集光与长寿命三重态的铱配合物的合成及应用
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摘要
IrⅢ配合物由于在电致发光、氧传感、三重态-三重态湮灭(TTA)上转换以及光催化等领域的广泛应用而成为研究的热点。然而传统的IrⅢ配合物在可见区的吸收很弱并且其三重激发态寿命很短,这严重影响了其在新兴的领域(光催化、光动力治疗和TTA上转换等)中的应用。本论文利用不同的有机荧光团合成了4个系列的IrⅢ配合物,借助稳态和瞬态光谱以及DFT理论计算等研究了其光物理性质并进行了应用研究。
首先将萘酰亚胺(NI)通过炔键分别连接到2-苯基吡啶(ppy)和2，2’-联吡啶(bpy)上合成了2-3和2-4。与2-1相比,2-3在402nm处的吸收增强了3倍。瞬态吸收光谱、77K发射光谱和自旋密度分布都表明2-3和2-4的最低三重激发态(T1)为NI的三重激发态(3IL*),而2-1的T1态是金属向配体电荷转移的三重态(3MLCT*)。2-1-2-4在氧传感和TTA上转换中的应用研究表明：2-4对O2的敏感性与2-1相比提高了156倍；2-3的TTA上转换效率达到14.4%,而2-1没有上转换能力。
其次将香豆素(cou)与1,10-邻菲罗啉(phen)之间通过咪唑环(Im)连接合成了3-3和3-4。与3-1相比,3-3在466nm处的吸光能力提高了150倍。研究结果表明3-3和3-4的T1态为香豆素的3IL*态,而3-1的T1态是3MLCT*。TTA上转换和光氧化研究表明：3-3和3-4的TTA上转换效率分别达到21.3%和23.4%,而3-1在相同的条件下没有上转换能力；与3-1相比,3-3和3-4的光氧化速率明显加快,产率明显提高。
为了研究IrⅢ中心原子和有机荧光团之间不同的连接方式对其性质的影响,本文将氟硼吡咯(Bodipy)通过炔键连接到bpy上合成了4-2(Bodipy苯环的meso位通过炔键连接到IrⅢ中心心原子)和4-3(Bodipy的π核的2位通过炔键连接到IrⅢ中心原子)。与4-1相比,4-3在527nm处的吸收增强了152倍。研究结果表吸4-2和4-3的T1态均为Bodipy的3IL*态,而4-1的T1态为3MLCT*。4-2和4-3的TTA上转换效率分别为1.2%和2.8%,而4-1在同样条件下没有上转换能力。另外与4-1相比,4-2和4-3的光氧化能力明显提高。实验结果还证明4-3比4-2的性质更加优异。
本文最后选用花二酰亚胺(PBI)合成了5-1和PBI的港湾位用胺基取代的5-2。与4-1相比,5-1在541nm处的吸收增强了70倍；5-2的最大吸收波长红移到669nm。研究结果表明5-1和5-2的T1态也是3IL*态。光氧化研究结果表明：5-1和5-2做敏化剂时的光氧化速率与4-1相比明显加快,产率也明显提高。
IrⅢ complexes have attracted much attention owing to their applicabilities in electroluminescence, oxygen sensing, triplet-triplet annihilation (TTA) upconversion and photocatalysis. However, traditional IrⅢ complexes show weak absorption of visible light and short triplet excited state lifetimes that affects the newly developed applications (photocatalysis, photodynamic therapy and TTA upconversion) seriously. In this thesis, four series of IrⅢ complexes were synthesized by using different organic chromophores. The photophysical properties and applications of the complexes were studied by steady and transient spectra, as well as DFT calculations.
Firstly,2-3and2-4were synthesized by attaching naphthalimide (NI) to ppy or bpy. The absorption of2-3was improved by3-fold at402nm compared to2-1. The low-lying triplet excited states (T1) of2-3and2-4were proved to be triplet excited states (3IL*) of NI while that of2-1was metal to ligand charge transfer triplet excited state (3MLCT*) by transient difference absorption spectra,77K emission spectra and spin density analysis. The application of2-1-2-4in oxygen sensing and TTA upconversion indicated that luminescent O2sensitivity of2-4was improved by156-fold than that of2-1; TTA upconversion quantum yield of14.4%was observed for2-3, whereas the upconversion was neglectable for2-1at the same experimental conditions.
