School of Chemistry and Biochemistry, Georgia Institute of Technology, 901 Atlantic Drive, Atlanta, GA 30332, USA.
Chemistry. 2011 Mar 7;17(11):3112-9. doi: 10.1002/chem.201002865. Epub 2011 Feb 21.
Two amphoteric cruciforms 6 and 7 (XF; 4,4'-[(1E,1'E)-(2,5-bis{[4-(dibutylamino)phenyl]ethynyl}-1,4-phenylene)bis(ethene-2,1-diyl)]diphenol, 4,4'-[{2,5-bis[(E)-4-(dibutylamino)styryl]-1,4-phenylene}bis(ethyne-2,1-diyl)]diphenol) were prepared by a Horner reaction followed by a Sonogashira coupling and subsequent deprotection. The XFs display significant changes in absorption and emission when exposed to trifluoroacetic acid, tetrabutylammonium hydroxide, and metal triflates. The substitution pattern of 6 and 7 leads to spatial separation of the frontier molecular orbitals, which allows the HOMO or LUMO of the XF to be addressed independently by acidic or basic agents. XF 6, which has hydroxyl groups on the styryl axis, displays changes in emission color upon exposure to ten amines in eight different solvents. The change in fluorescence upon the addition of amines was analyzed by linear discriminant analysis. These XFs may have potential in sensor applications for metal cations and amines.
两个两性十字形分子 6 和 7（XF；4,4'-[(1E,1'E)-(2,5-双{[4-(二丁基氨基)苯基]乙炔基}-1,4-亚苯基)双(乙烯-2,1-二基)]二苯酚，4,4'-[{2,5-双[(E)-4-(二丁基氨基)苯乙烯基]-1,4-亚苯基}双(乙炔-2,1-二基)]二苯酚)是通过 Horner 反应、Sonogashira 偶联反应和随后的脱保护反应制备的。XF 在暴露于三氟乙酸、四丁基氢氧化铵和金属三氟甲磺酸酯时，吸收和发射会发生显著变化。6 和 7 的取代模式导致前线分子轨道的空间分离，这使得 XF 的 HOMO 或 LUMO 可以分别被酸性或碱性试剂所寻址。XF 6 在苯乙烯轴上具有羟基，在八种不同溶剂中的十种胺存在下，其发射颜色会发生变化。通过线性判别分析对胺加入时荧光的变化进行了分析。这些 XF 可能在金属阳离子和胺的传感器应用中有潜在用途。
