A new far-red naphthorhodamine dye: Synthesis, fluorescent probe and bioimaging applications. (September 2016)

• Record Type: Journal Article
• Authors: Zhao, Yun; Ren, Yuehong; Li, Haoyang; Han, Taihe; Chen, Huanhuan; Guo, Wei
• Is Part Of: Dyes and pigments. Volume 132(2016)
• Page Start: 255
• Page End: 261
• Publication Date: 2016-09
• Subjects: Naphthorhodamine dye -- Fluorescent probe -- Mercury ion -- Cell imaging; Dyes and dyeing -- Periodicals; Pigments -- Periodicals; 667.2
• DOI: 10.1016/j.dyepig.2016.05.012
• Languages: English
• ISSNs: 0143-7208

Abstract

Abstract: A new extended-π-conjugated naphthorhodamine dye, 9′-diethylamino-2′-hydroxyl-benzo[ a ]fluoran (1 ) with a carboxylic acid-functional group was designed and synthesized. Compared to Rhodamine B, the emission wavelength of1 was extended to ca. 600 nm, and its fluorescence properties could be controlled by the key carboxylic acid-functional group. By taking advantage of1, we synthesized a new far-red bioimaging dye 2-ethyl-9′-diethylimino-2′-hydroxyl- benzo[ a ]fluoran (2 ) by esterification of1, which could selectively stain mitochondria. Moreover, encouraged by the spirocyclization switching mechanism platform, we successfully constructed a new fluorescent probe 9′-diethylamino-2′-hydroxyl-benzo[ a ]fluoran hydrazine (3 ), the hydrazide derivative of1, for Hg 2+ with good selectivity. These results suggest that the new naphthorhodamine dye could be used as a platform to construct fluorescent probes and bioimaging reagents. Graphical abstract: Highlights: A new π-conjugation extended naphthorhodamine dye1 with a carboxylic acid-functional group was designed and synthesized. The single crystal of1 was obtained and characterized. The photochemical properties of the dye were investigated in different solvent polarity. The dye was successfully used to construct a new fluorescent probe and a biomarker.