手性卟啉酞菁的设计、合成、有机聚集及非线性光学性质研究
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摘要
卟啉、酞菁化合物作为新型的功能材料,在分子电子学、分子信息存储、非线性光学及材料科学等领域拥有广阔的应用前景,另一方面该类配合物具有易修饰等特点,因此作为有序超分子聚集体的构筑模块得到了人们的高度关注；同时分子手性和超分子手性的表达、传递、存储及调节与生命现象相关联,因而成为了另一个研究热点。若将手性信息引到卟啉、酞菁分子上后,并使其在卟啉、酞菁分子及超分子水平上顺利表达出来,同时通过分子设计调节分子间作用力,最终获得希望得到的手性有机纳米结构材料,这对研究者而言仍是一个挑战。本论文主要设计、合成了带有手性的具有特定结构和性质的新型卟啉、酞菁化合物,并通过自组装方法得到了高级有序的手性纳米一维及三维结构,探讨了分级组装过程并提出了组装机理,研究了配位键对分子排列方式的影响,进而影响了聚集体的形貌以及超分子手性；还研究了不同类型的手性源所携带的手性信息在分子水平及超分子水平上的传递及表达；为通过调节弱作用力来调节纳米结构形貌以及了解手性信息的传递与表达提供了相关信息。另外还研究了手性卟啉的三阶非线性等光学性质,为手性卟啉在光学领域的应用提供了一定依据。其主要内容包括：
1.手性联二萘酚取代酞菁配合物组装纳米结构的研究
有机功能分子自组装或通过添加小分子物质组装得到的高级有序纳米结构在纳米科学及技术中将会获得广泛的应用,近年来通过分子间弱作用力作用进行纳米结构自组装的研究一直是广大科研工作者研究的热点。但对科学家来说,通过分子设计来调节分子间作用进而获得理想的形貌仍是一个不小的挑战。在本章中,我们以相应的配体在催化剂DBU和／或醋酸锌的存在下,合成了(R)-及(S)-构型的自由以及锌手性酞菁,即(R)-／(S)-四[11,12：13,14-二(1’,2’-萘)-1,4,7,10,15,18-(18-冠-6)-2,11,13-三烯]-自由酞菁[(R)-/(S)-H2Pc(1)]及相应的锌酞菁[(R)-/(S)-ZnPc(2)]。使用溶剂扩散法组装得到有机纳米聚集体,并通过紫外(UV)、圆二色(CD)、透射电镜(TEM)、扫描电镜(SEM)、X射线光电子能谱(XPS)等表征手段,研究比较了化合物1和2,以及化合物2在是否添加4,4’-联吡啶的情况下的组装性质,研究表明配位键的存在与否以及不同的配位键(配位能力)对聚集体的形貌存在较大影响。化合物1在手性取代基的影响下,通过π-π键等作用力聚集形成了长约3μm,宽约70nm,螺距约为125 nm的一维的左旋(R型)或右旋(S型)的螺旋纳米纤维结构；引入金属Zn后,在额外的Zn-O配位键作用下得到了微米级的实心球；添加4,4’-联吡啶后,由于锌酞菁的Zn与4,4’-联吡啶的N之间形成了Zn-N配位键(比Zn-O配位力强),聚集体又变成了一维的螺旋结构,但在长度(数十微米)、直径(约30nm)以及螺距(106nm)方面都与自由酞菁有很大不同。值得一提的是,化合物1和2(含4,4’-联吡啶)虽然最终都形成了螺旋纳米结构,但其初级结构表现出的手性方向(CD信号)是不同的；而未添加4,4’-联吡啶的化合物2虽然未形成手性结构,但其初级结构是有手性的。研究结果表明,手性基团的诱导效应和非共价键尤其是π-π堆积、金属配位键的协同作用在调节、控制酞菁分子自组装纳米结构中起着非常重要的作用,尤其是金属配位键对纳米结构的形貌、维度、手性及螺距大小的影响。其结论会为我们了解手性信息在超分子水平上的传递、表达及通过分子设计来制备、调控有机纳米功能材料提供有益的启示。
2.手性香茅醛取代卟啉光学性质的研究
手性在分子和超分子水平上的传递和表达一直是科学家们研究的热点之一,手性信息是否可以顺利传递和表达与手性源强度及传递距离有关。从目前的报道中可知在分子水平上,手性碳原子的手性难以传递到卟啉、酞菁等大环配合物上,即无CD响应。在本章中,我们以(+)-香茅醛和吡咯为原料,在催化剂三氟乙酸的存在下,合成了(R)-构型的自由卟啉5,10,15,20-四-(2,6-二甲基-5-庚烯)自由卟啉[(R)-H2T(C9H17)4P (1)],再以自由卟啉与醋酸锌反应得到了锌卟啉[(R)-ZnT(C9H17)4P (2)],使用溶剂扩散法得到了二者的聚集体溶液；并对二者的各种性质进行了相关的表征,包括氢谱、质谱、红外、紫外、荧光、圆二色及三阶非线性光学,着重研究了手性信息的传递与表达。研究表明,由于手性基团并未通过苯环而是直接连到卟啉环上的,既缩短了传递距离又排除了苯环的阻碍作用,在这种情况下,即使手性源较弱(手性碳原子),卟啉在分子水平上仍能显示出正的CD信号；形成聚集体后,出现了分裂的科顿效应,即在超分子水平上手性得到了顺利的表达并且手性信号得到了放大,值得一提的是化合物1和2具有相反的超分子手性是,说明虽然手性信息在化合物1和2的分子和超分子水平上都得到了顺利的传导和表达,但锌卟啉和自由卟啉的激子耦合方式是不同的。另外,当化合物发生聚集后,其紫外-可见吸收峰稍变宽、强度稍减小,同时发生了一定的迁移；荧光光谱发生了淬灭,这与大多数报导一致；三阶非线性光学性质在聚集后消失。其结果将会为我们研究手性在分子水平及超分子水平上的传递与表达提供一些相关信息,同时也为手性卟啉在光学领域的应用提供一定依据。
As novel functional materials, porphyrins and phthalocyanines have been expected to be widely application in materials science, such as molecular electronics, molecular information storage, and nonlinear optics, etc. Recently, to obtain ordered supramolecular aggregates and nano-scale assembly, besides the expression, transmission, storage and regulation of molecular/supramolecular's chirality, have attracted increasing attentions. lit must be pointed out that self-assembly of functional molecules into a prerequisite nanostructure with desirable dimension and morphology via controlling