From nonconjugation to conjugation: novel meso-OH substituted dipyrromethanes as fluorescence turn-on Zn2+ probes

被引:27
作者
Ding, Yubin [1 ,2 ]
Li, Tong [1 ,2 ]
Li, Xin [3 ]
Zhu, Weihong [1 ,2 ]
Xie, Yongshu [1 ,2 ]
机构
[1] E China Univ Sci & Technol, Key Lab Adv Mat, Shanghai 200237, Peoples R China
[2] E China Univ Sci & Technol, Inst Fine Chem, Shanghai 200237, Peoples R China
[3] KTH Royal Inst Technol, Sch Biotechnol, Dept Theoret Chem & Biol, Stockholm, Sweden
关键词
OXIDATIVE CYCLIZATION; ENERGY-TRANSFER; COPPER(II) ION; ZINC IONS; SENSOR; CHEMOSENSORS; PORPHYRIN; EMISSION; DESIGN; MODULATION;
D O I
10.1039/c3ob40121a
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Most reported Zn2+ probes suffer from the interference of background fluorescence originated from the conjugated structures of commonly utilized fluorophores. In this work, three novel meso-hydroxyl group substituted dipyrromethanes DPMOH1-DPMOH3 were synthesized and found to be colourless and nonfluorescent due to the interruption of the conjugated p system by an sp(3) carbon between the two pyrrolic units. Interestingly, only the addition of Zn2+ to the solutions of DPMOH1-DPMOH3 promoted their oxidation to dipyrrin forms, and bright fluorescence "turn on" was observed due to the formation of corresponding dipyrrin complexes with the dipyrrin : zinc stoichiometry of 2 :1. Zn2+ detection mechanism was investigated by UV-Vis, fluorescence, H-1 NMR and HRMS analyses, which can be ascribed to the CHEF type fluorescence enhancement, resulting from good rigidity of the dipyrrin complexes. Hence, DPMOH1-DPMOH3 can be used as fluorescence turn-on Zn2+ probes with the advantage of no background fluorescence.
引用
收藏
页码:2685 / 2692
页数:8
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