Biocompatible Two-Photon Absorbing Dipyridyldiketopyrrolopyrroles for Metal-Ion-Mediated Self-Assembly Modulation and Fluorescence Imaging
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 adj...
| Main Authors: | , , , , , , , , , , , , |
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| Format: | Journal Article |
| Language: | English |
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2017
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| Online Access: | https://hdl.handle.net/10356/83448 http://hdl.handle.net/10220/42627 |
| _version_ | 1811679005649141760 |
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| author | He, Tingchao Gao, Yang Sreejith, Sivaramapanicker Tian, Xiaoqing Liu, Lin Wang, Yue Joshi, Hrishikesh Phua, Soo Zeng Fiona Yao, Song Lin, Xiaodong Zhao, Yanli Sun, Handong Grimsdale, Andrew Clive |
| author2 | School of Materials Science & Engineering |
| author_facet | School of Materials Science & Engineering He, Tingchao Gao, Yang Sreejith, Sivaramapanicker Tian, Xiaoqing Liu, Lin Wang, Yue Joshi, Hrishikesh Phua, Soo Zeng Fiona Yao, Song Lin, Xiaodong Zhao, Yanli Sun, Handong Grimsdale, Andrew Clive |
| author_sort | He, Tingchao |
| collection | NTU |
| description | 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. |
| first_indexed | 2024-10-01T03:02:17Z |
| format | Journal Article |
| id | ntu-10356/83448 |
| institution | Nanyang Technological University |
| language | English |
| last_indexed | 2024-10-01T03:02:17Z |
| publishDate | 2017 |
| record_format | dspace |
| spelling | ntu-10356/834482023-02-28T19:33:39Z Biocompatible Two-Photon Absorbing Dipyridyldiketopyrrolopyrroles for Metal-Ion-Mediated Self-Assembly Modulation and Fluorescence Imaging He, Tingchao Gao, Yang Sreejith, Sivaramapanicker Tian, Xiaoqing Liu, Lin Wang, Yue Joshi, Hrishikesh Phua, Soo Zeng Fiona Yao, Song Lin, Xiaodong Zhao, Yanli Sun, Handong Grimsdale, Andrew Clive School of Materials Science & Engineering School of Physical and Mathematical Sciences Dipyridyldiketopyrrolopyrroles Cell imaging 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. Accepted version 2017-06-08T06:47:08Z 2019-12-06T15:23:13Z 2017-06-08T06:47:08Z 2019-12-06T15:23:13Z 2016 Journal Article He, T., Gao, Y., Sreejith, S., Tian, X., Liu, L., Wang, Y., et al. (2016). Biocompatible Two-Photon Absorbing Dipyridyldiketopyrrolopyrroles for Metal-Ion-Mediated Self-Assembly Modulation and Fluorescence Imaging. Advanced Optical Materials, 4(5), 746-755. 2195-1071 https://hdl.handle.net/10356/83448 http://hdl.handle.net/10220/42627 10.1002/adom.201500755 en Advanced Optical Materials © 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. This is the author created version of a work that has been peer reviewed and accepted for publication by Advanced Optical Materials, WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. It incorporates referee’s comments but changes resulting from the publishing process, such as copyediting, structural formatting, may not be reflected in this document. The published version is available at: [http://dx.doi.org/10.1002/adom.201500755]. 27 p. application/pdf |
| spellingShingle | Dipyridyldiketopyrrolopyrroles Cell imaging He, Tingchao Gao, Yang Sreejith, Sivaramapanicker Tian, Xiaoqing Liu, Lin Wang, Yue Joshi, Hrishikesh Phua, Soo Zeng Fiona Yao, Song Lin, Xiaodong Zhao, Yanli Sun, Handong Grimsdale, Andrew Clive Biocompatible Two-Photon Absorbing Dipyridyldiketopyrrolopyrroles for Metal-Ion-Mediated Self-Assembly Modulation and Fluorescence Imaging |
| title | Biocompatible Two-Photon Absorbing Dipyridyldiketopyrrolopyrroles for Metal-Ion-Mediated Self-Assembly Modulation and Fluorescence Imaging |
| title_full | Biocompatible Two-Photon Absorbing Dipyridyldiketopyrrolopyrroles for Metal-Ion-Mediated Self-Assembly Modulation and Fluorescence Imaging |
| title_fullStr | Biocompatible Two-Photon Absorbing Dipyridyldiketopyrrolopyrroles for Metal-Ion-Mediated Self-Assembly Modulation and Fluorescence Imaging |
| title_full_unstemmed | Biocompatible Two-Photon Absorbing Dipyridyldiketopyrrolopyrroles for Metal-Ion-Mediated Self-Assembly Modulation and Fluorescence Imaging |
| title_short | Biocompatible Two-Photon Absorbing Dipyridyldiketopyrrolopyrroles for Metal-Ion-Mediated Self-Assembly Modulation and Fluorescence Imaging |
| title_sort | biocompatible two photon absorbing dipyridyldiketopyrrolopyrroles for metal ion mediated self assembly modulation and fluorescence imaging |
| topic | Dipyridyldiketopyrrolopyrroles Cell imaging |
| url | https://hdl.handle.net/10356/83448 http://hdl.handle.net/10220/42627 |
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