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Near‐Infrared Phosphorus‐Substituted Rhodamine with Emission Wavelength above 700 nm for Bioimaging
Author(s) -
Chai Xiaoyun,
Cui Xiaoyan,
Wang Baogang,
Yang Fan,
Cai Yi,
Wu Qiuye,
Wang Ting
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201502921
Subject(s) - bathochromic shift , photobleaching , photochemistry , fluorescence , rhodamine , quantum yield , chemistry , rhodamine b , molar absorptivity , moiety , materials science , analytical chemistry (journal) , organic chemistry , photocatalysis , optics , physics , catalysis
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.