Circularly Polarized Luminescence of [6]Helicenes through Excited-State Intramolecular Proton Transfer,Helvetica Chimica Acta

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Circularly Polarized Luminescence of [6]Helicenes through Excited-State Intramolecular Proton Transfer
Helvetica Chimica Acta ( IF 1.5 ) Pub Date : 2022-02-17 , DOI: 10.1002/hlca.202100221
Dominik Göbel ₁ , Sandra Míguez-Lago ₂ , Maria Jose Ruedas-Rama ₃ , Angel Orte ₃ , Araceli González Campaña ₂ , Michal Juríček ₄

Affiliation

We present the concept of combining circularly polarized luminescence (CPL) and excited-state intramolecular proton transfer (ESIPT) features into a single molecule as a strategy to generate high-performance ESIPT-based CPL materials. For this purpose, a [6]helicene bearing two ESIPT structural units was synthesized using a double Suzuki–Miyaura reaction and a double C(sp²)−H hydroxylation approach. The photophysical properties of the doubly hydroxylated [6]helicene were studied in parallel with a non-hydroxylated [6]helicene control compound, revealing that the presence of a chiral [6]helicene unit results in a strong CPL response and the presence of the ESIPT units in a considerable red shift. The red-shifted emission along with the outstanding g_lum (≈10⁻²) and a large Stokes shift makes the doubly hydroxylated [6]helicene a promising candidate for use in optoelectronics.

中文翻译：

[6]螺旋烯通过激发态分子内质子转移的圆偏振发光

我们提出了将圆偏振发光 (CPL) 和激发态分子内质子转移 (ESIPT) 特征结合到单个分子中的概念，作为生成高性能 ESIPT 基 CPL 材料的策略。为此，使用双Suzuki-Miyaura反应和双 C(sp ² )-H 羟基化方法合成了带有两个 ESIPT 结构单元的 [6] 螺旋烯。双羟基化 [6] 螺烯的光物理性质与非羟基化 [6] 螺烯对照化合物平行研究，表明手性 [6] 螺烯单元的存在导致强烈的 CPL 响应和ESIPT 单位发生相当大的红移。红移发射以及出色的_亮度（≈10 ^-2）和大的斯托克斯位移使双羟基化的[6]螺旋烯成为用于光电子学的有希望的候选者。

更新日期：2022-02-17

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