卟啉衍生物的合成与液晶行为及催化聚合研究
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摘要
本论文合成了两个系列的新型卟啉衍生物,系统研究了卟啉分子在不同温度下的自组织行为,获得了宽液晶相变温度区间、低结晶温度的室温液晶材料;研究了卟啉与碳纳米管(CNTs)复合物在溶液中的光致电荷转移性质。探索了镍卟啉/MAO体系催化苯乙烯聚合的聚合行为,提出聚合反应机理。本论文的主要创新结果如下:
(1)证实了所合成的两个系列化合物在一定温度下能够自组织形成柱状液晶相,其液晶态稳定性好、相区宽(最宽达252oC)的特点;证明分子间氢键使得大环共轭液晶的清亮点显著升高。
(2)利用共价改性方法,实现了对CNTs的分散;研究了液晶卟啉与CNTs体系的光致电荷转移行为。
(3)系统研究了镍卟啉/MAO体系催化苯乙烯聚合的行为,提出了聚合机理。证明了镍卟啉/MAO体系能够高效引发苯乙烯聚合。
The recent advances in the field of porphyrin derivatives were summarized in the thesis. Porphyrin is a big conjugate annular compound with four nitrogen atoms which may coordinate with metal ions. Porphyrin derivatives have received considerable attention and attracted significant interest for their particular structure and unique physical and chemical properties. They have played an important roll in the field of biological chemistry, medical chemistry, analytical chemistry, catalytic chemistry, material chemistry, etc. Porphyrin derivatives have received considerable attention and attracted significant interest. The review showed the promising applications and the fundamental research trend, especially showed the progress in liquid crystals and catalytic polymerization.
Since the first liquid crystalline porphyrin which shows mesomorphic behavior was synthesized by Goodby in 1980, liquid crystal porphyrins have received considerable attention for their unique photoeletronic property. Synthesized liquid crystal porphyrins have problems of bad stability of mesophase with higher phase transition temperatures and narrower mesophase range. As a result, the application of liquid crystalline porphyrin was restricted. Worthwhile, the periphery of porphyrin and its metal complexes has 12 active positions, which could link up different structures soft side chains. So, we would synthesize new type liquid crystal of porphyrin materials with better stability of mesophase by molecular design. Besides, metalloporphyrin as catalyst for polymerization of epoxides, cyclic carbonate, methacrylonitrile, etc. has been researched widely, but few metalloporphyrin for olefin polymerization has been reported yet. A. Sen reported metalloporphyrin catalyst for olefin polymerization in 2001, and then opened a new area of porphyrin catalyst.
In this thesis, two series of porphyrin derivatives and their metal complexes were synthesized. The proposed molecular structure of the compounds has been confirmed with 1H NMR, elemental analysis, etc. Their mesomorphic behaviors have been researched by DSC, polarized microscopic observation (POM), and X-ray diffraction. Combined with molecular simulation and density studies, the structures of their mesophase were proposed. Besides, the electron transfer between mesomorphic porphyrin and CNTs upon non-covalent method using UV-Vis and fluorescent spectra was studied. Finally, the catalytic property of metal porphyrin was studied. Nickel tetraphenylporphyrin (Ni(II)TPP) was synthesized, and was used in catalytic styrene polymerization using MAO as cocatalyst. The mechanism of the polymerization was discussed and a special coordination mechanism was proposed.
I. The synthesis and characterization of porphyrin derivatives
In this section, two types of liquid crystal porphyrins derivatives, benzoate-substituted porphyrins and benzoylamino-substituted porphyrins, and their metal complexes were synthesized. The proposed molecular structure was confirmed with elemental analyses, UV-Vis, FTIR, and 1H NMR. The two series of novel liquid crystalline porphyrins were summarized below:
(1) Benzoate-substituted porphyrin: meso-tetra[4-(3,4,5-tri-n- alkoxy- benzoate)phenyl]porphyrins (n=7, 12, 16), and its nickel and zinc complexes (n=12);
(2) Benzoylamino-substituted porphyrin: meso-tetra[4-(3,4,5-n-trialkoxy benzoyl amino)phenyl]porphyrins (n=12, 16), and its nickel and zinc complexes (n=12). II. The mesomorphic behaviors of porphyrin derivatives
The mesomorphic behaviors of porphyrin derivatives were researched by DSC, POM, and XRD. Combined with molecular simulation and density studies, their phase structure and molecular packing model was proposed.
