Synthesis and Properties of Heavy Chalcogen Analogues of the Texas Reds and Related Rhodamines.
Synthesis and Properties of Heavy Chalcogen Analogues of the Texas Reds and Related Rhodamines.
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DOI：
10.1021/om500346j
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发表时间：
2014-05-27
期刊：
影响因子：
2.8
通讯作者：
Detty MR
中科院分区：
文献类型：
--
作者：
Kryman MW;Schamerhorn GA;Hill JE;Calitree BD;Davies KS;Linder MK;Ohulchanskyy TY;Detty MR
在适当的硫基氧杂蒽酮前体中加入芳基格氏试剂，制备了得克萨斯红的类似物，其中包含了重硫原S、Se和Te原子。通过酰胺前体定向金属化、二硫族亲电试剂的加入以及氯氧磷和三乙胺的亲电环反应制备了山酮类化合物。德克萨斯红色类似物包含两个含有罗丹明氮原子的熔融julolidine环。还制备了含有两个“半julolidine”基团（一个三甲基四氢喹啉）和一个julolidine和一个“半julolidine”的类似物。研究了德克萨斯红类似物的光物理性质。s -类似物具有高荧光性，se -类似物在辐照下能高效生成单氧（1O2）， te -类似物易氧化为碲氧化态罗丹明。碲氧化二胺吸收波长≥690nm，最大荧光发射波长为bbb2020nm。一种定位于Colo-26细胞（小鼠结肠癌细胞系）线粒体中的甲三甲基取代的碲罗丹明衍生物，在体外被氧化为荧光碲氧化物。
Analogues of Texas red incorporating the heavy chalcogens S, Se, and Te atoms in the xanthylium core were prepared from the addition of aryl Grignard reagents to appropriate chalcogenoxanthone precursors. The xanthones were prepared via directed metalation of amide precursors, addition of dichalcogenide electrophiles, and electrophilic cyclization of the resulting chalcogenides with phosphorus oxychloride and triethylamine. The Texas red analogues incorporate two fused julolidine rings containing the rhodamine nitrogen atoms. Analogues containing two “half-julolidine” groups (a trimethyltetrahydroquinoline) and one julolidine and one “half-julolidine” were also prepared. The photophysics of the Texas red analogues were examined. The S-analogues were highly fluorescent, the Se-analogues generated single oxygen (1O2) efficiently upon irradiation, and the Te-analogues were easily oxidized to rhodamines with the telluroxide oxidation state. The tellurorhodamine telluroxides absorb at wavelengths ≥690 nm and emit with fluorescence maxima >720 nm. A mesityl-substituted tellurorhodamine derivative localized in the mitochondria of Colo-26 cells (a murine colon carcinoma cell line) and was oxidized in vitro to the fluorescent telluroxide.
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影响因子：
3.7
作者：
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通讯作者：
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影响因子：
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影响因子：
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作者：
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