MegaStokes BODIPY-triazoles as environmentally sensitive turn-on fluorescent dyes

MegaStokes BODIPY-triazoles as environmentally sensitive turn-on fluorescent dyes
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DOI:
10.1039/c3sc22166k
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发表时间:
2013-01-01
期刊:
影响因子:
8.4
通讯作者:
Chang, Young-Tae
Chang, Young-Tae
中科院分区:
化学1区
文献类型:
--
作者:
Er, Jun Cheng;Tang, Mui Kee;Chang, Young-Tae

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在铜催化叠氮烯环加成反应的基础上,采用温和的反应条件,在固相条件下合成了一类新型的三唑衍生物BODIPY。由此得到的BODIPY-三氮唑具有MegaStokes位移(高达160 nm)和显著的环境敏感量子产率增量,这表明它们具有作为开启荧光传感器的潜力。在120个化合物库中,我们确定BDC-9是一种对人血清白蛋白具有高灵敏度和显著物种选择性的荧光化学传感器。这些结果验证了MegaStokes BODIPY染料作为新的荧光载体用于开发环境敏感的荧光探针。
A novel class of triazole-derivatized BODIPY compounds have been synthesized on solid-phase by employing mild reaction conditions based on the copper-catalyzed azide-alkyne cycloaddition. The resulting BODIPY-triazoles exhibited MegaStokes shifts (up to 160 nm) and remarkable environmentally sensitive quantum yield increments that asserted their potential as turn-on fluorescent sensors. Out of a library of 120 compounds, we identified BDC-9 as a fluorescent chemosensor with high sensitivity and remarkable species-selectivity towards human serum albumin. These results validate MegaStokes BODIPY dyes as new fluorophores for the development of environmentally sensitive fluorescent probes.