Quinoline-containing, conjugated poly(aryleneethynylene)s:: Novel metal and H+-responsive materials
Quinoline-containing, conjugated poly(aryleneethynylene)s:: Novel metal and H+-responsive materials
复制标题
DOI：
10.1021/ma0116654
复制
发表时间：
2002-02-26
期刊：
影响因子：
5.5
通讯作者：
Bunz, UHF
中科院分区：
文献类型：
--
作者：
Bangcuyo, CG;Rampey-Vaughn, ME;Bunz, UHF
我们描述了新的共聚物的合成含有喹啉，苯，和炔基团的Pd催化的Heck-Cassar Sonogashira-Hagihara反应。喹啉在氯仿中用碘、高碘酸钾和硫酸的混合物直接碘化得到3，6-二碘喹啉。将3，6-二碘喹啉与1，4-二乙炔基-2，5-二（2-乙基己基）苯偶联，并将3，6-二乙炔基喹啉与1，4-二碘-2，5-二（2-乙基己氧基）苯偶联。聚合物以良好至优异的产率形成，聚合度（P-n）为11至95，多分散性（M-w/M-n）为1.8至3.3。它们的光学性质（即，吸收和发射）显示出显著地依赖于质子的存在，并且在较小程度上依赖于金属阳离子。质子化后的荧光变化对于烷基和烷氧基取代的聚合物是不同的。在烷基情况下，质子化后观察到亮黄色荧光，而对于烷氧基情况，在添加聚合物浓度> 0.1 mg L-1的酸后，聚合物的荧光会被猝灭。
We describe the synthesis of novel copolymers containing quinoline, benzene, and alkyne groups by a Pd-catalyzed Heck-Cassar-Sonogashira-Hagihara reaction. Direct iodination of quinoline by a mixture of iodine, potassium periodate, and sulfuric acid in chloroform gives 3,6-diiodoquinoline. 3,6-Diiodoquinoline was coupled to 1,4-diethynyl-2,5-bis(2-ethylhexyl)benzene, and 3,6-diethynylquinoline was coupled to 1,4-diiodo-2,5-bis(2-ethylhexyloxy)benzene. The polymers formed in good-to-excellent yields with a degree of polymerization (P-n) ranging from 11 to 95 and polydispersities (M-w/M-n) from 1.8 to 3.3. Their optical properties (i.e., absorption and emission) were shown to be dramatically dependent upon the presence of protons and to a lesser extent metal cations. The change in fluorescence upon protonation is different for the alkyl- and alkoxy-substituted polymer. In the alkyl case bright yellow fluorescence is observed upon protonation, while for the alkoxy case the polymer's fluorescence is quenched upon addition of acid at polymer concentrations > 0.1 mg L-1.