Chai Xiaoyun, Cui Xiaoyan, Wang Baogang, Yang Fan, Cai Yi, Wu Qiuye, Wang Ting
Department of Organic Chemistry, College of Pharmacy, Second Military Medical University, Shanghai 200433 (P.R. China).
Department of Chemistry, New York University, New York, New York 10003 (USA).
Chemistry. 2015 Nov 16;21(47):16754-8. doi: 10.1002/chem.201502921. Epub 2015 Sep 30.
Phosphorus has been successfully fused into a classic rhodamine framework, in which it replaces the bridging oxygen atom to give a series of phosphorus-substituted rhodamines (PRs). Because of the electron-accepting properties of the phosphorus moiety, which is due to effective σ*-π* interactions and strengthened by the inductivity of phosphine oxide, PR exhibits extraordinary long-wavelength fluorescence emission, elongating to the region above 700 nm, with bathochromic shifts of 140 and 40 nm relative to rhodamine and silicon-substituted rhodamine, respectively. Other advantageous properties of the rhodamine family, including high molar extinction coefficient, considerable quantum efficiency, high water solubility, pH-independent emission, great tolerance to photobleaching, and low cytotoxicity, stay intact in PR. Given these excellent properties, PR is desirable for NIR-fluorescence imaging in vivo.
磷已成功融合到经典的罗丹明骨架中，在该骨架中它取代了桥连氧原子，从而得到了一系列磷取代罗丹明（PRs）。由于磷部分具有吸电子特性，这归因于有效的σ*-π*相互作用，并通过氧化膦的诱导效应得到增强，PR表现出异常的长波长荧光发射，延伸至700 nm以上区域，相对于罗丹明和硅取代罗丹明，其红移分别为140和40 nm。罗丹明家族的其他有利特性，包括高摩尔消光系数、可观的量子效率、高水溶性、与pH无关的发射、对光漂白的高耐受性以及低细胞毒性，在PR中均得以保留。鉴于这些优异特性，PR适用于体内近红外荧光成像。
