Bardi Brunella, Vygranenko Katerina V, Koszarna Beata, Vakuliuk Olena, Dobrzycki Łukasz, Gryko Daniel T, Terenziani Francesca, Painelli Anna
Department of Chemistry, Life Sciences and Environmental Sustainability, University of Parma, Parco Area delle Scienze 17/a, 43124, Parma, Italy.
Institute of Organic Chemistry Polish Academy of Sciences, Warsaw, Poland.
Chemistry. 2023 Aug 10;29(45):e202300979. doi: 10.1002/chem.202300979. Epub 2023 Jul 13.
A new, transformative method for the preparation of rhodols and other merocyanines from readily available tetrafluorohydroxybenzaldehyde and aminophenols has been developed. It is now possible to prepare merocyanines bearing three fluorine atoms and additional conjugated rings, and the whole one-pot process occurs under neutral, mild conditions. Three heretofore unknown merocyanine-based architectures were prepared using this strategy from aminonaphthols and 4-hydroxycoumarins. The ability to change the structure of original rhodol chromophore into π-expanded merocyanines translates to a comprehensive method for the modulation of photophysical properties, such as shifting the absorption and emission bands across almost the entire visible spectrum, reaching a huge Stokes shift i. e. 4800 cm , brightness approximately 80.000 M cm , two-photon absorption cross-section above 150 GM and switching-on/off solvatofluorochromism. A detailed investigation allowed to rationalize the different spectroscopic behavior of rhodols and new merocyanines, addressing solvatochromism and two-photon absorption.
已开发出一种全新的、具有变革性的方法，可从易于获得的四氟羟基苯甲醛和氨基酚制备玫红染料及其他部花青染料。现在能够制备带有三个氟原子和额外共轭环的部花青染料，且整个一锅法过程在中性、温和的条件下进行。使用该策略，从氨基萘酚和4 - 羟基香豆素制备了三种此前未知的基于部花青染料的结构。将原始玫红染料发色团的结构转变为π扩展部花青染料的能力转化为一种用于调节光物理性质的综合方法，例如使吸收和发射带几乎在整个可见光谱范围内移动，实现高达4800 cm⁻¹的巨大斯托克斯位移、约80,000 M⁻¹ cm⁻¹的亮度、高于150 GM的双光子吸收截面以及开启/关闭溶剂化荧光变色。详细研究使我们能够合理地解释玫红染料和新部花青染料不同的光谱行为，包括溶剂化变色和双光子吸收。
