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Synthesis and Solvatochromic Behavior of Zwitterionic Donor–Bridge–Acceptor Systems with Oligo(p-phenylene) Spacers
Organic Materials Pub Date : 2021-04-01 , DOI: 10.1055/s-0041-1725075
Irina Zharinova 1 , Nicolau Saker Neto 1 , Tze Cin Owyong 1 , Jonathan M. White 1 , Wallace W. H. Wong 1
Affiliation  

Oligo(p-phenylene)s with a donor phenol group and an acceptor pyridinium moiety separated by one and two p-phenylene units were synthesized by the linear iterative Suzuki–Miyaura coupling method using aryl nonaflates as effective coupling reagents. Zwitterionic forms of these push–pull molecules were generated upon deprotonation of the phenol leading to large redshifts in absorbance maxima. UV-vis absorbance studies also revealed strong dependence of the band position on solvent polarity: a smooth bathochromic shift can be observed with the decrease of the solvent polarity. The molecule with one p-phenylene bridging unit showed the strongest solvatochromic characteristics in the series, spanning the range of 167 nm while moving from polar water to less polar N,N-dimethylformamide. The magnitude of this shift was close to Reichardt's dye — one of the most solvatochromic organic dyes known.



中文翻译:

具有低聚(对亚苯基)间隔基的两性离子供体-桥-受体体系的合成和溶剂变色行为

寡(p亚苯基)与供体酚基和受体吡啶基部分被一个和两个分离的š p亚苯基单元,通过使用芳基全氟丁磺酸根作为有效的偶联试剂的线性迭代铃木-宫浦偶合方法合成的。这些推挽分子的两性离子形式是在苯酚去质子化时产生的,从而导致最大吸光度发生大的红移。紫外可见吸收研究还表明,谱带位置对溶剂极性有很强的依赖性:随着溶剂极性的降低,可以观察到平滑的红移。具有一个对苯撑架桥单元的分子在该系列中表现出最强的溶剂致变色特性,从极性水移动到极性较小时跨越167 nm的范围N,N-二甲基甲酰胺。这种变化的幅度接近于雷卡德(Reichardt)的染料,后者是已知的溶剂化度最高的有机染料之一。

更新日期:2021-04-01
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