香豆素酮荧光化合物的合成及性质研究
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摘要
香豆素酮化合物具有摩尔消光系数大、荧光量子产率高、稳定性好、最大吸收波长可调谐范围大、易于合成等特点，是一类重要的功能性材料。在荧光染料、太阳能电池光敏剂、有机双光子吸收材料和非线性光学材料等领域具有潜在的应用价值。本文首先参照文献合成了9种3-乙酰基香豆素化合物，在此基础上合成了11种新型的D-π-A型香豆素酮化合物和5种A-π-D型香豆素酮化合物，对合成的全部化合物进行了IR、~1H NMR和MS的表征，同时利用X射线单晶衍射对3-乙酰基-8-甲氧基香豆素分子的晶体结构和空间堆积方式进行了解析。
对以上香豆素化合物结构与光学性能关系的研究表明，香豆素酮化合物较相应的3-乙酰基香豆素化合物的最大吸收峰由299~434nm红移至332~502nm，荧光量子产率由0.032~0.086提高到0.55~0.95。此外，在香豆素环7-位引入供电性基团较4(或6,8)-位对香豆素化合物的光谱性质具有更大的影响，使最大吸收和发射波长红移程度最大，荧光量子产率明显提高。同时具有敏化剂结构的7-二乙氨基-3-[3-(4-氰基乙烯酸苯基)-2-乙烯酰基]香豆素(3b)在可见光区(400~600nm)范围内具有很强的吸收。电化学测试表明该化合物的基态和激发态氧化还原电位均满足作为DSSC中光敏染料的要求，制备的染料敏化太阳能电池的光电转换效率为1.79%，相同条件下，N719标准染料的光电转换效率为6.05%。
运用密度泛函理论(DFT)和含时密度泛函理论(TD-DFT)对以上3类香豆素化合物的几何构型、轨道布局、红外吸收光谱、核磁共振氢谱和紫外-可见吸收光谱进行了理论计算，计算结果与实验值有着很好的一致性。分子轨道布局分析表明，其吸收光谱是源于HOMO→LUMO型的π→π*电子跃迁，即分子在光激发后发生有效的分子内电子转移。计算结果证明了所有香豆素化合物分子结构设计的合理性。
As an important functional material, ketocoumarin compounds afford large molarextinction coefficient, high fluorescence quantum yield, good stability, wide tunablerange of maximum absorptions as well as easy synthesis. These compounds haveexhibited promising potential in many fields such as fluorescent dyes, solar cells,photosensitive agents, organic two-photon absorbing materials and nonlinear opticalmaterials. In this project, eleven novel D-π-A type and five A-π-D type ketocoumarincompounds were synthesized and characterized using FT-IR,~1H NMR and MS. Thestructure of3-acetyl-8-methoxy coumarin was further confirmed by X-ray singlecrystal diffraction.
The relationship between the structures of the novel coumarin and their opticalproperties were studied to show that the corresponding maximum absorption of3-acetyl-coumarin compounds shift from299~434nm to332~502nm. Meanwhile,due to the enhanced conjugacy effect and aryl vinyl ketone structure unit, thefluorescence quantum yield was improved from0.032~0.086to0.55~0.95. Theintroduction of electron-donor group at7-position brings greater impact on thespectral properties of coumarin compounds than at4(or6,8)-positions, resulting inhighest red shift of the maximum absorption and emission wavelength, as well assignificant enhancement of fluorescence quantum yield. The ketocoumarin compound3b bearing sensitizer structure exhibits strong absorption in visible region (400to600nm) and the electrochemical study verified that its redox potential at ground andexcited state can meet the requirements for photosensitive dyes in DSSC. Thephotoelectric conversion efficiency of the DSSC with3b as the sensitive dye wasfound to be1.79%.
