酞菁化合物的合成及其非线性光学性质研究
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摘要
在目前人们研究的非线性材料中,酞菁分子具有特殊的碳氮共轭双键组成的18-π共轭电子体系,在光和热作用下具有较高的稳定性,酞菁分子的结构具有多样性、易裁剪性等特点,通过取代反应可衍生出具有不同取代配体的酞菁化合物,几乎可以和元素周期表中所有的金属元素发生配位,显示出良好的非线性光学性质,以酞菁为母体的非线性光学材料的开发和应用范围越来越广泛。
传统酞菁的合成方法需要的合成温度较高、反应时间长,合成条件苛刻,限制了酞菁的应用。本文第三章在传统液相合成酞菁的方法基础上,采用了新的合成方法,使用中间体丙酮肟(N, N-二乙基羟胺),在温和的条件下合成出了具有金属配位的酞菁,简化了实验过程、提高了合成效率,并研究探讨了它们的反应条件及合成机理,并采用红外光谱、紫外光谱、液相质谱、1H核磁共振光谱等多种测试手段对合成出的酞菁进行检测,结果表明,我们所合成的酞菁化合物纯度较高并符合预期的分子结构,为酞菁的应用打下了基础。
本文在实验部分使用Z-扫描技术分别在纳秒和飞秒激光脉冲作用下对酞菁化合物进行了非线性光学性质研究,分别研究了不同的样品浓度和输入光功率对酞菁化合物的非线性光学性质的影响,讨论了产生非线性光学吸收特性的物理机制、酞菁的结构对非线性光学性质的影响。而当飞秒激光脉冲与酞菁分子相互作用时会出现一些新的非线性光学现象,这与长脉冲激光作用产生的物理机制是不同的,酞菁溶液表现出较强的三光子吸收,并且随着溶液浓度的增加其三光子非线性吸收系数和非线性折射率都会增加,而当入射光功率逐渐增大时,其三光子非线性吸收系数基本上成线性变化,更加证实了三光子吸收是引起非线性吸收的主要原因。
在本文所合成的四种酞菁中,苯氧基锌酞菁(Pc2)的非线性光学性能较好,是由于酞菁中引入金属Zn,中心离子会影响酞菁的π-共轭,电荷转移将在能级轨道之间产生新的能级差,酞菁材料的非线性光学性能就会发生改变。当酞菁外围引入取代基时,不管是吸电子基团还是给电子基团其非线性光学性能都比未取代的酞菁优异,这是因为将取代基引入酞菁分子,会影响酞菁体系的电子云密度和π电子共轭程度,从而使酞菁材料的非线性光学性能发生改变。本文从理论上提出了酞菁分子在激光脉冲作用下的有效能级模型,计算模拟了分子内部各能级粒子数随入射光强变化的动力学信息,当纳秒激光脉冲作用于酞菁分子上时,酞菁分子的三重态第一激发态对其非线性吸收起主要作用;而当飞秒激光脉冲作用于酞菁分子上时,酞菁分子的非线性吸收为三光子吸收,其非线性吸收主要由单重态高阶激发态吸收起主要作用。
In the study of nonlinear optical materials, phthalocyanines along with their metal derivatives are macromolecules with large number of delocalized electrons and have outstanding chemical and thermal stability. The macrocyclic structure and chemical reactivity of tetrapyrroles offers architectural flexibility and capability of phthalocyanines to accommodate different metallic ions in their cavity, possessing nonlinear optical properties finding extensive applications.
Traditional method of phthalocyanine synthesis at high temperature, reaction time is long, harsh reaction conditions, limiting the application of phthalocyanine. In Chapter III, we succeeded in synthesising phthalocyanines using a new intermediate of acetoxime(N,N-Diethylhydroxylamine) under a mild reaction condition. The samples were characterized by IR, UV, LC/MS and 1HNMR techniques, and the results showed that the molecular structures of the samples were consistent with our expectations. We simplified the experiment process and also improved the efficiency of the synthesis, the foundation for the application of phthalocyanines.
Using the nanosecond and femtosecond laser, the nonlinear optical properties of phthalocyanines molecules are studied by the Z-scan technique. The effects of solution concentration and input laser power on nonlinear optical properties of phthalocyanines are researched. Physical mechanism of nonlinear absorption and the influence of structure of phthalocyanines on the nonlinear optical properties have been discussed. Since interaction between femtosecond laser pulse and phthalocyanines molecules, a new nonlinear optical phenomenon has been found which physical mechanism is different from that with long laser pulse, phthalocyanine solution showed strong three-photon absorption, and with the increase of concentration of its three-photon nonlinear absorption coefficient and nonlinear refractive index will increase, and when the incident power increases, its three photon absorption coefficient is essentially linear, and more confirmed the three-photon absorption is mainly caused by nonlinear absorption.
The nonlinear optical properties of phenoxy-phthalocyanine-Zn (Pc2) of the best, is due to the introduction of the metal Zn, the central ion will affect the phthalocyanineπ-conjugated, charge-transfer orbit in the level energy difference, nonlinear optical properties of phthalocyanine will change. When peripheral phthalocyanine substituent introduced, whether electron withdrawing group or electron donating group than the nonlinear optical properties of substituted phthalocyanine is not excellent, because the introduction of the substituted phthalocyanine molecules, will affect the phthalocyanine system, the electron density and the degree ofπelectron conjugation, so that the phthalocyanine nonlinear optical properties of materials change.
