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Synthesis and photophysical properties of conformationally restricted difluoroboron β-diketonate complexes of 1-indanone derivatives
Tetrahedron ( IF 2.1 ) Pub Date : 2020-07-31 , DOI: 10.1016/j.tet.2020.131457
César R. Monzón-González , Ricardo Corona-Sánchez , Wilmer E. Vallejo Narváez , Tomás Rocha-Rinza , María Elena Sánchez-Vergara , Rubén A. Toscano , Cecilio Álvarez-Toledano

A series of conformationally restricted difluoroboron β-diketonate complexes (BF2bdks) was easily synthesized from (Z)-2-(1-arylhydroxyliden)-1-indanone derivatives in good to excellent yields. These dyes displayed the lowest energy absorption maxima in the range of 370–408 nm and possess molar absorption coefficients (ε) ranging from 8000 to 47 000 M−1cm−1 in CH2Cl2. All the absorption spectra of the BF2bdks systems were red shifted (5–43 nm) as compared to the parent difluoroboron 1,3-diphenyl-β-diketonate complex (BF2dbm). Their emission maxima were centered on 406–432 nm and the fluorescence quantum yields (Φ) were in the range of 0.33–0.87, which are in all cases much higher than the found for BF2dbm. These observations demonstrate the effectiveness of improving the dye quantum yield by restricting the intramolecular C–C bond rotation.



中文翻译:

1-茚满酮衍生物的构象受限二氟硼β-二酮酸酯配合物的合成及光物理性质

从(Z)-2-(1-芳基羟基)-茚满酮衍生物可以容易地合成一系列构象受限的二氟硼β-二酮硼酸酯络合物(BF 2 bdks),收率良好。这些染料在370–408 nm范围内显示出最低的能量吸收最大值,并在CH 2 Cl 2中具有8000至47 000 M -1 cm -1的摩尔吸收系数(ε)。与母体二氟硼1,3-二苯基-β-二酮酸酯络合物(BF 2)相比,BF 2 bdks系统的所有吸收光谱都发生了红移(5-43 nm)。dbm)。它们的发射最大值集中在406–432 nm处,荧光量子产率(Φ)在0.33–0.87的范围内,在所有情况下均比BF 2 dbm的发现高得多。这些观察结果表明,通过限制分子内C–C键的旋转,可以提高染料量子产率。

更新日期:2020-08-28
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