Density Functional Theory (DFT) and Time Dependent-Density FunctionalTheory (TD-DFT) were employed to theoretically calculate the geometricconfiguration, track layout, infrared spectroscopy,1H NMR and UV-visible absorptionspectra of the as-synthesized coumarin compounds. The calculation data were foundto be consistent with the experimental results. Furthermore, the study of molecularorbital layout demonstrates that their absorption spectrum originates from π→π* electronic transition from HOMO to LUMO type, that is effective intramolecularelectron transfer after the photoexcitation. The calculation results verify the rationalityof the structure design of all the synthesized coumarin compounds.
对以上香豆素化合物结构与光学性能关系的研究表明，香豆素酮化合物较相应的3-乙酰基香豆素化合物的最大吸收峰由299~434nm红移至332~502nm，荧光量子产率由0.032~0.086提高到0.55~0.95。此外，在香豆素环7-位引入供电性基团较4(或6,8)-位对香豆素化合物的光谱性质具有更大的影响，使最大吸收和发射波长红移程度最大，荧光量子产率明显提高。同时具有敏化剂结构的7-二乙氨基-3-[3-(4-氰基乙烯酸苯基)-2-乙烯酰基]香豆素(3b)在可见光区(400~600nm)范围内具有很强的吸收。电化学测试表明该化合物的基态和激发态氧化还原电位均满足作为DSSC中光敏染料的要求，制备的染料敏化太阳能电池的光电转换效率为1.79%，相同条件下，N719标准染料的光电转换效率为6.05%。
运用密度泛函理论(DFT)和含时密度泛函理论(TD-DFT)对以上3类香豆素化合物的几何构型、轨道布局、红外吸收光谱、核磁共振氢谱和紫外-可见吸收光谱进行了理论计算，计算结果与实验值有着很好的一致性。分子轨道布局分析表明，其吸收光谱是源于HOMO→LUMO型的π→π*电子跃迁，即分子在光激发后发生有效的分子内电子转移。计算结果证明了所有香豆素化合物分子结构设计的合理性。
As an important functional material, ketocoumarin compounds afford large molarextinction coefficient, high fluorescence quantum yield, good stability, wide tunablerange of maximum absorptions as well as easy synthesis. These compounds haveexhibited promising potential in many fields such as fluorescent dyes, solar cells,photosensitive agents, organic two-photon absorbing materials and nonlinear opticalmaterials. In this project, eleven novel D-π-A type and five A-π-D type ketocoumarincompounds were synthesized and characterized using FT-IR,~1H NMR and MS. Thestructure of3-acetyl-8-methoxy coumarin was further confirmed by X-ray singlecrystal diffraction.
The relationship between the structures of the novel coumarin and their opticalproperties were studied to show that the corresponding maximum absorption of3-acetyl-coumarin compounds shift from299~434nm to332~502nm. Meanwhile,due to the enhanced conjugacy effect and aryl vinyl ketone structure unit, thefluorescence quantum yield was improved from0.032~0.086to0.55~0.95. Theintroduction of electron-donor group at7-position brings greater impact on thespectral properties of coumarin compounds than at4(or6,8)-positions, resulting inhighest red shift of the maximum absorption and emission wavelength, as well assignificant enhancement of fluorescence quantum yield. The ketocoumarin compound3b bearing sensitizer structure exhibits strong absorption in visible region (400to600nm) and the electrochemical study verified that its redox potential at ground andexcited state can meet the requirements for photosensitive dyes in DSSC. Thephotoelectric conversion efficiency of the DSSC with3b as the sensitive dye wasfound to be1.79%.
Density Functional Theory (DFT) and Time Dependent-Density FunctionalTheory (TD-DFT) were employed to theoretically calculate the geometricconfiguration, track layout, infrared spectroscopy,1H NMR and UV-visible absorptionspectra of the as-synthesized coumarin compounds. The calculation data were foundto be consistent with the experimental results. Furthermore, the study of molecularorbital layout demonstrates that their absorption spectrum originates from π→π* electronic transition from HOMO to LUMO type, that is effective intramolecularelectron transfer after the photoexcitation. The calculation results verify the rationalityof the structure design of all the synthesized coumarin compounds.
引文
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