inter-molecular interaction and the introduced chirality informations still remains a great challenge for scientists. In order to investigate the hierarchical assembly, the role of coordination bond in tuning the aggregates's morphology and the expression of chiral information at molecular/supramolecular level, in this thesis several chiral porphyrins and phthalocyanines are designed and synthesized. Our research work has been focused on the following respects:
1. Helical Nano-structures Self-Assembled from Optically Active Phthalocyanine Derivatives Bearing Four Optically Active Binaphthyl Moieties:Effect of Metal-ligand Coordination on the Morphology, Dimension, and Helical Pitch of Self-Assembled Nano-structures
(R)-and (S)-Enantiomers of optically active metal free tetrakis [11,12:13,14-di(1',2'-naphtho)-1,4,7,10,15,18-hexaoxacycloeicosa-2,11,13-trieno]-ph thalocyanine and their zinc complexes, (R)-and (S)-H2Pc (1) and (R)-and (S)-ZnPc (2), were prepared from the tetramerization of corresponding phthalonitriles, (R)-and (S)-2,3-(4',5'-dicyanobenzo)-11,12:13,14-di(1',2'-naphtho)-1,4,7,10,15,18-hexaoxacycloeicosa-2,11,13-triene, in the absence and presence of Zn(OAc)2·2H2O template, respectively, promoted by organic base 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU). Their self-assembly behavior in the absence and presence of 4,4'-bipyridine has been comparatively investigated by electronic absorption and circular dichroism (CD) spectroscopy, transmission electron microscopy (TEM), scanning electron microscopy (SEM), X-ray diffraction (XRD) technique, and X-ray photoelectron spectroscopy (XPS). The metal free phthalocyanine self-assembles into highly ordered fibrous nano-structures (ca.3um length,70 nm width, and 125 nm helical pitch) with left-handed and right-handed helicity for (R)-1 and (S)-1, respectively, through the hierarchical manner via one-dimensional helices with chirality determined by the optically active binaphthyl side chains. In contrast, self-assembly of the phthalocyaninato zinc analogue leads to the formation of nano-particles. However, in the presence of 4,4'-bipyridine, additionally formed metal-ligand Zn-N(4,4-bipyridine) coordination bonds between the nitrogen atoms of additive 4,4'-bipyridine molecule and the zinc center of (R)-and (S)-2 molecules together withπ-πinteraction and chiral discrimination of chiral side chains induce a right-handed and left-handed helical arrangement in a stack of (R)-and (S)-2 molecules, respectively, which further hierarchically packs into highly ordered fibrous nano-structures of average tens of micrometer length,30 nm width, and 106 nm helical pitch with the same helicity to the stack, revealing the effect of metal-ligand coordination bonding interaction on the morphology, dimension, handedness, and the helical pitch of self-assembled nano-structures.
