Department of Organic Chemistry, University of Geneva, Geneva, Switzerland.
Org Biomol Chem. 2013 Mar 28;11(12):1952-7. doi: 10.1039/c3ob27471c. Epub 2013 Feb 7.
We report design, synthesis and evaluation of push-pull quaterthiophene amphiphiles containing one 3,4-ethylenedioxythiophene (EDOT) and a single strong twist in the scaffold. Planarizable push-pull oligothiophene amphiphiles have been introduced recently as conceptually innovative fluorescent probes that sense the fluidity and the potential of lipid bilayer membranes. The "hyper-twisted" EDOT probes respond to planarization and restricted rotational freedom with a red shift and changes in vibrational finestructure in the excitation spectrum, respectively. In solution, comparably weak solvatochromism and significant thermochromism are found. Planarization and restricted rotational freedom afford exquisite sensitivity toward nature and fluidity of lipid bilayer membranes, including ratiometric detection of phase transitions. The sensing of membrane potentials is weakened by these unique properties but remains possible.
我们报告了推拉四噻吩双亲化合物的设计、合成和评价，其中包含一个 3,4-亚乙基二氧噻吩（EDOT）和一个在支架中的单重强扭转。最近，可平面化的推拉齐聚噻吩双亲化合物作为概念创新的荧光探针被引入，用于感知脂质双层膜的流动性和潜力。“超扭曲”EDOT 探针分别通过平面化和限制旋转自由度，在激发光谱中产生红移和振动精细结构的变化来响应。在溶液中，发现相对较弱的溶剂化变色和显著的热致变色。平面化和限制旋转自由度使它们对脂质双层膜的性质和流动性具有极高的敏感性，包括对相变的比率检测。这些独特的性质削弱了对膜电位的检测，但仍然是可能的。
