School of Materials Science and Engineering, Harbin Institute of Technology, Harbin 150001, China and Tianjin Key Laboratory for Photoelectric Materials and Devices, School of Materials Science & Engineering, Tianjin University of Technology, Tianjin 300384, China.
Tianjin Key Laboratory for Photoelectric Materials and Devices, School of Materials Science & Engineering, Tianjin University of Technology, Tianjin 300384, China.
Org Biomol Chem. 2018 Nov 7;16(41):7609-7618. doi: 10.1039/c8ob01671b. Epub 2018 Oct 2.
The design, synthesis, and photophysical properties of organic fluorophores have attracted considerable research interest due to the utility of these compounds for various optoelectronic, analytical, and biological applications. In this study, we synthesized two novel π-extended red-emitting hybrid xanthene dyes, each of which has two spirolactone rings and combines a seminaphthofluorescein moiety and a seminaphthorhodafluor moiety in a single molecule. The photophysical properties of the dyes in methanol in the presence of acid, base, and metal cations were investigated. Mono-ring-opened seminaphthofluorescein and seminaphthorhodafluor forms of the dyes could be obtained by the addition of OH or H, respectively. Owing to the changes in the absorbance spectra of the mono-ring-opened forms induced by addition of H and OH, the dyes could perform simultaneously the functions of an XOR gate and an INHIBIT gate, with the absorbances at 510 and 560 nm as outputs, respectively, and could act as half-subtractors with H and OH as inputs. Furthermore, stepwise ring-opening could be induced by Hg ions in methanol. In water, the dyes existed in double-ring-opened forms that emitted deep-red fluorescence and were mitochondria-targetable, suggesting that these chromophores might be useful as fluorescence tracers in biological applications. Because the absorption and fluorescence properties of these fluorophores can be regulated via their two spirolactone rings, we expect that these compounds will find utility in various optoelectronic, analytical, and biological applications.
由于这些化合物在各种光电、分析和生物应用中的实用性，有机荧光团的设计、合成和光物理性质引起了相当大的研究兴趣。在这项研究中，我们合成了两种新型的π-扩展的红光发射杂化香豆素染料，每种染料都有两个螺内酯环，并将半萘荧光素部分和半萘罗丹明部分结合在单个分子中。研究了染料在甲醇中存在酸、碱和金属阳离子时的光物理性质。通过加入 OH 或 H，染料可以得到单环开环的半萘荧光素和半萘罗丹明形式。由于单环开环形式的吸收光谱因加入 H 和 OH 而发生变化，染料可以同时执行异或门和抑制门的功能，输出分别为 510nm 和 560nm 的吸收，并且可以作为半减法器，输入为 H 和 OH。此外，在甲醇中，Hg 离子可以诱导逐步开环。在水中，染料以双环开环形式存在，发出深红色荧光，并可靶向线粒体，表明这些生色团可能在生物应用中作为荧光示踪剂有用。由于这些荧光团的吸收和荧光性质可以通过它们的两个螺内酯环来调节，我们预计这些化合物将在各种光电、分析和生物应用中找到用途。
