卟啉、酞菁与富勒烯及碳纳米管给受体体系的构筑及性质研究
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摘要
为了模拟光合作用,实现太阳能的有效利用,近年来,给受体系统的光诱导电子转移成为研究的热点。卟啉、酞菁以及富勒烯和碳纳米管由于其独特的结构和优良的光电化学性质,是人工模拟光合作用首选的给受体,由它们构筑的给受体体系在光电转换和分子器件中具有潜在的应用价值。本文利用卟啉和酞菁作为电子给体,富勒烯与单壁碳纳米管作为电子受体,构筑了多种给受体体系,并对其结构进行了表征,研究了其光物理和电化学性质,并取得了长寿命的电荷分离态。具体内容如下：
合成和表征了酰胺键共价连接的酞菁—富勒烯二元体系。紫外可见吸收光谱和荧光光谱研究表明,二元体系内部给受体之间在基态下存在弱的而在激发态下存在较强的相互作用。时间分辨荧光、瞬时吸收光谱和电化学研究证实这种作用主要来自酞菁和富勒烯之间的光诱导电子转移。通过开孔z-扫描的方法研究了酞菁—富勒烯二元体系的非线性吸收性质。相对于富勒烯和酞菁前体,酞菁—富勒烯二元体系有着更好的光学非线性效应。说明这种通过酰胺键相连的扩大的π电子共轭体系以及酞菁与富勒烯给受体之间的光诱导电子转移,在一定程度上有助于体系非线性光学性质的提高,基于此可以设计宽带的光限幅材料。
利用共价键连接的二茂铁—酞菁二元体系与带有吡啶或咪唑基的富勒烯吡咯烷衍生物轴向配位,成功构筑了二茂铁—酞菁—富勒烯超分子三元体系。通过紫外—可见光谱滴定法确定了其配位稳定性。稳态和时间分辨荧光光谱研究表明,在该超分子三元体系中发生了快速的光诱导电子转移,并具有较高的电荷分离态量子产率。循环伏安法数据表明其电荷分离驱动力△Gcs为负值,说明酞菁和富勒烯之间容易形成电荷分离态。
制备了共价连接的二茂铁—卟啉—单壁碳纳米管(Fc-H2P-SWNTs)三元复合物,通过FT-IR.Raman.AFM和TEM对其结构进行了详尽的表征。用TGA和XPS方法估算了复合物中二茂铁键连卟啉的相对含量(51-57%)。通过光物理方法估算了单壁碳纳米管复合物在DMF溶液中的溶解度(234 mg·L-1)。紫外可见吸收、稳态和时间分辨荧光光谱实验表明复合物中二茂铁、卟啉和碳纳米管之间发生了光诱导电子转移。用纳秒激光闪光光解的方法观察了复合物的瞬态吸收光谱,证明产生了64.5μs长寿命的电荷分离态(Fc+-H2P)m-x-SWNTs(m-x)·-(Fc-H2P)n-m+x.
