Synthesis, Photophysical and Electrochemical Study of 1,3,6,8- Tetraarylsubstituted X-Shaped Phenanthrene Derivatives
Synthesis, Photophysical and Electrochemical Study of 1,3,6,8- Tetraarylsubstituted X-Shaped Phenanthrene Derivatives
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1,3,6,8-四芳基取代的X型菲衍生物的合成、光物理和电化学研究
DOI：
10.1002/ajoc.202100789
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发表时间：
2022
影响因子：
2.7
通讯作者：
Takeshi Kawase
中科院分区：
文献类型：
--
作者：
Jun-ichi Nishida;Kouhei Matsuno;Takeshi Kawase
以两种含溴和氯基的菲为原料，通过Suzuki偶联反应合成了含1，3，6，8位芳基的X形菲衍生物。含有4-丁基苯基、9，9-二甲基-9，9-二甲基-9，9-氟-2-基或4-二苯氨基苯基(DPAP)基团的X形菲在蓝光区域具有很强的发射性，其荧光效率随着芳基π偶联程度的增加而增加。为了研究1，8-和3，6-位上的给体(D)和受体(A)基团对分子内电荷转移发射的影响，合成了两个带有两个D-−D-基团和两个4-吡啶(Py)A-基团的D-DPAPA化合物。电化学研究结果表明，含有四个DPAP基团的菲在二氯甲烷中不发生氧化聚合，而同时具有DPAP和Py基团的两个D-−A类似物发生氧化聚合，生成具有电致变色性能的薄膜。
X‐shaped phenanthrene derivatives containing aryl substituents at the 1,3,6,8‐positions were synthesized through Suzuki coupling reactions of two types of phenanthrenes possessing bromine and chlorine substituents. X‐shaped phenanthrenes, with fourt‐butylphenyl, 9,9‐dimethyl‐9H‐fluoren‐2‐yl or 4‐diphenylaminophenyl (DPAP) groups, are highly emissive in the blue region and their fluorescence efficiencies increase as the extent of aryl π‐conjugation increases. To assess the effects of donor (D) and acceptor (A) groups at the 1,8‐ and 3,6‐positions on intramolecular charge‐transfer emission, two D−A compounds with two DPAP D‐groups and two 4‐pyridyl (Py) A‐groups were synthesized. Results of electrochemical studies reveal that the phenanthrene with four DPAP groups does not undergo oxidative polymerization in dichloromethane, but the two D−A analogs possessing both DPAP and Py groups do undergo oxidative polymerization, producing films which have electrochromic properties.