2. Synthesis, Circular Dichroism, and Third-Order Nonlinear Optical Properties of Optical Active Porphyrin Derivatives Bearing Four Meso Chiral Citronellal Moieties
A novel metal free meso-5,10,15,20-tetra-(2,6-dimethyl-5-heptenyl)porphyrin porphyrin [(R)-H2T(C9H17)4P (1)] with four chiral citronellal units attached at the meso positions of porphyrin and its zinc congener (R)-ZnT(C9H17)4P (2) have been designed, synthesized, and characterized. These two porphyrin compounds were characterized by 1HNMR, MS, third-order nonlinear optical (NLO) and various spectroscopic methods including IR, florescence, UV-vis and CD. Their florescence, UV-vis especially CD spectra changed after the formation of aggregates. Different from other porphyrin compounds containing chiral carbons, both metal free porphyrin and its zinc congener display positive CD signal in the Soret absorption region of porphyrin ligand, indicating effective chiral information transfer from the chiral citronellal tails to porphyrin chromophore at the molecular level. That's because the chiral citronellal tails were incorporated directly onto the meso positions instead of via meso-attached benzene ring. When self-assembled to aggregates, they displayed suparmolecular chirality with different directions.
1.手性联二萘酚取代酞菁配合物组装纳米结构的研究
有机功能分子自组装或通过添加小分子物质组装得到的高级有序纳米结构在纳米科学及技术中将会获得广泛的应用,近年来通过分子间弱作用力作用进行纳米结构自组装的研究一直是广大科研工作者研究的热点。但对科学家来说,通过分子设计来调节分子间作用进而获得理想的形貌仍是一个不小的挑战。在本章中,我们以相应的配体在催化剂DBU和／或醋酸锌的存在下,合成了(R)-及(S)-构型的自由以及锌手性酞菁,即(R)-／(S)-四[11,12：13,14-二(1’,2’-萘)-1,4,7,10,15,18-(18-冠-6)-2,11,13-三烯]-自由酞菁[(R)-/(S)-H2Pc(1)]及相应的锌酞菁[(R)-/(S)-ZnPc(2)]。使用溶剂扩散法组装得到有机纳米聚集体,并通过紫外(UV)、圆二色(CD)、透射电镜(TEM)、扫描电镜(SEM)、X射线光电子能谱(XPS)等表征手段,研究比较了化合物1和2,以及化合物2在是否添加4,4’-联吡啶的情况下的组装性质,研究表明配位键的存在与否以及不同的配位键(配位能力)对聚集体的形貌存在较大影响。化合物1在手性取代基的影响下,通过π-π键等作用力聚集形成了长约3μm,宽约70nm,螺距约为125 nm的一维的左旋(R型)或右旋(S型)的螺旋纳米纤维结构；引入金属Zn后,在额外的Zn-O配位键作用下得到了微米级的实心球；添加4,4’-联吡啶后,由于锌酞菁的Zn与4,4’-联吡啶的N之间形成了Zn-N配位键(比Zn-O配位力强),聚集体又变成了一维的螺旋结构,但在长度(数十微米)、直径(约30nm)以及螺距(106nm)方面都与自由酞菁有很大不同。值得一提的是,化合物1和2(含4,4’-联吡啶)虽然最终都形成了螺旋纳米结构,但其初级结构表现出的手性方向(CD信号)是不同的；而未添加4,4’-联吡啶的化合物2虽然未形成手性结构,但其初级结构是有手性的。研究结果表明,手性基团的诱导效应和非共价键尤其是π-π堆积、金属配位键的协同作用在调节、控制酞菁分子自组装纳米结构中起着非常重要的作用,尤其是金属配位键对纳米结构的形貌、维度、手性及螺距大小的影响。其结论会为我们了解手性信息在超分子水平上的传递、表达及通过分子设计来制备、调控有机纳米功能材料提供有益的启示。
2.手性香茅醛取代卟啉光学性质的研究
手性在分子和超分子水平上的传递和表达一直是科学家们研究的热点之一,手性信息是否可以顺利传递和表达与手性源强度及传递距离有关。从目前的报道中可知在分子水平上,手性碳原子的手性难以传递到卟啉、酞菁等大环配合物上,即无CD响应。在本章中,我们以(+)-香茅醛和吡咯为原料,在催化剂三氟乙酸的存在下,合成了(R)-构型的自由卟啉5,10,15,20-四-(2,6-二甲基-5-庚烯)自由卟啉[(R)-H2T(C9H17)4P (1)],再以自由卟啉与醋酸锌反应得到了锌卟啉[(R)-ZnT(C9H17)4P (2)],使用溶剂扩散法得到了二者的聚集体溶液；并对二者的各种性质进行了相关的表征,包括氢谱、质谱、红外、紫外、荧光、圆二色及三阶非线性光学,着重研究了手性信息的传递与表达。研究表明,由于手性基团并未通过苯环而是直接连到卟啉环上的,既缩短了传递距离又排除了苯环的阻碍作用,在这种情况下,即使手性源较弱(手性碳原子),卟啉在分子水平上仍能显示出正的CD信号；形成聚集体后,出现了分裂的科顿效应,即在超分子水平上手性得到了顺利的表达并且手性信号得到了放大,值得一提的是化合物1和2具有相反的超分子手性是,说明虽然手性信息在化合物1和2的分子和超分子水平上都得到了顺利的传导和表达,但锌卟啉和自由卟啉的激子耦合方式是不同的。另外,当化合物发生聚集后,其紫外-可见吸收峰稍变宽、强度稍减小,同时发生了一定的迁移；荧光光谱发生了淬灭,这与大多数报导一致；三阶非线性光学性质在聚集后消失。其结果将会为我们研究手性在分子水平及超分子水平上的传递与表达提供一些相关信息,同时也为手性卟啉在光学领域的应用提供一定依据。