构筑了卟啉和酞菁同时共价修饰的SWNTs复合物,并对其进行了详尽的表征。与参照化合物相比,复合物中卟啉和酞菁的荧光几乎被键连的碳纳米管全部猝灭,说明卟啉和酞菁与单壁碳纳米管之间发生了电子或能量转移。该复合物溶解性相对较高(309 mg·L-1),并且具有较宽的吸光范围,这有利于其在电极表面较好地成膜及对太阳光的有效利用,从而改善光电器件的性能。
合成了主链含有卟啉和富勒烯的聚酰胺,通过FT-IR,UV-Vis、固体碳谱以及AFM和TEM对其进行详尽的表征。用凝胶渗透色谱GPC确定了聚酰胺的分子量,并通过热失重TGA研究了聚合物的热稳定性。稳态和时间分辨荧光光谱研究表明,在聚酰胺中发生了卟啉和富勒烯之间快速的光诱导电子转移,并具有较高的电荷分离态量子产率(≥85%)。瞬时吸收光谱进一步证实,通过激发单线态卟啉和富勒烯之间的多步光诱导电子转移,产生约100μs长寿命的电荷分离态。电荷分离与电荷重组速率之比kCS/kCR-10000,表明在光诱导电子转移中具有较高的电荷分离态稳定性。
这些结果说明制备的上述给受体体系在光电转换材料等领域具有潜在的应用前景。
Much attention has been paid to the studies on photoinduced electron transfer (PET) in donor-acceptor systems recently mainly to develop artificial photosynthetic systems, in which porphyrin (Por)/phthalocyanine (Pc) and [60]fullerene (C60)/ carbon nanotube (CNT) are considered as attractive molecular components due to their unique structures and rich photoelectronic properties. The Por/Pc—60/CNT system has been proved to be a potential candidate for solar energy conversion materials and molecular devices. Here, a series of ensembles based on the donor Por/Pc and acceptor C60/CNT were constructed and fully characterized. The photophysical and electrochemical properties of the novel donor-acceptor ensembles were studied, and the long-lived charge separated states have been achieved. The important results obtained are described as follows:
1. A new amide-linked phthalocyanine-fullerene dyad (ZnPc-C60) is reported. Steady-state, time-resolved fluorescence and transient absorption measurements showed the occurrence of PET from the singlet excited phthalocyanine to fullerene with large driving force(△GCS).The larger nonlinear absorption of ZnPc-C60,better than fullerene (C60) and the control sample, was observed by the Z-scan experiments, which indicated the synergistic effect of two active moieties in the dyad.
2. Ferrocene-phthalocyanine-fullerene supramolecular triads have been constructed with pyridine-or imidazole-appended fulleropyrrolidine and covalently linked zinc phthalocyanine-ferrocene dyad via axial coordination. The stablilities of the triads (Kassoc-8.58×104 mol-1·L) were studied by optical absorption methods. Steady-state and time-resolved fluorescence measurements suggested that the occurrence of efficient PET (kCS-109 s-1) from excited phthalocyanine to fullerene entity in the triads with high charge-separation quantum yields (ΦCS-0.88). The redox potentials were determined by cyclic voltammetric, and the driving forces (△GCS--0.60 eV) were estimated to be exothermic, which favored the forming of charge-separation state.
3. Novel covalent-linked ferrocene-porphyrin-SWNTs triads hybrid have been synthesized and fully characterized by IR, Raman, AFM and TEM. The amount of functional groups in the triads hybrid were roughly estimated to be around 51-57% by TGA and XPS analysis. The considerable porphyrin attachment significantly improved the solubility (234 mg-L-1) and dispersion stability of the SWNTs in organic solvents. The UV-Vis absorption and fluorescence spectra of the nanohybrid indicated the weak in ground state and strong in excited state electronic interaction between donors (porphyrin containing ferrocene) and the extendedπ-system of SWNTs acceptors. The PET reactions from porphyrin to C60 in the triads hybrid were observed in fluorescence lifetime and nanosecond laser-flash photolysis experiments, which confirmed to form long-lived (64.5μs) charge separated state (Fc+-H2P)m-x-SWNTs(m-x)·-(Fc-H2P)n-m+x.
4. Novel covalently functionalized SWNTs simultaneity with two kinds of chromophores (porphyrin and phthalocyanine) have been synthesized and characterized. The UV-Vis absorption and fluorescence spectra of the nanohybrid indicated the weak in ground state and strong in excited state electronic interaction between donors (porphyrin and phthalocyanine moieties) and the extendedπ-system of SWNTs acceptors. This novel nanohybrid material exhibited wider spectral region and more excellent solubility (309 mg-L-1) compared to those of either porphyrin or phthalocyanine functionalized SWNTs, which was favorable for the good film formation on the electrode and the effective utilization of solar energy, hence the performance of devices might be improved greatly.
5. Conjugated polyamides containing porphyrin and C6o in the main chain were prepared and characterized. Gel permeation chromatography (GPC) analysis of the polyamides showed the weight-average molecular weight of about 2.37×104. The temperature at 5% weight loss determined by thermogravimetric analysis (TGA) was above 216℃. Atomic force microscopy (AFM) images displayed the flat round-shaped aggregation structure of the polyamides. The photophysical properties were studied by UV-Visible, fluorescence spectroscopy, and fluorescence lifetime. The PET reactions from porphyrin to C6o in the polyamides were observed in nanosecond laser-flash photolysis experiments, which confirmed to form charge separated state (porphyrin radical cation-C60 radical anion pair) with a lifetime about 100μs. The calculated ratio of kcs/kcR was found to be-10000 indicating the high charge stabilization in the PET process.