All the two series of porphyrin derivatives showed their mesophase under certain temperature and the molecules can self assembled in their mesophase with good stability including wide temperature range and low phase transition temperature. All of the porphyrin derivatives exhibited rectangular columnar phase. Their mesomophic behaviors were greatly dependent on the length of the alkyl chains and their central metal atom. The phase transition temperatures of crystal phase to liquid crystalline (LC) phase(Tm) and LC phase to isotropic phase (Tc) were summarized below: OMR12, Tm=-33 oC, Tc=146.5 oC; AMR12, Tm=-26.0 oC, Tc=225.7 oC; OMR16, Tm=17.5 oC; Tc=109.5 oC; AMR16, Tm=19.3 oC, Tc=189.3 oC; OMR12Zn, Tm=-28.5 oC, Tc=116 oC; AMR12Zn, Tm=-29.9 oC, Tc=203.1 oC; OMR12Ni, Tm=8.6 oC, Tc=136.7; AMR12Ni, Tm=-28.2 oC, Tc=214.3 oC; OMR7, Tm<-50 oC, Tc=169.1 oC.
The Tm of benzoylamino-substituted porphyrin is similar to that of benzoate-substituted porphyrin with the same chain length, but its Tc is rather higher than that of benzoate-substituted porphyrin. Temperature resolved FTIR spectra studies of AMR12 revealed that hydrogen bonding interaction could influence its molecular assemble in its mesomorphic phase, which lead to a more stable mesophase. Finally, liquid crystalline nano-congeries was prepared using precipitation method.
III. Electron transfer behavior of porphyrin/carbon nanotubes system
Electron transfer behavior between mesomorphic porphyrin and carbon nanotubes (CNTs) was studied using UV-Vis and fluorescence spectra, which showed that supramolecular system formed and electron transfer occurred from porphyrin to CNTs, forming electron Donor-Acceptor system, in all conditions including neutral, acid and base solution.
We also developed a simple method to improve nanotube solubility using covalent method. The modified nanotubes displayed good solubility in chloroform, and the electron transfer between porphyrin and modified CNTs was also studied, which revealed they maybe used as energy or electron transfer antennae.
IV. Styrene polymerization catalyzed by Ni(II)TPP/MAO for synthesizing polystyrene
In this section, nickel(II) tetraphenylporphyrin (Ni(II)TPP) was synthesized, and the polymerization of styrene catalyzed with Ni(II)TPP/methylaluminoxane (MAO) was studied. Studies at different polymerization conditions showed that the catalyst system has a high thermal stability and show fairly good activity. The obtained polystyrene was isotactic-rich atactic polymer with narrow molecular weight distribution (PDI=1.5-1.6).
A special coordination mechanism was proposed using ESR, 13C NMR, etc. With initiation, interaction of Ni(II)TPP and MAO formed the polymerization species, on which styrene monomer can insert through 2,1-fashion. More styrene molecules insert and propagating chains are formed. The propagating chains are terminated mainly throughβ-hydrogen elimination.
(1)证实了所合成的两个系列化合物在一定温度下能够自组织形成柱状液晶相,其液晶态稳定性好、相区宽(最宽达252oC)的特点;证明分子间氢键使得大环共轭液晶的清亮点显著升高。
(2)利用共价改性方法,实现了对CNTs的分散;研究了液晶卟啉与CNTs体系的光致电荷转移行为。
(3)系统研究了镍卟啉/MAO体系催化苯乙烯聚合的行为,提出了聚合机理。证明了镍卟啉/MAO体系能够高效引发苯乙烯聚合。
The recent advances in the field of porphyrin derivatives were summarized in the thesis. Porphyrin is a big conjugate annular compound with four nitrogen atoms which may coordinate with metal ions. Porphyrin derivatives have received considerable attention and attracted significant interest for their particular structure and unique physical and chemical properties. They have played an important roll in the field of biological chemistry, medical chemistry, analytical chemistry, catalytic chemistry, material chemistry, etc. Porphyrin derivatives have received considerable attention and attracted significant interest. The review showed the promising applications and the fundamental research trend, especially showed the progress in liquid crystals and catalytic polymerization.
Since the first liquid crystalline porphyrin which shows mesomorphic behavior was synthesized by Goodby in 1980, liquid crystal porphyrins have received considerable attention for their unique photoeletronic property. Synthesized liquid crystal porphyrins have problems of bad stability of mesophase with higher phase transition temperatures and narrower mesophase range. As a result, the application of liquid crystalline porphyrin was restricted. Worthwhile, the periphery of porphyrin and its metal complexes has 12 active positions, which could link up different structures soft side chains. So, we would synthesize new type liquid crystal of porphyrin materials with better stability of mesophase by molecular design. Besides, metalloporphyrin as catalyst for polymerization of epoxides, cyclic carbonate, methacrylonitrile, etc. has been researched widely, but few metalloporphyrin for olefin polymerization has been reported yet. A. Sen reported metalloporphyrin catalyst for olefin polymerization in 2001, and then opened a new area of porphyrin catalyst.
