Synthesis and photoluminescence properties of fluorine‐containing poly(phenylene vinylene) bearing hexafluorocyclopentene‐fused phenanthrene unit
Synthesis and photoluminescence properties of fluorine‐containing poly(phenylene vinylene) bearing hexafluorocyclopentene‐fused phenanthrene unit
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六氟环戊烯稠合菲单元含氟聚亚苯基亚乙烯基的合成及光致发光性能
DOI：
10.1002/pi.6291
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发表时间：
2021
影响因子：
3.2
通讯作者：
Agou Tomohiro
中科院分区：
文献类型：
--
作者：
Fukumoto Hiroki;Shiitsuka Kazuki;Yamada Keisuke;Yamada Shigeyuki;Konno Tsutomu;Kubota Toshio;Agou Tomohiro
1，2-二芳基六氟环戊烯（1）在光照（λ= 365 nm）下的分子内氧化光环化反应以中等产率提供了具有甲酰基的六氟环戊烯稠合菲（2）。通过Horner-Wadsworth-Emmons反应将2与（2，5-双（十二烷氧基）-1，4-亚苯基）双（亚甲基）二膦酸四乙酯共聚，以41%的产率得到含氟聚（亚苯基亚乙烯基），聚合物-2。为了比较，还类似地制备二苯基乙烯型共聚物聚合物-1。聚合物-1和聚合物-2的数均分子量分别为8900和3300 g mol-1。共聚物显示出较高的热稳定性，揭示了他们的热重分析。共聚物在二氯甲烷中的紫外-可见光谱在420 nm附近出现π-π* 跃迁峰，成膜样品的跃迁峰向长波方向移动约10 nm。聚合物-1和聚合物-2的光致发光光谱在CHCl 3中分别在542和560 nm处显示出峰，而聚合物-2的光致发光强度在固态下非常低，推测是由于聚合物分子的部分聚集。© 2021工业化学学会。
The intramolecular oxidative photocyclization of 1,2‐diarylhexafluorocyclopentene (1) under light irradiation (λ= 365 nm) provided hexafluorocyclopentene‐fused phenanthrene with formyl groups (2) in moderate yield. The copolymerization of2with tetraethyl(2,5‐bis(dodecyloxy)‐1,4‐phenylene)bis(methylene)diphosphonate by the Horner–Wadsworth–Emmons reaction gave a fluorine‐containing poly(phenylene vinylene), Polymer‐2, in 41% yield. For comparison, a diphenylethene‐type copolymer, Polymer‐1, was also prepared analogously. The number‐average molecular weights of Polymer‐1 and Polymer‐2 were 8900 and 3300 g mol−1, respectively. The copolymers showed high thermal stability, as revealed by their thermogravimetric analysis. UV–visible spectra of the copolymers in CHCl3showedπ–π* transition peaks at around 420 nm, and the peaks shifted to longer wavelengths byca10 nm for samples in film form. The photoluminescence spectra of Polymer‐1 and Polymer‐2 exhibited peaks at 542 and 560 nm in CHCl3, respectively, whereas the photoluminescence intensity of Polymer‐2 was very low in the solid state, presumably owing to the partial aggregation of the polymer molecules. © 2021 Society of Industrial Chemistry.