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Optical and Electrochemical Properties of Indotricarbocyanine Dyes for Photodynamic Therapy
Journal of Applied Spectroscopy ( IF 0.8 ) Pub Date : 2021-07-16 , DOI: 10.1007/s10812-021-01198-0
H. M. Maltanava 1 , S. K. Poznyak 1 , N. V. Belko 2 , M. P. Samtsov 2
Affiliation  

The effect of the molecular structure of indotricarbocyanine dyes on their luminescence spectral and redox properties was studied. The introduction of a chlorine-substituted bridge into the polymethine chain leads to a significant hypsochromic shift of the absorption and fluorescence spectra, whereas change in the structure of substituents at the indolenine terminal groups only has a weak effect on the spectra. The electrochemical properties of the polymethine dyes were studied by cyclic voltammetry. The oxidation and reduction potentials of the dyes were determined, and the corresponding energies of the highest occupied and lowest unoccupied molecular orbitals were calculated. Reduction of the molecules of the dye is an irreversible process, whereas the reversibility of the oxidation process depends on the structure of the polymethine chain and the nature of the counterion. Introduction of a chlorine–orthophenylene bridge into the polymethine chain leads to a significant increase in the reversibility of the oxidation reaction of the dyes on account of increase in the stability of the dication-radicals. It was shown that oxidation of the bromide ions occurs at lower potentials compared with oxidation of the dyes with a substituted polymethine chain, which probably leads to decrease in the reversibility of electrochemical oxidation of the dyes when bromide ions are present in solution.



中文翻译:

用于光动力治疗的吲哚三碳菁染料的光学和电化学性质

研究了吲哚三碳菁染料的分子结构对其发光光谱和氧化还原性能的影响。在聚次甲基链中引入一个氯取代的桥会导致吸收和荧光光谱的显着减色偏移,而假吲哚端基取代基结构的变化对光谱的影响很小。通过循环伏安法研究了聚甲川染料的电化学性质。确定了染料的氧化和还原电位,并计算了最高占据和最低未占据分子轨道的相应能量。染料分子的还原是一个不可逆的过程,而氧化过程的可逆性取决于聚次甲基链的结构和反离子的性质。由于二阳离子自由基稳定性的增加,将氯-邻苯桥引入聚次甲基链导致染料氧化反应的可逆性显着增加。结果表明,与具有取代聚次甲基链的染料氧化相比,溴离子的氧化发生在较低的电位下,这可能导致溶液中存在溴离子时染料电化学氧化的可逆性降低。由于二阳离子自由基稳定性的增加,将氯-邻苯桥引入聚次甲基链导致染料氧化反应的可逆性显着增加。结果表明,与具有取代聚次甲基链的染料氧化相比,溴离子的氧化发生在较低的电位下,这可能导致溶液中存在溴离子时染料电化学氧化的可逆性降低。由于二阳离子自由基稳定性的增加,将氯-邻苯桥引入聚次甲基链导致染料氧化反应的可逆性显着增加。结果表明,与具有取代聚次甲基链的染料氧化相比,溴离子的氧化发生在较低的电位下,这可能导致溶液中存在溴离子时染料电化学氧化的可逆性降低。

更新日期:2021-07-16
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