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J Am Chem Soc. 2018 Feb 7;140(5):1715-1724. doi: 10.1021/jacs.7b10334. Epub 2018 Jan 27.

Donor Engineering for NIR-II Molecular Fluorophores with Enhanced Fluorescent Performance.

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Department of Materials Science & Engineering, Shenzhen Key Laboratory of Printed Organic Electronics, South University of Science & Technology of China , Shenzhen 518055, China.
Research Center for Advanced Materials and Biotechnology, Research Institute of Tsinghua University in Shenzhen , Shenzhen 518057, China.
Department of Chemistry, Tsinghua University , Beijing 100084, China.
State Key Laboratory of Precision Spectroscopy, School of Physics and Materials Science, East China Normal University , Shanghai 200062, China.
Department of Chemistry, Stanford University , Stanford, California 94305, United States.
School of Chemistry and Molecular Engineering, East China Normal University , Shanghai 200062, China.


Organic fluorophores have been widely used for biological imaging in the visible and the first near-infrared windows. However, their application in the second near-infrared window (NIR-II, 1000-1700 nm) is still limited mainly due to low fluorescence quantum yields (QYs). Here, we explore molecular engineering on the donor unit to develop high performance NIR-II fluorophores. The fluorophores are constructed by a shielding unit-donor(s)-acceptor-donor(s)-shielding unit structure. Thiophene is introduced as the second donor connected to the shielding unit, which can increase the conjugation length and red-shift the fluorescence emission. Alkyl thiophene is employed as the first donor connected to the acceptor unit. The bulky and hydrophobic alkyl thiophene donor affords larger distortion of the conjugated backbone and fewer interactions with water molecules compared to other donor units studied before. The molecular fluorophore IR-FTAP with octyl thiophene as the first donor and thiophene as the second donor exhibits fluorescence emission peaked at 1048 nm with a QY of 5.3% in aqueous solutions, one of the highest for molecular NIR-II fluorophore reported so far. Superior temporal and spatial resolutions have been demonstrated with IR-FTAP fluorophore for NIR-II imaging of the blood vessels of a mouse hindlimb.


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