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Synthesis of a triethylene glycol-capped benzo[1,2-c:4,5-c']bis[2]benzopyran-5,12-dione: A highly soluble dilactone-bridged p-terphenyl with a crankshaft architecture
Tetrahedron Letters ( IF 1.8 ) Pub Date : 2020-09-12 , DOI: 10.1016/j.tetlet.2020.152429
Justin J. Dressler , Eva M. Charlesworth-Seiler , Bart J. Dahl

3,10-Bis(triethylene glycol)benzo[1,2-c:4,5-c']bis[2]benzopyran-5,12-dione has been synthesized as an example of a dilactone-bridged p-terphenyl with a C2h crankshaft architecture that exhibits significant fluorescence. Lactone-bridged rotationally restricted p-terphenyl compounds are relatively unexplored, with the few known examples having very poor solubility and are therefore difficult to characterize and study. This superior TEG-solubilized analog has been shown to have much improved solubility, which should improve processability, and has attractive optical properties including efficient absorption in the near UV and significant emission of blue-violet light. Studies enabled by this TEG-solubilized crankshaft shaped molecule establishes that compounds with this architecture could be useful as pH-driven molecular switches with limited switching cycles or as “turn-off” sensors with instant fluorescence and UV absorption attenuation at high pH values.



中文翻译:

三乙二醇封端的苯并[1,2- c:4,5- c ']双[2]苯并吡喃-5,12-二酮的合成:具有曲轴结构的高可溶性双内酯桥连的三联苯

3,10-双(三乙二醇)苯并[1,2- c:4,5- c ']双[2]苯并吡喃-5,12-二酮已被合成为双内酯桥联的-三联苯并具有明显荧光的C 2h曲轴结构。内酯桥旋转限制p-三联苯化合物尚未得到充分开发,很少有已知的实例具有非常差的溶解性,因此难以表征和研究。已证明这种优异的TEG增溶类似物具有大大改善的溶解度,应改善加工性能,并具有吸引人的光学性能,包括在近紫外线下的有效吸收和蓝紫色光的大量发射。通过这种TEG增溶的曲轴形分子进行的研究表明,具有这种结构的化合物可用作具有有限的开关周期的pH驱动的分子开关,或可用作在高pH值下具有即时荧光和紫外线吸收衰减的“关闭”传感器。

更新日期:2020-10-06
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