In this thesis, two series of porphyrin derivatives and their metal complexes were synthesized. The proposed molecular structure of the compounds has been confirmed with 1H NMR, elemental analysis, etc. Their mesomorphic behaviors have been researched by DSC, polarized microscopic observation (POM), and X-ray diffraction. Combined with molecular simulation and density studies, the structures of their mesophase were proposed. Besides, the electron transfer between mesomorphic porphyrin and CNTs upon non-covalent method using UV-Vis and fluorescent spectra was studied. Finally, the catalytic property of metal porphyrin was studied. Nickel tetraphenylporphyrin (Ni(II)TPP) was synthesized, and was used in catalytic styrene polymerization using MAO as cocatalyst. The mechanism of the polymerization was discussed and a special coordination mechanism was proposed.
I. The synthesis and characterization of porphyrin derivatives
In this section, two types of liquid crystal porphyrins derivatives, benzoate-substituted porphyrins and benzoylamino-substituted porphyrins, and their metal complexes were synthesized. The proposed molecular structure was confirmed with elemental analyses, UV-Vis, FTIR, and 1H NMR. The two series of novel liquid crystalline porphyrins were summarized below:
(1) Benzoate-substituted porphyrin: meso-tetra[4-(3,4,5-tri-n- alkoxy- benzoate)phenyl]porphyrins (n=7, 12, 16), and its nickel and zinc complexes (n=12);
(2) Benzoylamino-substituted porphyrin: meso-tetra[4-(3,4,5-n-trialkoxy benzoyl amino)phenyl]porphyrins (n=12, 16), and its nickel and zinc complexes (n=12). II. The mesomorphic behaviors of porphyrin derivatives
The mesomorphic behaviors of porphyrin derivatives were researched by DSC, POM, and XRD. Combined with molecular simulation and density studies, their phase structure and molecular packing model was proposed.
All the two series of porphyrin derivatives showed their mesophase under certain temperature and the molecules can self assembled in their mesophase with good stability including wide temperature range and low phase transition temperature. All of the porphyrin derivatives exhibited rectangular columnar phase. Their mesomophic behaviors were greatly dependent on the length of the alkyl chains and their central metal atom. The phase transition temperatures of crystal phase to liquid crystalline (LC) phase(Tm) and LC phase to isotropic phase (Tc) were summarized below: OMR12, Tm=-33 oC, Tc=146.5 oC; AMR12, Tm=-26.0 oC, Tc=225.7 oC; OMR16, Tm=17.5 oC; Tc=109.5 oC; AMR16, Tm=19.3 oC, Tc=189.3 oC; OMR12Zn, Tm=-28.5 oC, Tc=116 oC; AMR12Zn, Tm=-29.9 oC, Tc=203.1 oC; OMR12Ni, Tm=8.6 oC, Tc=136.7; AMR12Ni, Tm=-28.2 oC, Tc=214.3 oC; OMR7, Tm<-50 oC, Tc=169.1 oC.
The Tm of benzoylamino-substituted porphyrin is similar to that of benzoate-substituted porphyrin with the same chain length, but its Tc is rather higher than that of benzoate-substituted porphyrin. Temperature resolved FTIR spectra studies of AMR12 revealed that hydrogen bonding interaction could influence its molecular assemble in its mesomorphic phase, which lead to a more stable mesophase. Finally, liquid crystalline nano-congeries was prepared using precipitation method.
III. Electron transfer behavior of porphyrin/carbon nanotubes system
Electron transfer behavior between mesomorphic porphyrin and carbon nanotubes (CNTs) was studied using UV-Vis and fluorescence spectra, which showed that supramolecular system formed and electron transfer occurred from porphyrin to CNTs, forming electron Donor-Acceptor system, in all conditions including neutral, acid and base solution.
We also developed a simple method to improve nanotube solubility using covalent method. The modified nanotubes displayed good solubility in chloroform, and the electron transfer between porphyrin and modified CNTs was also studied, which revealed they maybe used as energy or electron transfer antennae.
IV. Styrene polymerization catalyzed by Ni(II)TPP/MAO for synthesizing polystyrene
In this section, nickel(II) tetraphenylporphyrin (Ni(II)TPP) was synthesized, and the polymerization of styrene catalyzed with Ni(II)TPP/methylaluminoxane (MAO) was studied. Studies at different polymerization conditions showed that the catalyst system has a high thermal stability and show fairly good activity. The obtained polystyrene was isotactic-rich atactic polymer with narrow molecular weight distribution (PDI=1.5-1.6).
A special coordination mechanism was proposed using ESR, 13C NMR, etc. With initiation, interaction of Ni(II)TPP and MAO formed the polymerization species, on which styrene monomer can insert through 2,1-fashion. More styrene molecules insert and propagating chains are formed. The propagating chains are terminated mainly throughβ-hydrogen elimination.
引文
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