3,4-Ethylenedioxythiophene in planarizable push-pull oligothiophenes
3,4-Ethylenedioxythiophene in planarizable push-pull oligothiophenes
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DOI：
10.1039/c3ob27471c
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发表时间：
2013-01-01
影响因子：
3.2
通讯作者：
Matile, Stefan
中科院分区：
文献类型：
--
作者：
Dal Molin, Marta;Matile, Stefan
本文报道了一种含1个3，4-乙二氧基噻吩环(EDOT)和支架中单股强扭曲的推拉式四硫杂环两亲化合物的设计、合成和评价。平面化的推拉型低聚硫吩类两亲分子作为概念上的创新荧光探针最近被引入，它们可以检测脂类双层膜的流动性和潜力。“超扭曲”EDOT探针对平坦化和有限转动自由度的响应分别是激发光谱中的红移和振动精细结构的变化。在溶液中，发现较弱的溶致变色性和明显的热致变色性。平坦化和受限的旋转自由度对脂类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感知，但仍有可能。
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.