An efficient energy-level model for the phthalocyanines molecules excited by laser pulse is developed, and the intensity dependence of level populations is obtained. When nanosecond pulses input, the absorption is mainly introduced by the first excited state of Triplet state, when femtosecond pulses input, the absorption is mainly introduced by the high excited state of singlet state.
传统酞菁的合成方法需要的合成温度较高、反应时间长,合成条件苛刻,限制了酞菁的应用。本文第三章在传统液相合成酞菁的方法基础上,采用了新的合成方法,使用中间体丙酮肟(N, N-二乙基羟胺),在温和的条件下合成出了具有金属配位的酞菁,简化了实验过程、提高了合成效率,并研究探讨了它们的反应条件及合成机理,并采用红外光谱、紫外光谱、液相质谱、1H核磁共振光谱等多种测试手段对合成出的酞菁进行检测,结果表明,我们所合成的酞菁化合物纯度较高并符合预期的分子结构,为酞菁的应用打下了基础。
本文在实验部分使用Z-扫描技术分别在纳秒和飞秒激光脉冲作用下对酞菁化合物进行了非线性光学性质研究,分别研究了不同的样品浓度和输入光功率对酞菁化合物的非线性光学性质的影响,讨论了产生非线性光学吸收特性的物理机制、酞菁的结构对非线性光学性质的影响。而当飞秒激光脉冲与酞菁分子相互作用时会出现一些新的非线性光学现象,这与长脉冲激光作用产生的物理机制是不同的,酞菁溶液表现出较强的三光子吸收,并且随着溶液浓度的增加其三光子非线性吸收系数和非线性折射率都会增加,而当入射光功率逐渐增大时,其三光子非线性吸收系数基本上成线性变化,更加证实了三光子吸收是引起非线性吸收的主要原因。
在本文所合成的四种酞菁中,苯氧基锌酞菁(Pc2)的非线性光学性能较好,是由于酞菁中引入金属Zn,中心离子会影响酞菁的π-共轭,电荷转移将在能级轨道之间产生新的能级差,酞菁材料的非线性光学性能就会发生改变。当酞菁外围引入取代基时,不管是吸电子基团还是给电子基团其非线性光学性能都比未取代的酞菁优异,这是因为将取代基引入酞菁分子,会影响酞菁体系的电子云密度和π电子共轭程度,从而使酞菁材料的非线性光学性能发生改变。本文从理论上提出了酞菁分子在激光脉冲作用下的有效能级模型,计算模拟了分子内部各能级粒子数随入射光强变化的动力学信息,当纳秒激光脉冲作用于酞菁分子上时,酞菁分子的三重态第一激发态对其非线性吸收起主要作用;而当飞秒激光脉冲作用于酞菁分子上时,酞菁分子的非线性吸收为三光子吸收,其非线性吸收主要由单重态高阶激发态吸收起主要作用。
In the study of nonlinear optical materials, phthalocyanines along with their metal derivatives are macromolecules with large number of delocalized electrons and have outstanding chemical and thermal stability. The macrocyclic structure and chemical reactivity of tetrapyrroles offers architectural flexibility and capability of phthalocyanines to accommodate different metallic ions in their cavity, possessing nonlinear optical properties finding extensive applications.
Traditional method of phthalocyanine synthesis at high temperature, reaction time is long, harsh reaction conditions, limiting the application of phthalocyanine. In Chapter III, we succeeded in synthesising phthalocyanines using a new intermediate of acetoxime(N,N-Diethylhydroxylamine) under a mild reaction condition. The samples were characterized by IR, UV, LC/MS and 1HNMR techniques, and the results showed that the molecular structures of the samples were consistent with our expectations. We simplified the experiment process and also improved the efficiency of the synthesis, the foundation for the application of phthalocyanines.
Using the nanosecond and femtosecond laser, the nonlinear optical properties of phthalocyanines molecules are studied by the Z-scan technique. The effects of solution concentration and input laser power on nonlinear optical properties of phthalocyanines are researched. Physical mechanism of nonlinear absorption and the influence of structure of phthalocyanines on the nonlinear optical properties have been discussed. Since interaction between femtosecond laser pulse and phthalocyanines molecules, a new nonlinear optical phenomenon has been found which physical mechanism is different from that with long laser pulse, phthalocyanine solution showed strong three-photon absorption, and with the increase of concentration of its three-photon nonlinear absorption coefficient and nonlinear refractive index will increase, and when the incident power increases, its three photon absorption coefficient is essentially linear, and more confirmed the three-photon absorption is mainly caused by nonlinear absorption.
The nonlinear optical properties of phenoxy-phthalocyanine-Zn (Pc2) of the best, is due to the introduction of the metal Zn, the central ion will affect the phthalocyanineπ-conjugated, charge-transfer orbit in the level energy difference, nonlinear optical properties of phthalocyanine will change. When peripheral phthalocyanine substituent introduced, whether electron withdrawing group or electron donating group than the nonlinear optical properties of substituted phthalocyanine is not excellent, because the introduction of the substituted phthalocyanine molecules, will affect the phthalocyanine system, the electron density and the degree ofπelectron conjugation, so that the phthalocyanine nonlinear optical properties of materials change.
An efficient energy-level model for the phthalocyanines molecules excited by laser pulse is developed, and the intensity dependence of level populations is obtained. When nanosecond pulses input, the absorption is mainly introduced by the first excited state of Triplet state, when femtosecond pulses input, the absorption is mainly introduced by the high excited state of singlet state.
引文
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