Combinatorial Discovery of Full-Color-Tunable Emissive Fluorescent Probes Using a Single Core Skeleton, 1,2-Dihydropyrrolo[3,4-β]indolizin-3-one

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• 作者：Eunha Kim ; Minseob Koh ; Jihoon Ryu ; Seung Bum Park
• 刊名：Journal of the American Chemical Society
• 出版年：2008
• 出版时间：September 17, 2008
• 年：2008
• 卷：130
• 期：37
• 页码：12206-12207
• 全文大小：132K
• 年卷期：v.130,no.37(September 17, 2008)
• ISSN：1520-5126

文摘

We developed a novel fluorescent core skeleton, 1,2-dihydropyrrolo[3,4-β]indolizin-3-one, by complexity-generating one-pot reactions through 1,3-dipolar cyclization followed by oxidative aromatization. This fluorescent core skeleton can accommodate various wavelengths of emission maxima by changing the electronic properties of substituents, which was postulated by computational studies. The full-color-tunable emission maxima were achieved with a single core skeleton by changing the substituents using the combinatorial approach. These novel fluorophores have excellent photophysical and photochemical properties: moderate to excellent quantum yields, resistance to the photobleaching, pH-independent fluorescence, large Stokes shifts, druglike lipophilicity for membrane permeability, etc. Further, we successfully demonstrated the bioapplication of fluorophores B1 and B5 in the immunofluorescence for visualizing cellular compartments of HeLa cells.