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Biocompatible Two‐Photon Absorbing Dipyridyldiketopyrrolopyrroles for Metal‐Ion‐Mediated Self‐Assembly Modulation and Fluorescence Imaging
Author(s) -
He Tingchao,
Gao Yang,
Sreejith Sivaramapanicker,
Tian Xiaoqing,
Liu Lin,
Wang Yue,
Joshi Hrishikesh,
Phua Soo Zeng Fiona,
Yao Song,
Lin Xiaodong,
Zhao Yanli,
Grimsdale Andrew C.,
Sun Handong
Publication year - 2016
Publication title -
advanced optical materials
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 2.89
H-Index - 91
ISSN - 2195-1071
DOI - 10.1002/adom.201500755
Subject(s) - materials science , fluorescence , covalent bond , metal ions in aqueous solution , photochemistry , absorption (acoustics) , two photon absorption , ion , tetrahydrofuran , nanoparticle , nanotechnology , metal , organic chemistry , optics , chemistry , laser , physics , metallurgy , solvent , composite material
Diketopyrrolopyrrole (DPP) derivatives are very promising nonlinear optical dyes with excellent thermal resistance and light stability. However, to the best of our knowledge, the fabrication of their organic micro‐ and/or nanostructures through covalent and/or noncovalent interactions to further adjust their corresponding two‐photon absorption (TPA) is rarely reported. In this work, based on previous synthesis method of pyridine‐containing ketopyrrolopyrroles, three dipyridyldiketopyrrolopyrroles (dipyridylDPPs) 1 , 2, and 3 containing 2‐, 3‐, and 4‐pyridyl substituents, respectively, have been prepared, which exhibit strong orange fluorescence and large TPA action cross‐sections in both organic (tetrahydrofuran) and aqueous media. Importantly, fluorescent organic nanoparticles (FONs) of the di(2‐pyridyl)DPP 1 prepared by the reprecipitation method displays strong two‐photon emission. Meanwhile, the FONs of 1 not only exhibit Ag + ions mediated self‐assembly modulation, but also display low cytotoxicity and allow two‐photon bioimaging in HeLa cells.