Deciphering the Electronic Transitions of Thiophene‐Based Donor‐Acceptor‐Donor Pentameric Ligands Utilized for Multimodal Fluorescence Microscopy of Protein Aggregates,ChemPhysChem

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Deciphering the Electronic Transitions of Thiophene‐Based Donor‐Acceptor‐Donor Pentameric Ligands Utilized for Multimodal Fluorescence Microscopy of Protein Aggregates
ChemPhysChem ( IF 2.3 ) Pub Date : 2020-11-21 , DOI: 10.1002/cphc.202000669
Camilla Gustafsson ₁ , Hamid Shirani ₂ , Petter Leira ₃ , Dirk R Rehn ₁ , Mathieu Linares _{1,

4} , K Peter R Nilsson ₂ , Patrick Norman ₁ , Mikael Lindgren ₃

Affiliation

Anionic pentameric thiophene acetates can be used for fluorescence detection and diagnosis of protein amyloid aggregates. Replacing the central thiophene unit by benzothiadiazole (BTD) or quinoxaline (QX) leads to large emission shifts and basic spectral features have been reported [Chem. Eur. J. 2015, 21, 15133‐13137]. Here we present new detailed experimental results of solvent effects, time‐resolved fluorescence and examples employing multi‐photon microscopy and lifetime imaging. Quantum chemical response calculations elucidate how the introduction of the BTD/QX groups changes the electronic states and emissions. The dramatic red‐shift follows an increased conjugation and quinoid character of the π‐electrons of the thiophene backbone. An efficient charge transfer in the excited states S₁ and S₂ compared to the all‐thiophene analogue makes these more sensitive to the polarity and quenching by the solvent. Taken together, the results guide in the interpretation of images of stained Alzheimer disease brain sections employing advanced fluorescence microscopy and lifetime imaging, and can aid in optimizing future fluorescent ligand development.

中文翻译：

破译用于蛋白质聚集体多模态荧光显微镜的噻吩基供体-受体-供体五聚配体的电子跃迁

阴离子五聚噻吩乙酸酯可用于蛋白质淀粉样蛋白聚集体的荧光检测和诊断。用苯并噻二唑 (BTD) 或喹喔啉 (QX) 取代中心噻吩单元会导致较大的发射位移，并且已报道了基本的光谱特征 [ Chem.欧元。 J. 2015 , 21 , 15133-13137]。在这里，我们展示了溶剂效应、时间分辨荧光的新详细实验结果以及采用多光子显微镜和寿命成像的示例。量子化学反应计算阐明了 BTD/QX 基团的引入如何改变电子态和发射。显着的红移伴随着噻吩主链的π电子的共轭和醌型特征的增加。与全噻吩类似物相比，激发态 S ₁和 S ₂的有效电荷转移使得它们对溶剂的极性和猝灭更加敏感。总而言之，这些结果指导使用先进的荧光显微镜和终生成像对染色的阿尔茨海默病脑切片图像进行解释，并有助于优化未来的荧光配体开发。

更新日期：2020-11-21

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