As novel functional materials, porphyrins and phthalocyanines have been expected to be widely application in materials science, such as molecular electronics, molecular information storage, and nonlinear optics, etc. Recently, to obtain ordered supramolecular aggregates and nano-scale assembly, besides the expression, transmission, storage and regulation of molecular/supramolecular's chirality, have attracted increasing attentions. lit must be pointed out that self-assembly of functional molecules into a prerequisite nanostructure with desirable dimension and morphology via controlling inter-molecular interaction and the introduced chirality informations still remains a great challenge for scientists. In order to investigate the hierarchical assembly, the role of coordination bond in tuning the aggregates's morphology and the expression of chiral information at molecular/supramolecular level, in this thesis several chiral porphyrins and phthalocyanines are designed and synthesized. Our research work has been focused on the following respects:
1. Helical Nano-structures Self-Assembled from Optically Active Phthalocyanine Derivatives Bearing Four Optically Active Binaphthyl Moieties:Effect of Metal-ligand Coordination on the Morphology, Dimension, and Helical Pitch of Self-Assembled Nano-structures
(R)-and (S)-Enantiomers of optically active metal free tetrakis [11,12:13,14-di(1',2'-naphtho)-1,4,7,10,15,18-hexaoxacycloeicosa-2,11,13-trieno]-ph thalocyanine and their zinc complexes, (R)-and (S)-H2Pc (1) and (R)-and (S)-ZnPc (2), were prepared from the tetramerization of corresponding phthalonitriles, (R)-and (S)-2,3-(4',5'-dicyanobenzo)-11,12:13,14-di(1',2'-naphtho)-1,4,7,10,15,18-hexaoxacycloeicosa-2,11,13-triene, in the absence and presence of Zn(OAc)2·2H2O template, respectively, promoted by organic base 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU). Their self-assembly behavior in the absence and presence of 4,4'-bipyridine has been comparatively investigated by electronic absorption and circular dichroism (CD) spectroscopy, transmission electron microscopy (TEM), scanning electron microscopy (SEM), X-ray diffraction (XRD) technique, and X-ray photoelectron spectroscopy (XPS). The metal free phthalocyanine self-assembles into highly ordered fibrous nano-structures (ca.3um length,70 nm width, and 125 nm helical pitch) with left-handed and right-handed helicity for (R)-1 and (S)-1, respectively, through the hierarchical manner via one-dimensional helices with chirality determined by the optically active binaphthyl side chains. In contrast, self-assembly of the phthalocyaninato zinc analogue leads to the formation of nano-particles. However, in the presence of 4,4'-bipyridine, additionally formed metal-ligand Zn-N(4,4-bipyridine) coordination bonds between the nitrogen atoms of additive 4,4'-bipyridine molecule and the zinc center of (R)-and (S)-2 molecules together withπ-πinteraction and chiral discrimination of chiral side chains induce a right-handed and left-handed helical arrangement in a stack of (R)-and (S)-2 molecules, respectively, which further hierarchically packs into highly ordered fibrous nano-structures of average tens of micrometer length,30 nm width, and 106 nm helical pitch with the same helicity to the stack, revealing the effect of metal-ligand coordination bonding interaction on the morphology, dimension, handedness, and the helical pitch of self-assembled nano-structures.
2. Synthesis, Circular Dichroism, and Third-Order Nonlinear Optical Properties of Optical Active Porphyrin Derivatives Bearing Four Meso Chiral Citronellal Moieties
A novel metal free meso-5,10,15,20-tetra-(2,6-dimethyl-5-heptenyl)porphyrin porphyrin [(R)-H2T(C9H17)4P (1)] with four chiral citronellal units attached at the meso positions of porphyrin and its zinc congener (R)-ZnT(C9H17)4P (2) have been designed, synthesized, and characterized. These two porphyrin compounds were characterized by 1HNMR, MS, third-order nonlinear optical (NLO) and various spectroscopic methods including IR, florescence, UV-vis and CD. Their florescence, UV-vis especially CD spectra changed after the formation of aggregates. Different from other porphyrin compounds containing chiral carbons, both metal free porphyrin and its zinc congener display positive CD signal in the Soret absorption region of porphyrin ligand, indicating effective chiral information transfer from the chiral citronellal tails to porphyrin chromophore at the molecular level. That's because the chiral citronellal tails were incorporated directly onto the meso positions instead of via meso-attached benzene ring. When self-assembled to aggregates, they displayed suparmolecular chirality with different directions.
引文
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[14]为了更好地显示ZnPc(2)单体和聚集体(包括添加和未添加4,4’-联吡啶)的紫外-可见吸收光谱和圆二色光谱的区别,图2-4B和2-4E中的ZnPc单体UV-vis吸收是一样的,图2-4A和2-4B均是ZnPc单体的CD光谱。
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[14]为了更好地显示ZnPc(2)单体和聚集体(包括添加和未添加4,4’-联吡啶)的紫外-可见吸收光谱和圆二色光谱的区别,图2-4B和2-4E中的ZnPc单体UV-vis吸收是一样的,图2-4A和2-4B均是ZnPc单体的CD光谱。
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