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Synthesis and investigation of BODIPYs with restricted meso-8-aryl rotation
Journal of Porphyrins and Phthalocyanines ( IF 1.5 ) Pub Date : 2020-05-20 , DOI: 10.1142/s1088424619501967
Guanyu Zhang 1 , Maodie Wang 1 , Caroline Ndung’U 1 , Petia Bobadova-Parvanova 2 , Frank R. Fronczek 1 , Kevin M. Smith 1 , M. Graça H. Vicente 1
Affiliation  

Three BODIPYs bearing 1,3,5,7-tetramethyl substituents and a meso-8-aryl group were synthesized and investigated, both experimentally and computationally. The presence of the 1,7-methyl groups and of ortho-substituents on the meso-8-aryl ring prevent free rotation of the meso-8-aryl group, resulting in high fluorescence quantum yields. Substitution at the 2,6-positions of these BODIPYs with chlorine atoms causes pronounced red-shifted absorptions and emissions, and in the case of 2,6-dichloro-1,3,5,7-tetramethyl-8-(2,4,6-triphenylphenyl)-BODIPY 2c increases its fluorescence quantum yields to 0.93 in dichloromethane and 0.98 in toluene. The X-ray structure of 1,3,5,7-tetramethyl-8-(2,4,6-triphenylphenyl)-BODIPY shows increased deviation from planarity and smaller dihedral angle of the meso-8-aryl group compared with the meso-8-phenyl- and meso-8-mesityl-BODIPY analogs. The presence of 2,6-chlorine atoms was found to not significantly affect the rotational barriers of the meso-8-aryl-groups.

中文翻译:

具有限制meso-8-aryl旋转的BODIPY的合成和研究

三个带有 1,3,5,7-四甲基取代基的 BODIPY 和一个中观-8-芳基在实验和计算上进行了合成和研究。存在 1,7-甲基和- 上的取代基中观-8-芳环防止自由旋转中观-8-芳基,导致高荧光量子产率。用氯原子取代这些 BODIPY 的 2,6 位会导致明显的红移吸收和发射,在 2,6-dichloro-1,3,5,7-tetramethyl-8-(2,4 ,6-三苯基苯基)-BODIPY2c将其荧光量子产率提高到二氯甲烷中的 0.93 和甲苯中的 0.98。1,3,5,7-四甲基-8-(2,4,6-三苯基苯基)-BODIPY 的 X 射线结构显示出与平面度的偏差增加,二面角变小中观-8-芳基与中观-8-苯基-和中观-8-mesityl-BODIPY 类似物。发现 2,6-氯原子的存在不会显着影响旋转势垒中观-8-芳基。
更新日期:2020-05-20
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