Phenothiazine versus Phenoxazine: Structural Effects on the Photophysical Properties of NIR-II AIE Fluorophores

Aggregation-induced emission (AIE) fluorophores with second near-infrared window (NIR-II) fluorescence are very promising for in vivo imaging because they emit fluorescence in an aggregated state and provide desirable imaging resolution and depth. Up to now, only a limited number of NIR-II AIE fluor...

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Bibliographic Details
Published in:ACS applied materials & interfaces 2020-09, Vol.12 (39), p.43466-43473
Main Authors: Li, Shun, Cheng, Tianyuan, Yin, Changfeng, Zhou, Sensen, Fan, Quli, Wu, Wei, Jiang, Xiqun
Format: Article
Language:English
Subjects:
Biological and Medical Applications of Materials and Interfaces
Fluorescence
Fluorescent Dyes - chemistry
Infrared Rays
Molecular Structure
Nanoparticles - chemistry
Oxazines - chemistry
Particle Size
Phenothiazines - chemistry
Photochemical Processes
Surface Properties
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Summary:Aggregation-induced emission (AIE) fluorophores with second near-infrared window (NIR-II) fluorescence are very promising for in vivo imaging because they emit fluorescence in an aggregated state and provide desirable imaging resolution and depth. Up to now, only a limited number of NIR-II AIE fluorophores have been developed. Therefore, synthesizing novel NIR-II AIE fluorophores and investigating structural effects on their photophysical properties are very important for the development of AIE probes. In this work, we synthesized two donor–acceptor–donor-type NIR fluorophores with emissions extending into the NIR-II window named DPTQ-PhPTZ and DPTQ-PhPXZ with phenothiazine (PTZ) and phenoxazine (PXZ) derivatives as the electron donors, respectively, and studied their photophysical properties via theoretical and experimental approaches as well as the properties in NIR-II in vivo imaging. The PTZ and PXZ moieties provided typical AIE characteristics. Despite the very similar chemical structures of PTZ and PXZ, DPTQ-PhPTZ and DPTQ-PhPXZ exhibited rather different photophysical properties, for example, compared to DPTQ-PhPTZ, DPTQ-PhPXZ had higher quantum yield (QY) both in solution and in the aggregated state and its QY was less sensitive to solvent polarity. After being coated with an amphiphilic copolymer F-127, the fluorophores maintained fluorescence, and the formed fluorescent polymer nanoparticles (NPs) had satisfactory tumor accumulation and biocompatibility, implying that they are applicable for in vivo tumor detection.
ISSN:1944-8244
1944-8252
DOI:10.1021/acsami.0c12773