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首页> 外文期刊>RSC Advances >Synthesis and photophysical studies of an indigo derivative: N-octyl-7,7′-diazaindigo
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Synthesis and photophysical studies of an indigo derivative: N-octyl-7,7′-diazaindigo

机译：靛蓝衍生物的合成与光药研究：N-Octyl-7,7'-Diazaindigo

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In this paper, we explore the synthesis, characterization, and photophysical properties of a novel indigo derivative, N -octyl-7,7′-diazaindigo, being the first time that diazaindigos have been studied as photophysically-active chemical entities. Reduction of the neutral “keto-form” to the so-called “leuco-form” changes the global spectroscopic and photophysical behaviors. Both species have been investigated by different photophysical studies, such as analysis of absorption and emission spectra, fluorescence quantum yields ( Φ _(F) ) and lifetimes. Finally, to appraise in depth the deactivation of the excited state of the keto form, femtosecond transient absorption (TA) experiments and Density Functional Theory (DFT) and Time Dependent (TD)-DFT calculations were performed. In an organic aprotic solvent ( N , N -dimethylformamide), TA experiments showed a fast deactivation channel ( τ _(1) = 2.9 ps), which was ascribed to solvent reorganization, and a longer decay component ( τ _(2) = 86 ps) associated with an internal conversion (IC) process to the ground-state, in opposition to the excited state proton transfer (ESPT) mechanism that takes place in the indigo molecules but in protic solvents. A comparative study was also carried out on the parent molecule, 7,7′-diazaindigo, corroborating the previous conclusions obtained for the alkyl derivative. In agreement with experimental observations, DFT and TD-DFT calculations revealed that the deactivation of the S _(1) state of the keto form takes place through an internal conversion process.
机译：在本文中，我们探讨了一种新型靛蓝衍生物N-乙基-7,7'-二Zaindigo的合成，表征和光物理性质，是首次研究了Diazaindigos作为光学活性的化学实体。将中性“酮形式”的减少到所谓的“leuco形式”改变全局光谱和光物理行为。通过不同的光学研究已经研究了这两种物种，例如吸收和发射光谱的分析，荧光量子产率（φ_（f））和寿命。最后，对深度进行评估，进行酮形式的激发状态，飞秒瞬态吸收（TA）实验和密度泛函理论（DFT）和时间依赖性（TD）-DFT计算。在有机非质子溶剂（N，N-二甲基甲酰胺）中，TA实验显示出快速停用通道（τ_（1）= 2.9 ps），其归因于溶剂重组，更长的衰减组分（τ_（2）= 86 ps）与地面转换（IC）过程相关联，与地态相反，在靛蓝分子中，但在质子溶剂中发生兴奋状态质子转移（ESPT）机制。还对母体分子，7,7'-二氮二甙进行了比较研究，证实了对烷基衍生物获得的前一个结论。在实验观察结果中，DFT和TD-DFT计算表明，通过内部转换过程发生了keTo形式的S _（1）状态的停用。

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