Tetrahedron ( IF 2.1 ) Pub Date : 2021-08-02 , DOI: 10.1016/j.tet.2021.132369 Toshiaki Shimasaki 1 , Kurumi Kobayashi 1 , Takayuki Kitanou 2 , Tomohiro Oki 2 , Tenta Ishikawa 2 , Naoto Asano 2 , Tetsuo Iwanaga 2 , Naozumi Teramoto 1 , Mitsuhiro Shibata 1
3-(4-(Arylethynyl)phenyl)-7-(diethylamino)-2H-chromen-2-ones 1a‒1d were synthesized by Pd/Cu-catalyzed Sonogashira cross-coupling reactions. After the structural properties were examined by the X-ray crystal analysis, their photophysical properties including fluorescence properties in solid states were systematically studied. It was revealed that the pyrenyl derivative 1d showed high fluorescence quantum yield (ΦF = 0.87) in a THF solution, and that the phenyl derivative 1a exhibited an intense fluorescence (Φsolid = 0.15) even in a solid state. According to the TDDFT calculations, the HOMOs of compounds 1a and 1b are mainly located on the 3-(4-(arylethynyl)phenyl)-7-(diethylamino)-2H-chromen-2-one moieties, whereas on the aryl moieties for 1c and 1d. The electrochemical studies revealed that the compounds 1a and 1b underwent reversible 1e− oxidations.
中文翻译:
7-(二乙氨基)-3-(4-(芳乙炔基)苯基)-2H-chromen-2-ones作为强荧光材料的合成及光物理性质
通过Pd/Cu催化的Sonogashira交叉偶联反应合成了3-(4-(Arylethynyl)phenyl)-7-(diethylamino)-2 H - chromen -2-ones 1a ‒ 1d。通过X射线晶体分析检查结构特性后,系统地研究了它们的光物理特性,包括固态荧光特性。据透露,在芘衍生物1D显示出高荧光量子产率(Φ ˚F 在THF溶液= 0.87),并且所述苯基衍生物1A表现出强荧光(Φ固体 = 0.15),即使在固体状态。根据 TDDFT 计算,化合物1a的 HOMO和1B主要位于3-(4-(芳基乙炔基)苯基)-7-(二乙氨基)-2- ħ -色烯-2-酮基团,而在为芳基部分1C和1D。电化学研究表明,化合物1a和1b经历了可逆的 1e -氧化。