Characterization of Push-Pull-Type Benzo[X]quinoline Derivatives (X = g or f): Environmentally Responsive Fluorescent Dyes with Multiple Functions
Characterization of Push-Pull-Type Benzo[X]quinoline Derivatives (X = g or f): Environmentally Responsive Fluorescent Dyes with Multiple Functions
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DOI：
10.1021/acs.joc.0c01878
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发表时间：
2020-10-16
影响因子：
3.6
通讯作者：
Karasawa，Satoru
中科院分区：
文献类型：
--
作者：
Fuchi，Yasufumi;Umeno，Tomohiro;Karasawa，Satoru
带有双三氟甲基和胺基的苯并[X]喹啉（X=gorf:BQX）衍生物被设计为推拉型荧光染料。通过2,7-二氨基萘合成BQX衍生物，得到直链型(BQL)和角型(BQA)结构异构体。六种给定 BQX 衍生物的单晶 X 射线结构表明，BQL 和 BQA 系列采用平面和碗形结构。有趣的是，在荧光光谱中，BQL 系列在极性溶剂中发出超过 700 nm 的近红外区域。基于与胺部分相关的可见吸收和碱性质，利用 BQX-HCl 盐的离子交换反应研究了氨响应性。通过利用环境响应荧光探针，使用 HeLa 和 3T3-L1 细胞通过共焦激光显微镜进行细胞成像，发射特定的脂滴。结果表明BQX衍生物具有多种功能，可在材料化学和生物化学等领域得到应用。
Benzo[X]quinoline (X =gorf:BQX) derivatives bearing bis-trifluoromethyl and amine groups have been designed as push–pull-type fluorescent dyes. Through the synthesis ofBQXderivatives from 2,7-diaminonaphthalene, linear-type (BQL) and angular-type (BQA) structural isomers were obtained. X-ray structures of single crystals from six givenBQXderivatives revealed that theBQLandBQAseries adopt planar- and bowl-shaped structures. In the fluorescence spectra, interestingly, theBQLseries emitted in the near-infrared region over 700 nm in polar solvents. Based on the visible absorptions and base properties related to the amine moiety, the ammonia responsiveness was investigated using an ion-exchange reaction by theBQX-HClsalt. By exploiting the environmentally responsive fluorescence probe, cell imaging through confocal laser microscopy was conducted using HeLa and 3T3-L1 cells, emitting specific lipid droplets. The results indicate thatBQXderivatives have multiple functions and may be applied in materials chemistry and biochemistry.