Furthermore,3-3and3-4were synthesized by attaching coumarin (cou) to1,10-Phenanthroline (phen) via imidazole (Im). The absorption of3-3was improved by150-fold at466nm compared to3-1at the same wavelength. The T1states of3-3and3-4were proved to be3TL*state while that of3-1was3MLCT*state. The applications in TTA upconversion and photooxidation showed that upconversion quantum yields of21.3%and23.4%were observed for3-3and3-4respectively, whereas the upconversion was neglectable for3-1at the same experimental conditions. The photooxidation rates of3-3and3-4were much faster than3-1and the yields were also improved.
In order to study the effects of different linkers between IrⅢ coordination centre and organic chromophore,4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (Bodipy) was attached to bpy to prepare4-2(the meso-pheny1of Bodipy was attached to the IrⅢ coordination centre via π-conjugation linker) and4-3(2-position of π-core of Bodipy was attached to IrⅢ coordination centre via π-conjugation linker). The absorption of4-3was improved by 152-fold at527nm compared to4-1at the same wavelength. The T1states of4-2and4-3were proved to be3IL*state while that of4-1was3MLCT*state. The upconvcrsion quantum yields of4-2and4-3were1.2%and2.8%respectively, whereas the upconversion was neglectable for4-1at the same experimental conditions. The performance of photooxidation with4-2and4-3as photosensitizers was much better than4-1. The experiments results showed that the property of4-3was better than that of4-2.
Lastly, perylenebisimide (PBI) was chosed to prepare5-1. Furthermore, with substitution of the bay position of PBI by amino group,5-2was prepared. The absorption of5-1was improved by70-fold at541nm compared to4-1at the same wavelength. The absorption wavelength of5-2is red-shift to669nm. The T1states of5-1and5-2were also proved to be3IL*state by the experiments results. The photooxidation results indicated that photooxidation rates with5-1and5-2as triplet photosensitizers were much faster and the yields were much higher than that with4-1as photosensitizers.
首先将萘酰亚胺(NI)通过炔键分别连接到2-苯基吡啶(ppy)和2，2’-联吡啶(bpy)上合成了2-3和2-4。与2-1相比,2-3在402nm处的吸收增强了3倍。瞬态吸收光谱、77K发射光谱和自旋密度分布都表明2-3和2-4的最低三重激发态(T1)为NI的三重激发态(3IL*),而2-1的T1态是金属向配体电荷转移的三重态(3MLCT*)。2-1-2-4在氧传感和TTA上转换中的应用研究表明：2-4对O2的敏感性与2-1相比提高了156倍；2-3的TTA上转换效率达到14.4%,而2-1没有上转换能力。
其次将香豆素(cou)与1,10-邻菲罗啉(phen)之间通过咪唑环(Im)连接合成了3-3和3-4。与3-1相比,3-3在466nm处的吸光能力提高了150倍。研究结果表明3-3和3-4的T1态为香豆素的3IL*态,而3-1的T1态是3MLCT*。TTA上转换和光氧化研究表明：3-3和3-4的TTA上转换效率分别达到21.3%和23.4%,而3-1在相同的条件下没有上转换能力；与3-1相比,3-3和3-4的光氧化速率明显加快,产率明显提高。
为了研究IrⅢ中心原子和有机荧光团之间不同的连接方式对其性质的影响,本文将氟硼吡咯(Bodipy)通过炔键连接到bpy上合成了4-2(Bodipy苯环的meso位通过炔键连接到IrⅢ中心心原子)和4-3(Bodipy的π核的2位通过炔键连接到IrⅢ中心原子)。与4-1相比,4-3在527nm处的吸收增强了152倍。研究结果表吸4-2和4-3的T1态均为Bodipy的3IL*态,而4-1的T1态为3MLCT*。4-2和4-3的TTA上转换效率分别为1.2%和2.8%,而4-1在同样条件下没有上转换能力。另外与4-1相比,4-2和4-3的光氧化能力明显提高。实验结果还证明4-3比4-2的性质更加优异。
本文最后选用花二酰亚胺(PBI)合成了5-1和PBI的港湾位用胺基取代的5-2。与4-1相比,5-1在541nm处的吸收增强了70倍；5-2的最大吸收波长红移到669nm。研究结果表明5-1和5-2的T1态也是3IL*态。光氧化研究结果表明：5-1和5-2做敏化剂时的光氧化速率与4-1相比明显加快,产率也明显提高。
