Abstract The different oxidation states of sulphur atom play a significant role on functional materials. In this work, a aryl-thioether and its sulphone substituted benzo[c][1,2,5]oxadiazole dyes were synthesized and utilized to determine thiol-containing amino acids. The result of selectivity experiments showed they detected the cysteine and homocysteine under physiological condition with negligible interference from other amino acids. In comparison to the thioether dye, the sulphone-based dye exhibited much faster response time for Cys and Hcy. However, the sulphone restricted its thiol-reactivity and bioimaging performance in living cells. By reducing the oxidation state of sulphur atom, we amazedly found that the sulfoxide-based dye still maintained high selectivity ultrafast response time for Cys/Hcy under physiological condition. It was worth mentioning that it also had high reactivity and good bioimaging performance that sulfone compounds did not have.

中文翻译：

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苯并[c] [1,2,5]恶二唑染料的生物硫醇响应性能的调控和生物成像应用

摘要硫原子的不同氧化态在功能材料中起着重要作用。在这项工作中，合成了芳基硫醚及其砜取代的苯并[c] [1,2,5]恶二唑染料，并用于确定含硫醇的氨基酸。选择性实验的结果表明，他们在生理条件下检测到半胱氨酸和高半胱氨酸，而对其他氨基酸的干扰可忽略不计。与硫醚染料相比，基于砜的染料对Cys和Hcy的响应时间快得多。然而，砜限制了其在活细胞中的硫醇反应性和生物成像性能。通过降低硫原子的氧化态，我们惊奇地发现，在生理条件下，亚砜基染料仍保持对Cys / Hcy的高选择性超快响应时间。