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Efficient energy transfer in phenyl-ethynyl-linked asymmetric BODIPY dimers
Tetrahedron ( IF 2.1 ) Pub Date : 2020-08-19 , DOI: 10.1016/j.tet.2020.131515
Priyadarshine Hewavitharanage , Reuben Warshawsky , Sergiy V. Rosokha , Jason Vaal , Kelsey Stickler , Dmitriy Bachynsky , Neil Jairath

Three asymmetric boron dipyrromethene (BODIPY) dimers were synthesized via coupling of a BODIPY monomer with a meso-phenyl ethynyl group substituent to the different monomers with an iodine atom at the second position of the BODIPY core. The dimers were characterized by 1H, 13C, and 11B, 19F NMR spectroscopy and high-resolution mass spectrometry. Density functional theory calculations show minimal conjugation between the two BODIPY units in the dimers due to a large dihedral angle between the BODIPYs and the linker. Absorption and fluorescence measurements of monomeric and dimeric compounds in dichloromethane indicated highly efficient singlet-singlet energy transfer between two BODIPY units (in which the meso-phenyl containing BODIPY unit act as the donor while the other BODIPY unit is the acceptor) and large Stokes shifts. In particular, the dimer with the styryl BODIPY unit absorbs light in a wide range of the spectrum (325 nm–690 nm) with emission in the near IR region. The ethynyl thiophene linked dimer showed the highest fluorescence quantum yield (76%) of all three dimers investigated in this study.



中文翻译:

苯乙炔基连接的不对称BODIPY二聚体中的有效能量转移

3个不对称硼二吡咯亚甲基(BODIPY)二聚体经由与一个BODIPY单体的偶联合成内消旋-苯基乙炔基取代基不同的单体与在BODIPY芯的第二位置碘原子。二聚体的特征是1 H,13 C和11 B,19F NMR光谱和高分辨率质谱。密度泛函理论计算显示,由于BODIPY与连接基之间的大二面角,二聚体中两个BODIPY单元之间的共轭最小。二氯甲烷中单体和二聚体化合物的吸收和荧光测量表明,两个BODIPY单元之间的高效单线态-单态能量转移(其中含内消旋苯基的BODIPY单元充当供体,另一个BODIPY单元充当受体)和大的斯托克斯位移。特别是,带有苯乙烯基BODIPY单元的二聚体吸收光谱范围很广的光(325 nm–690 nm),并在近红外区域发射光。乙炔基噻吩连接的二聚体显示了该研究中所有三个二聚体中最高的荧光量子产率(76%)。

更新日期:2020-09-30
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