title: Near-Infrared Phosphorus-Substituted Rhodamine with Emission Wavelength above 700 nm for Bioimaging.
abstract: 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.
authors.affiliation: Department of Organic Chemistry, College of Pharmacy, Second Military Medical University, Shanghai 200433 (P.R. China).
authors.forename: Xiaoyun
authors.initials: X
authors.lastname: Chai
authors.affiliation: Department of Chemistry, New York University, New York, New York 10003 (USA).
authors.forename: Xiaoyan
authors.initials: X
authors.lastname: Cui
authors.affiliation: Department of Organic Chemistry, College of Pharmacy, Second Military Medical University, Shanghai 200433 (P.R. China).
authors.forename: Baogang
authors.initials: B
authors.lastname: Wang
authors.affiliation: Department of Organic Chemistry, College of Pharmacy, Second Military Medical University, Shanghai 200433 (P.R. China).|College of Pharmacy, Yantai University, Yantai, Shandong 264005 (P.R. China).
authors.forename: Fan
authors.initials: F
authors.lastname: Yang
authors.affiliation: Department of Organic Chemistry, College of Pharmacy, Second Military Medical University, Shanghai 200433 (P.R. China).|College of Pharmacy, Yantai University, Yantai, Shandong 264005 (P.R. China).
authors.forename: Yi
authors.initials: Y
authors.lastname: Cai
authors.affiliation: Department of Organic Chemistry, College of Pharmacy, Second Military Medical University, Shanghai 200433 (P.R. China).
authors.forename: Qiuye
authors.initials: Q
authors.lastname: Wu
authors.affiliation: Department of Organic Chemistry, College of Pharmacy, Second Military Medical University, Shanghai 200433 (P.R. China). wangting1983927@gmail.com.
authors.forename: Ting
authors.initials: T
authors.lastname: Wang
mesh_terms: D003952:Diagnostic Imaging; D005453:Fluorescence; D005456:Fluorescent Dyes / Q000737:chemistry*; D006863:Hydrogen-Ion Concentration; D015394:Molecular Structure; D010758:Phosphorus / Q000737:chemistry*; D012235:Rhodamines / Q000737:chemistry*; D012825:Silicon / Q000737:chemistry*; D013050:Spectrometry, Fluorescence; D013056:Spectrophotometry, Ultraviolet; D019265:Spectroscopy, Near-Infrared
chemical_list: D005456:Fluorescent Dyes; D012235:Rhodamines; D010758:Phosphorus; D012825:Silicon
keywords: bioimaging; near-infrared; phosphorus; redshifted emission; rhodamine