Carbazole-Linked Near-Infrared Aza-BODIPY Dyes as Triplet Sensitizers and Photoacoustic Contrast Agents for Deep-Tissue Imaging
9 p.
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2017
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sg-ntu-dr.10356-830682023-12-29T06:47:52Z Carbazole-Linked Near-Infrared Aza-BODIPY Dyes as Triplet Sensitizers and Photoacoustic Contrast Agents for Deep-Tissue Imaging Gawale, Yogesh Adarsh, Nagappanpillai Kalva, Sandeep Kumar Joseph, Joshy Pramanik, Manojit Ramaiah, Danaboyina Sekar, Nagaiyan School of Chemical and Biomedical Engineering Dyes/pigments Fluorescence 9 p. Four new N-ethylcarbazole-linked aza-boron-dipyrromethene (aza-BODIPY) dyes (8 a,b and 9 a,b) were synthesized and characterized. The presence of the N-ethylcarbazole moiety shifts their absorption and fluorescence spectra to the near-infrared region, λ≈650–730 nm, of the electromagnetic spectrum. These dyes possess strong molar absorptivity in the range of 3–4×104 m−1 cm−1 with low fluorescence quantum yields. The triplet excited state and singlet oxygen generation of these dyes were enhanced upon iodination at the core position. The core-iodinated dyes 9 a,b showed excellent triplet quantum yields of about 90 and 75 %, with singlet oxygen generation efficiency of about 70 and 60 % relative to that of the parent dyes. Derivatives 8 a,b showed dual absorption profiles, in contrast to dyes 9 a,b, which had the characteristic absorption band of aza-BODIPY dyes. DFT calculations revealed that the electron density was spread over the iodine and dipyrromethene plane of 9 a,b, whereas in 8 a,b the electron density was distributed on the carbazole group and dipyrromethene plane of aza-BODIPY. The uniqueness of these aza-BODIPY systems is that they exhibit efficient triplet-state quantum yields, high singlet oxygen generation yields, and good photostability. Furthermore, the photoacoustic (PA) characteristics of these aza-BODIPY dyes was explored, and efficient PA signals for 8 a were observed relative to blood serum with in vitro deep-tissue imaging, thereby confirming its use as a promising PA contrast agent. MOE (Min. of Education, S’pore) NMRC (Natl Medical Research Council, S’pore) MOH (Min. of Health, S’pore) Accepted Version 2017-05-15T04:08:30Z 2019-12-06T15:11:10Z 2017-05-15T04:08:30Z 2019-12-06T15:11:10Z 2017 2017 Journal Article Gawale, Y., Adarsh, N., Kalva, S. K., Joseph, J., Pramanik, M., Ramaiah, D., et al. (2017). Carbazole-Linked Near-Infrared Aza-BODIPY Dyes as Triplet Sensitizers and Photoacoustic Contrast Agents for Deep-Tissue Imaging. Chemistry - A European Journal, 23(27), 6570-6578. 0947-6539 https://hdl.handle.net/10356/83068 http://hdl.handle.net/10220/42405 10.1002/chem.201605702 196103 en Chemistry - A European Journal © 2017 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 Chemistry - A European Journal, 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/chem.201605702]. application/pdf |
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English |
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Dyes/pigments Fluorescence |
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Dyes/pigments Fluorescence Gawale, Yogesh Adarsh, Nagappanpillai Kalva, Sandeep Kumar Joseph, Joshy Pramanik, Manojit Ramaiah, Danaboyina Sekar, Nagaiyan Carbazole-Linked Near-Infrared Aza-BODIPY Dyes as Triplet Sensitizers and Photoacoustic Contrast Agents for Deep-Tissue Imaging |
| description |
9 p. |
| author2 |
School of Chemical and Biomedical Engineering |
| author_facet |
School of Chemical and Biomedical Engineering Gawale, Yogesh Adarsh, Nagappanpillai Kalva, Sandeep Kumar Joseph, Joshy Pramanik, Manojit Ramaiah, Danaboyina Sekar, Nagaiyan |
| format |
Article |
| author |
Gawale, Yogesh Adarsh, Nagappanpillai Kalva, Sandeep Kumar Joseph, Joshy Pramanik, Manojit Ramaiah, Danaboyina Sekar, Nagaiyan |
| author_sort |
Gawale, Yogesh |
| title |
Carbazole-Linked Near-Infrared Aza-BODIPY Dyes as Triplet Sensitizers and Photoacoustic Contrast Agents for Deep-Tissue Imaging |
| title_short |
Carbazole-Linked Near-Infrared Aza-BODIPY Dyes as Triplet Sensitizers and Photoacoustic Contrast Agents for Deep-Tissue Imaging |
| title_full |
Carbazole-Linked Near-Infrared Aza-BODIPY Dyes as Triplet Sensitizers and Photoacoustic Contrast Agents for Deep-Tissue Imaging |
| title_fullStr |
Carbazole-Linked Near-Infrared Aza-BODIPY Dyes as Triplet Sensitizers and Photoacoustic Contrast Agents for Deep-Tissue Imaging |
| title_full_unstemmed |
Carbazole-Linked Near-Infrared Aza-BODIPY Dyes as Triplet Sensitizers and Photoacoustic Contrast Agents for Deep-Tissue Imaging |
| title_sort |
carbazole-linked near-infrared aza-bodipy dyes as triplet sensitizers and photoacoustic contrast agents for deep-tissue imaging |
| publishDate |
2017 |
| url |
https://hdl.handle.net/10356/83068 http://hdl.handle.net/10220/42405 |
| _version_ |
1787136539973648384 |