Carbazole substituted boron dipyrromethenes
Carbazole substituted boron dipyrromethenes
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DOI：
10.1039/c4dt01160k
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发表时间：
2014-08-28
影响因子：
4
通讯作者：
Gupta, Iti
中科院分区：
文献类型：
--
作者：
Kesavan, Praseetha E.;Gupta, Iti
制备了n -丁基咔唑(1)的中位取代BODIPY并进行了衍生化反应。合成了二溴BODIPY 2、α -甲酰基BODIPY 3和β -甲酰基BODIPY 4。通过HRMS、NMR、紫外-可见吸收、电化学和荧光等技术对化合物进行了表征。求解了BODIPY 1及其二溴衍生物2的晶体结构。在这两个x射线结构中，中咔唑基团与双吡啶平面之间的二面角减小，表明两者之间的相互作用增加。在BODIPY核心上与n -丁基咔唑基团的中位取代产生了巨大的斯托克斯位移（111-168 nm），与中位芳基BODIPY相比，量子产率更高。荧光光谱法观察到所有化合物1-4都能有效地从咔唑单元转移到BODIPY核心。化合物1-4的CV研究表明，还原电位和氧化电位发生阳极转移，表明中咔唑基团影响了BODIPY核的电子性质，使其更容易还原。
meso-Substituted BODIPY with N-butylcarbazole (1) was prepared and derivatized. Dibromo BODIPY 2, alpha-formyl BODIPY 3 and beta-formyl BODIPY 4 were synthesized. All compounds were characterized by HRMS, NMR, UV-vis absorption, electrochemical and fluorescence techniques. The crystal structures of BODIPY 1 and its dibromo derivative 2 were also solved. In both the X-ray structures, the dihedral angle between the meso-carbazole group and the dipyrrin plane was decreased, suggesting the increased interaction between the two units. meso-Substitution with the N-butylcarbazole group on the BODIPY core rendered huge Stokes shifts (111-168 nm) and higher quantum yields as compared to meso-aryl BODIPY. An efficient energy transfer from the carbazole unit to the BODIPY core was observed by fluorescence spectroscopy for all the compounds 1-4. CV studies of compounds 1-4 showed anodic shifts of the reduction and oxidation potentials, suggesting that the meso-carbazole group is affecting the electronic properties of the BODIPY core and making them easier to reduce.