, 8-hydroxy-3-[p-(3′,4′-dicyanophenoxy)-phenyl]coumarin and 8-hexyloxy-3-[p-(3′,4′-dicyanophenoxy)-phenyl]coumarin, and their phthalocyanines, 2,9,16,23-tetrakis[8-hexyloxy-3-(4-oxyphenyl)coumarin]-metal-free and metallophthalocyanines {M[Pc(OBzCou)₄] (M = 2H, Zn(II), Co(II); Bz: benzene; Cou: coumarin)} were synthesised. The novel chromogenic compounds were characterised by elemental analysis: ¹H NMR, ¹³C NMR, MALDI-TOF, IR and UV–vis spectral data. The effect of coumarin substituents on the photophysical properties of metal-free (H₂Pc) and zinc phthalocyanines (ZnPc) derivatives has been examined. Spectrophotometric measurements revealed that coumarin-substituted ZnPc derivatives were in the unaggregated form, whereas those of H₂Pc species were in aggregated form. It means that substitution of coumarin derivative prevents the cluster formation in the presence of zinc ion in the centre of Pc.     

Photochromic and fluorescence properties of coumarin fulgimides

Four new fulgimides possessing a fluorescent coumarin unit were synthesized from the corresponding fulgides, and their photochromic as well as fluorescence properties were investigated. The open-ring forms of coumarin fulgimides were found to exhibit fluorescence in the visible region. Upon exposure to UV light, the fulgimides were transformed into the nonfluorescent closed-ring forms, which can be reverted to the initial fluorescent open-ring forms on exposure to visible light. The efficiency of quenching of fluorescence was as high as 95% at the photostationary state of UV irradiation.     

Synthesis of new condensed and cyclized coumarin derivatives

Condensation of 4-chloro-2-oxo-2H-chromene-3-carbonitrile with selected heteroarylamines in acetonitrile containing a catalytic amount of triethylamine, followed by intramolecular cyclization, gave the new coumarin derivatives with yields ranging from 43 % to 78 %. The novel compounds were subjected to acid hydrolysis giving the corresponding oxo derivatives in 66–70 % yield. The structural assignments of the synthesized compounds were based on elemental, IR, ¹H and ¹³C NMR analyses.     

Synthesis,characterization, and emulsion polymerization of polymerizable coumarin derivatives

We describe the synthesis of a new polymerizable coumarin derivative, [6‐(β‐acryloxyethoxy)‐7‐isopropoxy‐4‐methyl coumarin ( 3 )], whose UV absorption spectrum significantly overlaps the emission spectrum of 9‐alkyl phenanthrene chromophore. This dye can serve several purposes in latex films. It can be a tracer for fluorescence microscopy experiments, or it can act as a donor or acceptor dye in nonradiative energy transfer experiments. Here we emphasize its role as an energy transfer acceptor in experiments with phenanthrene as the corresponding donor. Coumarin‐labeled poly(butyl methacrylate) latex dispersions could be synthesized by conventional batch emulsion polymerization with complete monomer conversion, complete dye incorporation, and uniform dye distribution. Attempts to extend this reaction to poly(vinyl acetate) copolymers failed because the dye inhibited monomer conversion. © 2004 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 42: 3479–3489, 2004     

N-(取代)-1,3,4-噻二唑基香豆素酰胺类化合物的合成及光谱特性

用6-氯香豆素-3-甲酰氯(Ⅰ)和5-(取代)-2-氨基-1,3,4-噻二唑(Ⅱa-Ⅱi)作用合成了9种新的目标化合物(Ⅲa-Ⅲi),用HRMS,IR和1 H NMR对化合物结构进行了表征,确定了化合物的结构,并对其紫外吸收光谱和荧光光谱进行了分析.研究发现:在紫外光谱中,新化合物(Ⅲa-Ⅲi)和2种原料化合物相比,因共轭链的增长而使其最大吸收波长(λmax)红移;9种化合物表现出比原料化合物(Ⅰ)较强的荧光性能.     

Synthesis,electrochemistry and fluorescence of four new Ru(phen)2/3+ derivatives

Four typical LB monolayer film materials, Ru(phen)2/3 ⁺ complexes with one ligand attached to different long chain alkyl amides, were designed and synthesized. Their chemical structures were identified by the techniques of FT-IR, ¹H NMR and ESI-MS. Also, UV-Vis, electrochemistry and fluorescence of these complexes are reported.     

Synthesis and structure of indoline spiropyrans of the coumarin series

New indoline spiropyrans of the coumarin series were synthesized by the condensation of indoline and hydroxyformylcoumarin derivatives. Spiropyrans, viz., derivatives of 8-formyl-7-hydroxy-4-methylcoumarin and 5-formyl-6-hydroxy-4-methylcoumarin, under irradiation are transformed into open forms, which are recyclized in the dark. The compounds formed by the condensation of the indoline derivatives with 3-formyl-4-hydroxycoumarin have an open structure of the merocyanine dyes and are transformed into spiro forms neither in the dark nor under irradiation with the visible light. Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 10, pp. 2342–2349, October, 2005.     

Synthesis, electrochemistry and fluorescence of four new Ru(phen)_3~(2 ) derivatives

Four typical LB monolayer film materials, Ru(phen)32 complexes with one ligand attached to different long chain alkyl amides, were designed and synthesized. Their chemical structures were identified by the techniques of FT-IR, 1H NMR and ESI-MS. Also, UV-Vis, electrochemistry and fluorescence of these complexes are reported.     

Theoretical study of global and local reactivities of coumarin and its hydroxylated derivatives

Coumarins are bioactive substances of the benzo‐α‐pyrone family, which have shown antioxidant, antiviral, anti‐inflammatory and antitumor activities, among others. 7‐Hydroxycoumarin and 6,7‐dihydroxycoumarin (esculetin) are two coumarin derivatives that have been reported to exhibit antitumor activity, but the action mechanism underlying this activity remains unknown. In this work, to elucidate this mechanism, a theoretical study of the local and global electronic reactivity properties of a series of hydroxylated and dihydroxylated coumarin derivatives with possible antitumor action is performed using Density Functional Theory in aqueous solution. The substitution by one or two hydroxyl groups in the benzene ring of coumarin produces better charge‐donor than charge‐acceptor compounds. All the studied compounds are generally stable in water and exhibit permanent polarization in the solvent. With one hydroxyl substitution, 7‐hydroxycoumarin is the most polar and polarizable derivative, whereas 5,7‐dihydroxycoumarin is the most polar and polarizable compound with two hydroxyl substitutions. 5,7‐Dihydroxycoumarin is suggested to possess antitumor activity. © 2016 Wiley Periodicals, Inc.