The results showed that all above donor-acceptor systems were potential solar energy conversion materials.
合成和表征了酰胺键共价连接的酞菁—富勒烯二元体系。紫外可见吸收光谱和荧光光谱研究表明,二元体系内部给受体之间在基态下存在弱的而在激发态下存在较强的相互作用。时间分辨荧光、瞬时吸收光谱和电化学研究证实这种作用主要来自酞菁和富勒烯之间的光诱导电子转移。通过开孔z-扫描的方法研究了酞菁—富勒烯二元体系的非线性吸收性质。相对于富勒烯和酞菁前体,酞菁—富勒烯二元体系有着更好的光学非线性效应。说明这种通过酰胺键相连的扩大的π电子共轭体系以及酞菁与富勒烯给受体之间的光诱导电子转移,在一定程度上有助于体系非线性光学性质的提高,基于此可以设计宽带的光限幅材料。
利用共价键连接的二茂铁—酞菁二元体系与带有吡啶或咪唑基的富勒烯吡咯烷衍生物轴向配位,成功构筑了二茂铁—酞菁—富勒烯超分子三元体系。通过紫外—可见光谱滴定法确定了其配位稳定性。稳态和时间分辨荧光光谱研究表明,在该超分子三元体系中发生了快速的光诱导电子转移,并具有较高的电荷分离态量子产率。循环伏安法数据表明其电荷分离驱动力△Gcs为负值,说明酞菁和富勒烯之间容易形成电荷分离态。
制备了共价连接的二茂铁—卟啉—单壁碳纳米管(Fc-H2P-SWNTs)三元复合物,通过FT-IR.Raman.AFM和TEM对其结构进行了详尽的表征。用TGA和XPS方法估算了复合物中二茂铁键连卟啉的相对含量(51-57%)。通过光物理方法估算了单壁碳纳米管复合物在DMF溶液中的溶解度(234 mg·L-1)。紫外可见吸收、稳态和时间分辨荧光光谱实验表明复合物中二茂铁、卟啉和碳纳米管之间发生了光诱导电子转移。用纳秒激光闪光光解的方法观察了复合物的瞬态吸收光谱,证明产生了64.5μs长寿命的电荷分离态(Fc+-H2P)m-x-SWNTs(m-x)·-(Fc-H2P)n-m+x.
构筑了卟啉和酞菁同时共价修饰的SWNTs复合物,并对其进行了详尽的表征。与参照化合物相比,复合物中卟啉和酞菁的荧光几乎被键连的碳纳米管全部猝灭,说明卟啉和酞菁与单壁碳纳米管之间发生了电子或能量转移。该复合物溶解性相对较高(309 mg·L-1),并且具有较宽的吸光范围,这有利于其在电极表面较好地成膜及对太阳光的有效利用,从而改善光电器件的性能。
合成了主链含有卟啉和富勒烯的聚酰胺,通过FT-IR,UV-Vis、固体碳谱以及AFM和TEM对其进行详尽的表征。用凝胶渗透色谱GPC确定了聚酰胺的分子量,并通过热失重TGA研究了聚合物的热稳定性。稳态和时间分辨荧光光谱研究表明,在聚酰胺中发生了卟啉和富勒烯之间快速的光诱导电子转移,并具有较高的电荷分离态量子产率(≥85%)。瞬时吸收光谱进一步证实,通过激发单线态卟啉和富勒烯之间的多步光诱导电子转移,产生约100μs长寿命的电荷分离态。电荷分离与电荷重组速率之比kCS/kCR-10000,表明在光诱导电子转移中具有较高的电荷分离态稳定性。
这些结果说明制备的上述给受体体系在光电转换材料等领域具有潜在的应用前景。
Much attention has been paid to the studies on photoinduced electron transfer (PET) in donor-acceptor systems recently mainly to develop artificial photosynthetic systems, in which porphyrin (Por)/phthalocyanine (Pc) and [60]fullerene (C60)/ carbon nanotube (CNT) are considered as attractive molecular components due to their unique structures and rich photoelectronic properties. The Por/Pc—60/CNT system has been proved to be a potential candidate for solar energy conversion materials and molecular devices. Here, a series of ensembles based on the donor Por/Pc and acceptor C60/CNT were constructed and fully characterized. The photophysical and electrochemical properties of the novel donor-acceptor ensembles were studied, and the long-lived charge separated states have been achieved. The important results obtained are described as follows:
1. A new amide-linked phthalocyanine-fullerene dyad (ZnPc-C60) is reported. Steady-state, time-resolved fluorescence and transient absorption measurements showed the occurrence of PET from the singlet excited phthalocyanine to fullerene with large driving force(△GCS).The larger nonlinear absorption of ZnPc-C60,better than fullerene (C60) and the control sample, was observed by the Z-scan experiments, which indicated the synergistic effect of two active moieties in the dyad.
