β-Furan-Fused bis(Difluoroboron)-1,2-bis((1H-pyrrol-2-yl)methylene)hydrazine Fluorescent Dyes in the Visible Deep-Red Region

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• 作者：Lin Zhou ; Defang Xu ; Huaizhi Gao ; Chao Zhang ; Fangfang Ni ; Wenqi Zhao ; Dandan Cheng ; Xingliang Liu ; Aixia Han
• 刊名：Journal of Organic Chemistry
• 出版年：2016
• 出版时间：September 2, 2016
• 年：2016
• 卷：81
• 期：17
• 页码：7439-7447
• 全文大小：529K
• 年卷期：0
• ISSN：1520-6904

文摘

Novel β-furan-fused bis(difluoroboron)-1,2-bis((1H-pyrrol-2-yl)methylene)hydrazine (BOPHY) fluorescent dyes (F-BOPHY1–3) were prepared through an efficient process, and their structures were confirmed by ¹H NMR spectroscopy, ¹³C NMR spectroscopy, MALDI-TOF HRMS, and element analysis. Their optical properties were then characterized by UV–vis absorption and photoluminescence (PL) spectroscopy. The UV–vis absorption and PL spectra of the dyes shifted to longer wavelengths relative to those of BOPHY because of the fusion of their furan rings, which extended π-conjugation of the molecules. All of the dyes exhibited large extinction coefficients (109700–12300 M^–1 cm^–1), deep-red fluorescence emission (646–667 nm), moderate fluorescence quantum yields (0.30–0.45), as well as high chemical stability and photostability in solution. These advantageous properties show that these compounds are important to the design of efficient long-wavelength fluorescent dyes and are suitable for various applications in biotechnology and materials science.