Please use this identifier to cite or link to this item: https://hdl.handle.net/10356/83068
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dc.contributor.authorGawale, Yogeshen
dc.contributor.authorAdarsh, Nagappanpillaien
dc.contributor.authorKalva, Sandeep Kumaren
dc.contributor.authorJoseph, Joshyen
dc.contributor.authorPramanik, Manojiten
dc.contributor.authorRamaiah, Danaboyinaen
dc.contributor.authorSekar, Nagaiyanen
dc.date.accessioned2017-05-15T04:08:30Zen
dc.date.accessioned2019-12-06T15:11:10Z-
dc.date.available2017-05-15T04:08:30Zen
dc.date.available2019-12-06T15:11:10Z-
dc.date.copyright2017en
dc.date.issued2017en
dc.identifier.citationGawale, 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.en
dc.identifier.issn0947-6539en
dc.identifier.urihttps://hdl.handle.net/10356/83068-
dc.description9 p.en
dc.description.abstractFour 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.en
dc.description.sponsorshipMOE (Min. of Education, S’pore)en
dc.description.sponsorshipNMRC (Natl Medical Research Council, S’pore)en
dc.description.sponsorshipMOH (Min. of Health, S’pore)en
dc.language.isoenen
dc.relation.ispartofseriesChemistry - A European Journalen
dc.rights© 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].en
dc.subjectDyes/pigmentsen
dc.subjectFluorescenceen
dc.titleCarbazole-Linked Near-Infrared Aza-BODIPY Dyes as Triplet Sensitizers and Photoacoustic Contrast Agents for Deep-Tissue Imagingen
dc.typeJournal Articleen
dc.contributor.schoolSchool of Chemical and Biomedical Engineeringen
dc.identifier.doi10.1002/chem.201605702en
dc.description.versionAccepted Versionen
dc.identifier.rims196103en
item.fulltextWith Fulltext-
item.grantfulltextopen-
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