Optoelectronically active luminescent valine‐substituted perylene diimide: structure‐property correlation via spectroscopic and density functional approaches,Journal of Physical Organic Chemistry

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Optoelectronically active luminescent valine‐substituted perylene diimide: structure‐property correlation via spectroscopic and density functional approaches
Journal of Physical Organic Chemistry ( IF 1.9 ) Pub Date : 2020-06-29 , DOI: 10.1002/poc.4095
Geeta Durga ₁ , Vinay K. Verma ₁ , Richa Tomar ₁ , Roopali Prajapati ₁ , Vishakha Chauhan ₁ , Nikhil Aggarwal ₁

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In literature, the applicability of solution‐phase perylene diimides (PDIs) semiconductors are limited due to their restricted solubility in solvents. In contrast, we synthesized a highly soluble and novel valine‐functionalized PDI derivative (perylene diimide diacid, PDIDA) whose optical and electrical properties were carefully assessed by experimental and density functional approaches. Notably, on valine substitution, the ultraviolet‐visible absorption band centered at 524 nm was attributed to the predominant HOMO ➔ LUMO electronic transition (weighing coefficient = 99 %). Interestingly, the nonuniform variation (W‐shaped) in absorption energy for HOMO ➔ LUMO electronic transition in PDIDA with solvent dielectric constant was experimentally witnessed. The latter was computationally attributed to the more S₁ stabilization over S_o solvent stabilization, particularly in ethanol and dimethyl sulfoxide (DMSO). Furthermore, upon 525 nm excitation, the maximum fluorescence emission was observed at 533 nm with photoluminescence quantum yield as high as 0.77. Interestingly, similar to absorption studies, pronounced influence of solvent polarity was evident on the emission maximum particularly in ethanol and DMSO. Subsequently, electrochemical investigation proved that the PDIDA sustained the intrinsic n‐type semiconductivity with a dielectric constant (ε_r) 5, a current of 0.54 mA at 5 V, and an electrical conductivity of 1.88 × 10⁻⁵ Sm⁻¹. Owing to the above remarkable properties of the synthesized PDIDA, it holds potential applications in photovoltaics, fluorescence‐based detectors and n‐type channel field effect transistors, and so forth.

中文翻译：

光电活性发光缬氨酸取代的per二酰亚胺：通过光谱和密度泛函方法进行结构性质相关

在文献中，由于溶液相per二酰亚胺（PDI）半导体在溶剂中的溶解度有限，因此其适用性受到限制。相比之下，我们合成了一种高度可溶且新颖的缬氨酸官能化的PDI衍生物（im二酰亚胺二酸，PDIDA），其光学和电学性质已通过实验和密度泛函方法进行了仔细评估。值得注意的是，在缬氨酸取代中，以524 nm为中心的紫外可见吸收带归因于主要的HOMO electronic LUMO电子跃迁（称重系数= 99％）。有趣的是，实验证明了PDIDA中HOMO➔LUMO电子跃迁的吸收能量具有溶剂介电常数的不均匀变化（W形）。后者在计算上归因于更多的S ₁在S _o溶剂中稳定，尤其是在乙醇和二甲基亚砜（DMSO）中。此外，在525nm激发下，在533nm处观察到最大荧光发射，光致发光量子产率高达0.77。有趣的是，类似于吸收研究，溶剂极性对最大发射量有明显的影响，特别是在乙醇和DMSO中。随后，电化学研究证明，PDIDA保持固有的n型半导电性，介电常数（_εr）5，在5 V时的电流为0.54 mA，电导率为1.88×10 ^-5 Sm ^-1。由于合成的PDIDA具有上述非凡的特性，它在光电，基于荧光的检测器和n型沟道场效应晶体管等方面具有潜在的应用前景。

更新日期：2020-06-29

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