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Synthesis of fluorescent polycarbonates with highly twisted N,N-bis(dialkylamino)anthracene AIE luminogens in the main chain.

ABSTRACT: A synthetic route to embed aggregation-induced-emission-(AIE)-active luminophores in polycarbonates (PCs) in various ratios is reported. The AIE-active monomer is based on the structure of 9,10-bis(piperidyl)anthracene. The obtained PCs display good film-forming properties, similar to those observed in poly(bisphenol A carbonate) (Ba-PC). The fluorescence quantum yield (Φ) of the PC with 5 mol% AIE-active monomer was 0.04 in solution and 0.53 in solid state. Moreover, this PC is also miscible with commercially available Ba-PC at any blending ratio. A combined analysis by scanning electron microscopy and differential scanning calorimetry did not indicate any clear phase separation. These results thus suggest that even engineering plastics like polycarbonates can be functionalized with AIE luminogens without adverse effects on their physical properties.

SUBMITTER: Sairi AS

PROVIDER: S-EPMC9066558 | biostudies-literature | 2019 Jul

REPOSITORIES: biostudies-literature

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Synthesis of fluorescent polycarbonates with highly twisted N,N-bis(dialkylamino)anthracene AIE luminogens in the main chain.

Sairi Amir Sharidan AS Kuwahara Kohei K Sasaki Shunsuke S Suzuki Satoshi S Igawa Kazunobu K Tokita Masatoshi M Ando Shinji S Morokuma Keiji K Suenobu Tomoyoshi T Konishi Gen-Ichi GI

RSC advances 20190712 38

A synthetic route to embed aggregation-induced-emission-(AIE)-active luminophores in polycarbonates (PCs) in various ratios is reported. The AIE-active monomer is based on the structure of 9,10-bis(piperidyl)anthracene. The obtained PCs display good film-forming properties, similar to those observed in poly(bisphenol A carbonate) (Ba-PC). The fluorescence quantum yield (Φ) of the PC with 5 mol% AIE-active monomer was 0.04 in solution and 0.53 in solid state. Moreover, this PC is also misc ...[more]

PMID: 35518854

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Project description:Image-guided photodynamic therapy (PDT) can realize highly precise and effective therapy via the integration of imaging and therapy, and has created high requirements for photosensitizers. However, the PDT modality usually utilizes conventional type II photosensitizers, resulting in unsatisfactory imaging and therapeutic outcomes due to aggregation-caused quenching (ACQ), "always on" fluorescence and strong oxygen dependence. Herein, we report the type I-based aggregation-induced emission (AIE) photosensitizer TCM-CPS with low oxygen dependence, near-infrared (NIR) emission and "off-on" fluorescence; in particular, it produces more reactive oxygen species (ROS) than commercially available Chlorin e6 and Rose Bengal. In the rational design of the AIE-based photosensitizer TCM-CPS, the strongly electron-donating carbazole unit and π-thiophene bridge distinctly extend the emission wavelength and decrease the autofluorescence interference in bio-imaging, and the hydrophilic pyridinium salt group guarantees good molecular dispersion and maintains the fluorescence-off state in the aqueous system to decrease the initial fluorescence background. Moreover, the strong donor-π-acceptor (D-π-A) character in TCM-CPS greatly separates the HOMO-LUMO distribution, enhancing the ROS generation, and TCM-CPS was constructed as a type I photosensitizer with the assistance of strong intramolecular charge transfer in the electron-rich anion-π+ structure. Based on its favorable hydrophilicity and photosensitivity, TCM-CPS was found to be a highly efficient free-radical ROS photogenerator for both visualizing cells using light-up NIR fluorescence and efficiently killing cancer cells upon light irradiation. The positively charged TCM-CPS could quickly bind to bacteria via electrostatic interactions to provide a light-up signal and kill bacteria at a low concentration. In the PDT treatment of bacteria-infected mice, the mice exhibited accelerated wound healing with low wound infection. Thus, the AIE-based type I photosensitizer TCM-CPS has great potential to replace commercially available photosensitizers in the image-guided PDT modality for the treatment of cancer and bacterial infection.

Dataset Information

Synthesis of fluorescent polycarbonates with highly twisted N,N-bis(dialkylamino)anthracene AIE luminogens in the main chain.

Publications

Synthesis of fluorescent polycarbonates with highly twisted <i>N</i>,<i>N</i>-bis(dialkylamino)anthracene AIE luminogens in the main chain.

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