870753-29-0Relevant articles and documents
Highly regioselective palladium-catalyzed domino reaction for post-functionalization of BODIPY
Wang, Sisi,Wang, Zhaoli,Gao, Hu,Jiang, Liang,Liu, Hui,Wu, Fan,Zhao, Yue,Chan, Kin Shing,Shen, Zhen
supporting information, p. 1758 - 1761 (2021/02/27)
A series of benzo[a]-fused BODIPYs and the corresponding isomeric naphthyl-BODIPYs have been synthesized through a facile one-pot palladium-catalyzed domino reaction of BODIPY precursors (2-bromo-BODIPYs) with diarylethynes,via“cis,cis” and “trans,cis” ad
Direct C–H amination of BODIPY core: Synthesis and spectroscopic properties
Wang, Yitong,Shi, Xiuguang,Yu, Chunyan,Zhou, Zhikuan,Gai, Lizhi,Lu, Hua
, (2020/02/22)
A facile and direct C–H amination reaction at the 3-positions of BODIPY core was proceeded with high regioselectivity upon treatment with various amines. Spectroscopic properties of the 3-aminoBODIPY were substantially modulated by electron-donating nitro
Structural control of the photodynamics of boron-dipyrrin complexes
Kee, Hooi Ling,Kirmaiery, Christine,Yu, Lianhe,Thamyongkit, Patchanita,Youngblood, W. Justin,Calder, Matthew E.,Ramos, Lavoisier,Noll, Bruce C.,Bocian, David F.,Scheldt, W. Robert,Birge, Robert R.,Lindsey, Jonathan S.,Holten, Dewey
, p. 20433 - 20443 (2008/10/09)
Boron-dipyrrin chromophpres containing a 5-aryl group with or without internal steric hindrance toward aryl rotation have been synthesized and then characterized via X-ray diffraction, static and time-resolved optical spectroscopy, and theory. Compounds with a 5-phenyl or 5-(4-terf-butylphenyl) group show low fluorescence yields (~0.06) and short excited-singlet-state lifetimes (~500 ps), and decay primarily (>90%) by nonradiative internal conversion to the ground state. In contrast, sterically hindered analogues having an o-tolyl or mesityl group at the 5-position exhibit high fluorescence yields (~0.9) and long excited-state lifetimes (~6 ns). The X-ray structures indicate that the phenyl or 4-terf-butylphenyl ring lies at an angle of ~60° with respect to the dipyrrin framework whereas the angle is ~80° for mesityl or o-tolyl groups. The calculated potential energy surface for the phenyl-substituted complex indicates that the excited state has a second, lower energy minimum in which the nonhindered aryl ring rotates closer to the mean plane of the dipyrrin, which itself undergoes some distortion. This relaxed, distorted excited-state conformation has low radiative probability as well as a reduced energy gap from the ground state supporting a favorable vibrational overlap factor for nonradiative deactivation. Such a distorted conformation is energetically inaccessible in a complex bearing the sterically hindered o-tolyl or mesityl group at the 5-position, leading to a high radiative probability involving conformations at or near the initial Franck-Condon form of the excited state. These combined results demonstrate the critical role of aryl-ring rotation in governing the excited-state dynamics of this class of widely used dyes.