2. Ferrocene-phthalocyanine-fullerene supramolecular triads have been constructed with pyridine-or imidazole-appended fulleropyrrolidine and covalently linked zinc phthalocyanine-ferrocene dyad via axial coordination. The stablilities of the triads (Kassoc-8.58×104 mol-1·L) were studied by optical absorption methods. Steady-state and time-resolved fluorescence measurements suggested that the occurrence of efficient PET (kCS-109 s-1) from excited phthalocyanine to fullerene entity in the triads with high charge-separation quantum yields (ΦCS-0.88). The redox potentials were determined by cyclic voltammetric, and the driving forces (△GCS--0.60 eV) were estimated to be exothermic, which favored the forming of charge-separation state.
3. Novel covalent-linked ferrocene-porphyrin-SWNTs triads hybrid have been synthesized and fully characterized by IR, Raman, AFM and TEM. The amount of functional groups in the triads hybrid were roughly estimated to be around 51-57% by TGA and XPS analysis. The considerable porphyrin attachment significantly improved the solubility (234 mg-L-1) and dispersion stability of the SWNTs in organic solvents. The UV-Vis absorption and fluorescence spectra of the nanohybrid indicated the weak in ground state and strong in excited state electronic interaction between donors (porphyrin containing ferrocene) and the extendedπ-system of SWNTs acceptors. The PET reactions from porphyrin to C60 in the triads hybrid were observed in fluorescence lifetime and nanosecond laser-flash photolysis experiments, which confirmed to form long-lived (64.5μs) charge separated state (Fc+-H2P)m-x-SWNTs(m-x)·-(Fc-H2P)n-m+x.
4. Novel covalently functionalized SWNTs simultaneity with two kinds of chromophores (porphyrin and phthalocyanine) have been synthesized and characterized. The UV-Vis absorption and fluorescence spectra of the nanohybrid indicated the weak in ground state and strong in excited state electronic interaction between donors (porphyrin and phthalocyanine moieties) and the extendedπ-system of SWNTs acceptors. This novel nanohybrid material exhibited wider spectral region and more excellent solubility (309 mg-L-1) compared to those of either porphyrin or phthalocyanine functionalized SWNTs, which was favorable for the good film formation on the electrode and the effective utilization of solar energy, hence the performance of devices might be improved greatly.
5. Conjugated polyamides containing porphyrin and C6o in the main chain were prepared and characterized. Gel permeation chromatography (GPC) analysis of the polyamides showed the weight-average molecular weight of about 2.37×104. The temperature at 5% weight loss determined by thermogravimetric analysis (TGA) was above 216℃. Atomic force microscopy (AFM) images displayed the flat round-shaped aggregation structure of the polyamides. The photophysical properties were studied by UV-Visible, fluorescence spectroscopy, and fluorescence lifetime. The PET reactions from porphyrin to C6o in the polyamides were observed in nanosecond laser-flash photolysis experiments, which confirmed to form charge separated state (porphyrin radical cation-C60 radical anion pair) with a lifetime about 100μs. The calculated ratio of kcs/kcR was found to be-10000 indicating the high charge stabilization in the PET process.
The results showed that all above donor-acceptor systems were potential solar energy conversion materials.
引文
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