School of Chemistry, SFI Tetrapyrrole Laboratory, Trinity Biomedical Science Institute, Trinity College Dublin, The University of Dublin , 152-160 Pearse Street, Dublin 2, Ireland.
King Abdullah University of Science and Technology (KAUST) , KAUST Solar Center (KSC), Physical Sciences and Engineering Division (PSE), Material Science and Engineering Program (MSE), Thuwal 23955-6900, Saudi Arabia.
J Am Chem Soc. 2017 May 10;139(18):6282-6285. doi: 10.1021/jacs.7b00551. Epub 2017 May 1.
Heavy atom-free BODIPY-anthracene dyads (BADs) generate locally excited triplet states by way of photoinduced electron transfer (PeT), followed by recombination of the resulting charge-separated states (CSS). Subsequent quenching of the triplet states by molecular oxygen produces singlet oxygen (O2), which reacts with the anthracene moiety yielding highly fluorescent species. The steric demand of the alkyl substituents in the BODIPY subunit defines the site of O addition. Novel bis- and tetraepoxides and bicyclic acetal products, arising from rearrangements of anthracene endoperoxides were isolated and characterized. O generation by BADs in living cells enables visualization of the dyads distribution, promising new imaging applications.
重原子自由的 BODIPY-蒽二聚体 (BADs) 通过光诱导电子转移 (PeT) 生成局域激发三重态，随后复合生成的电荷分离态 (CSS)。随后，分子氧猝灭三重态生成单线态氧 (O2)，其与蒽部分反应生成高荧光物种。BODIPY 亚基中烷基取代基的空间位阻决定了 O 添加的位置。新型双环氧和四环氧以及源于蒽内过氧化物重排的双环缩醛产物被分离和表征。BADs 在活细胞中生成 O2 可使二聚体分布可视化，有望开拓新的成像应用。