IrⅢ complexes have attracted much attention owing to their applicabilities in electroluminescence, oxygen sensing, triplet-triplet annihilation (TTA) upconversion and photocatalysis. However, traditional IrⅢ complexes show weak absorption of visible light and short triplet excited state lifetimes that affects the newly developed applications (photocatalysis, photodynamic therapy and TTA upconversion) seriously. In this thesis, four series of IrⅢ complexes were synthesized by using different organic chromophores. The photophysical properties and applications of the complexes were studied by steady and transient spectra, as well as DFT calculations.
Firstly,2-3and2-4were synthesized by attaching naphthalimide (NI) to ppy or bpy. The absorption of2-3was improved by3-fold at402nm compared to2-1. The low-lying triplet excited states (T1) of2-3and2-4were proved to be triplet excited states (3IL*) of NI while that of2-1was metal to ligand charge transfer triplet excited state (3MLCT*) by transient difference absorption spectra,77K emission spectra and spin density analysis. The application of2-1-2-4in oxygen sensing and TTA upconversion indicated that luminescent O2sensitivity of2-4was improved by156-fold than that of2-1; TTA upconversion quantum yield of14.4%was observed for2-3, whereas the upconversion was neglectable for2-1at the same experimental conditions.
Furthermore,3-3and3-4were synthesized by attaching coumarin (cou) to1,10-Phenanthroline (phen) via imidazole (Im). The absorption of3-3was improved by150-fold at466nm compared to3-1at the same wavelength. The T1states of3-3and3-4were proved to be3TL*state while that of3-1was3MLCT*state. The applications in TTA upconversion and photooxidation showed that upconversion quantum yields of21.3%and23.4%were observed for3-3and3-4respectively, whereas the upconversion was neglectable for3-1at the same experimental conditions. The photooxidation rates of3-3and3-4were much faster than3-1and the yields were also improved.
In order to study the effects of different linkers between IrⅢ coordination centre and organic chromophore,4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (Bodipy) was attached to bpy to prepare4-2(the meso-pheny1of Bodipy was attached to the IrⅢ coordination centre via π-conjugation linker) and4-3(2-position of π-core of Bodipy was attached to IrⅢ coordination centre via π-conjugation linker). The absorption of4-3was improved by 152-fold at527nm compared to4-1at the same wavelength. The T1states of4-2and4-3were proved to be3IL*state while that of4-1was3MLCT*state. The upconvcrsion quantum yields of4-2and4-3were1.2%and2.8%respectively, whereas the upconversion was neglectable for4-1at the same experimental conditions. The performance of photooxidation with4-2and4-3as photosensitizers was much better than4-1. The experiments results showed that the property of4-3was better than that of4-2.
Lastly, perylenebisimide (PBI) was chosed to prepare5-1. Furthermore, with substitution of the bay position of PBI by amino group,5-2was prepared. The absorption of5-1was improved by70-fold at541nm compared to4-1at the same wavelength. The absorption wavelength of5-2is red-shift to669nm. The T1states of5-1and5-2were also proved to be3IL*state by the experiments results. The photooxidation results indicated that photooxidation rates with5-1and5-2as triplet photosensitizers were much faster and the yields were much higher than that with4-1as photosensitizers.
引文
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