Small Panchromatic and NIR Absorbers from Quinoid Zwitterions,Organic Letters

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Small Panchromatic and NIR Absorbers from Quinoid Zwitterions
Organic Letters ( IF 4.9 ) Pub Date : 2020-09-29 , DOI: 10.1021/acs.orglett.0c02926
Angélina Torres Ruiz ₁ , Manon H. E. Bousquet ₂ , Simon Pascal ₁ , Gabriel Canard ₁ , Valérie Mazan ₃ , Mourad Elhabiri ₃ , Denis Jacquemin ₂ , Olivier Siri ₁

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The transamination of oxoaminobenzoquinonemonoimine (BQI derivatives), an unconventional zwitterionic quinone, allows isolation of a series of compounds featuring electron-donating aryl auxochromes. The substitution has a very strong impact on the electrochemical and optical features, which is rationalized by theoretical calculations. Protonation and alkylation of the BQIs toward the corresponding cations lead to surprising red-shifts of the absorption, especially in the instance of the most electron-rich dyes that exhibit panchromatic absorption spanning up to the near-infrared (NIR) region, a remarkable achievement for such small molecules.

中文翻译：

醌型两性离子的小型全色和近红外吸收剂

氧氨基苯并醌单亚胺（BQI衍生物）（一种非常规的两性离子醌）的氨基转移可分离出一系列具有供电子性芳族辅助色素的化合物。取代对电化学和光学特征有非常强烈的影响，这可以通过理论计算合理化。BQI向相应的阳离子质子化和烷基化会导致吸收发生令人惊讶的红移，尤其是在大多数电子富集的染料中，其全色吸收范围涵盖近红外（NIR）区域，这是一项了不起的成就对于这么小的分子。

更新日期：2020-10-17

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